FLAVOURING MATERIALS
NATURAL AND SYNTHETIC
OXFORD TECHNICAL PUBLICATIONS
FLAVOURING
MATERIALS
NATURAL AND SYNTHETIC
BY
A. CLARKE, F.G.S.
CHEMIST AND TECHNICAL EXPERT TO MESSRS. GEO. BASSETT AND CO. LTD.
MESSRS. SAMUEL M. JOHNSON AND SONS, FTC.
LONDON
HENRY FROWDE AND HODDER & STOUGHTON
THE LANCET BUILDING
T BEDFORD STREET, STRAND, W.C. 2
First Printed 1022
MAIN LIBWARV.AQQICM: ..TURfE DEFT.
PRINTED IN GREAT BRITAIN BY MORRISON AND GIBB LIMITED, EDINBURGH
rv
PREFACE
THIS volume represents the accumulated notes of a
number of years during which the author has been
connected, in a chemical and technical capacity, with
the foodstuff and beverage trades. Several excellent
books are in existence which deal in a specialised
fashion with certain sections of flavouring materials, e.g.
essential oils; also a number of contemporary journals
deal regularly and systematically with many of the
products mentioned. It is intended, however, that the
notes gathered herein should form a work of reference,
of a more comprehensive type than has yet been
published, for the whole of foodstuff and beverage
manufacturers, many of whose flavouring materials are
drawn from widely varying sources.
Frequent reference to contemporary scientific litera-
ture is made in the text with a view to providing a
ready means of following up information dealing with
any special flavouring material.
A. C.
49893?
INTRODUCTION
THE SENSE OF TASTE
BEFORE commencing the treatment of the various sub-
stances which are used as flavouring agents it is proposed
briefly to describe the physiology of the sense of taste and
to indicate the importance of flavouring bodies in the
assimilation of food-stuffs.
Closely allied to the sense of taste is that of smell.
The two are frequently referred to as the " chemical senses "
because their excitation depends upon specific chemical
substances. In a great many cases, especially with
aromatic bodies, the two senses function together.
Experimentally, they may be readily divided. If the
sense of smell is suspended either by nasal catarrh or by
closing the nostrils many of the aromatic flavours cannot
be distinguished. The gustatory sense is, in fact, the most
uneducated and backward of the senses in the majority of
individuals. The influence of sight is also interesting in
this respect ; if the suggestion conveyed by the eyes is
removed, either by blindfolding the subject or by making
the object unusual in appearance, the sense of taste is
found to be very erratic.
The four primary or elementary tastes are sweet, bitter,
acid and saline, and it is usual for the taste organs of the
tongue to be able to distinguish these under any but very
abnormal circumstances. Most flavouring bodies are,
vii
Vlll
INTRODUCTION
however, of a compound character, having a tendency
towards one or more of the above primary tastes and con-
taining also some aromatic body, either of a volatile or
extractive nature. In dealing with such bodies the
combined faculties of taste and smell are required, but
commonly both are classified as taste.
FIG. 1 . Horizontal Section through the Mouth, showing Organs of Taste.
(1) Pharyngo-palatine arch, (2) glosso-epiglottic fold, (3) epiglottis, (4)
pharyngeal portion of tongue, (5) palatine tonsil, (6) vallate papillae,
(7) fungiform papillae, (8) raphe of tongue, (9) conical papillae. (After
Cunningham. )
The dorsal surface of the tongue is divided into two
distinct sections, as shown in Fig. 1, by a V-shaped row of
eight or nine large circumvallate papillae. The section
INTRODUCTION ix
extending from the vicinity of the V to the tip is covered
with mucous membrane containing innumerable tiny
papillae of the filiform and conical type, while dotted
all over the surface and especially at the sides of the
tongue are slightly larger papillae of the fungiform type.
Behind the lingual V at the base of the tongue are
lymphatic follicles and mucous glands which are specially
concerned with the sense of taste. Besides this area, the
soft palate, the anterior pillar of the fauces, the posterior
wall of the pharynx, the laryngeal surface of the epiglottis
and the inner area of the arytaenoid processes of the larynx
are endowed with varying degrees of the gustatory sense.
The tiny organs which were found by Loven and
Schwalbe, in 1867, to be the agencies which directly
registered the taste of a substance are contained chiefly in
the epithelial layers of the circumvallate and fungiform
papillae. They are also contained in the areas behind the
lingual V mentioned above. In shape each organ resembles
a flower-bud, of approximate measurements 80^ in height
and 40//, in breadth, the term " taste-buds " being usually
applied to them. The nerve fibres lie alongside and
between the epithelial cells of the taste-buds.
The taste-sense is not distributed evenly over the entire
surface of the tongue, and several workers, among them
Kiesow and Hanig, have spent considerable time in the
determination of the areas of the greatest sensibility.
Further, taking the simple tastes sweet, bitter, acid and
saline, it has been demonstrated that the areas of sensibility
vary with each. For example, it has been found that the
central area of the tongue is comparatively insensitive to
most tastes, but that the area of insensibility varies
according as to whether the substance applied to it is sweet,
bitter, acid or saline.
x INTRODUCTION
It has been established that the tip of the tongue is most
sensitive to sweet substances and that the base is least
sensitive. The sensibility diminishes gradually from the
tip to the base and from the sides inwards.
The base of the tongue, near the lingual V, is most
sensitive to bitter substances and the tip is the least
sensitive. From the base along the sides a rapid diminution
in sensibility occurs, while from the sides inwards a gradual
essening of perception is evident.
The maximum sensibility to acid has been shown to
occur about half-way down each side of the tongue, the
sensibility diminishing towards both tip and base. Also,
from the edges of the tongue inwards towards the central
insensitive area the sensibility to acid gradually diminishes.
The tip and edges of the tongue are most keenly
perceptive of saline substances, the base being least
sensitive. From the edges inwards the sensibility to salt
is fairly constant until the insensitive area is reached.
The sensibility of the taste-organs of the tongue may be
modified in many ways. For example, if the tongue is held
in iced water for ten minutes it is rendered insensitive to
most tastes other than those of an acid description. The
action of water at a temperature of 50 C. for a similar
length of time has the same effect. Kiesow demonstrated
that after treating the tongue with dilute solutions of
hydrochloric acid and salt distilled water gives a sweet
sensation on the tongue. Many other so-called contrast
sensations of this type have been noted. The temporary
suspension of the power of taste, for several or all of the
elementary tastes, is produced by treating the tongue with
certain substances, e.g. cocaine, eucaine-B, stovaine,
gymnenic acid, etc.
The organs upon which the human being is chiefly
INTRODUCTION
XI
dependent for an appreciation of aromatic substances are
illustrated in Fig. 2. The olfactory nerves terminate in
FIG. 2. View of the Lateral Wall of the Nose.
(1) Opening of anterior ethmoidal cells, (2) opening of middle ethmoi-
dal cells, (3) opening of posterior ethmoidal cells, (4) bull a ethmoid alls,
(5) hiatus semilunaris, (6) opening of maxillary sinus, (7) vestibule.
(After Cunningham.)
the mucous membrane of the upper portion of the two
nasal chambers, the nerve fibres being disseminated over
the upper portion of the cavity.
Many theories have been advanced regarding the
olfactory sense. One of the latest was propounded by
A. Durand at the Paris Academy of Sciences in January
1918. He stated that the sense of smell was dependent on
xii INTRODUCTION
the following conditions: the presence in the air of "ions
odorants " which are capable of aiding the condensation of
atmospheric moisture, a suitable amount of moisture in the
atmosphere and the cooling of the air current which is
produced by inspiration (see also Journ. Chem. Soc., 1918,
i./88 ; Perfumery and Essential Oil Record, 191*7, 8, 336 ;
1918, 9, 41).
A very interesting field of research, in which there is
still the opportunity for a vast amount of work, is that which
deals with the relation between chemical constitution and
the taste and smell of chemical compounds.
As a consequence of a research upon the chlorides,
bromides and iodides of lithium, sodium, potassium and
rubidium, Gley and Eichet in 1885 formed the opinion
that taste is a chemical effect because it takes place in
accordance with the ordinary laws of chemical reaction.
In 1888 Corin concluded as regards acids that the
intensity of the acid taste of a molecule of any acid is
dependent on the relation between the weight of the acidic
hydrogen which it is possible to substitute by a metal
contained in the molecule and the weight of that molecule.
Hober and Kiesow in 1898 investigated the possibility
of taste being due to free ions in molecules which are
capable of ionisation. They showed that the three
elementary tastes, sweet, bitter and saline, can be produced
by free ions and also that the compound tastes of various
bodies is the resultant sum of the tastes of their individual
components broken up by the dissociative action of the
water.
Haycraft in 1887, Sternberg in the period 1898 to 1903
and Herlitzka in 1908-9 attempted to determine the
relations between different tastes and the position of the
atoms or groups of atoms in the molecule ; most of the
INTRODUCTION xiii
researches were, however, carried out with inorganic
substances. Barrel and Eanc, in the Revue Scientifique,
Dec. 7, 1918, summarised the state of knowledge to that
date as regards sweet tastes, their conclusion being that
considerable ground remained to be covered before the
taste of a compound could be deduced with accuracy from
its molecular structure.
As regards smell, although several attempts have been
made to correlate the olfactory properties of bodies and
their chemical constitutions, not very much progress has
been achieved. In researches dealing with inorganic
compounds, Haycraft, Passy and Zwaardemaker demon-
strated, at different times, that the elements which give
odoriferous compounds belong almost entirely to the fifth,
sixth and seventh groups in the Periodic Classification of
Mendele'eff. Also, a definite periodicity occurs within each
series of compounds in the appearance of odorous and
non-odorous substances.
The comparatively recent development in the production
of synthetic odoriferous bodies has emphasised the fact
that in homologous series of organic compounds, e.g.
alcohols, acids, aldehydes, etc., there is frequently a regular
change, both in the intensity and quality of the odours, as
the series ascend.
The reader who wishes to pursue the study of recent
progress and thought on the classification of perfumes and
the correlation of odour and chemical constitution will find
the following references of interest : Odour and Constitu-
tion, Austerweil and Cochin, P. & E.O.R., August 1910 ;
Sense of Smell, Dr. E. Foerster, P. & E.O.R., September
1911 ; The Senses of Taste and Smell, A. Baudrexel,
P. & E.O.R., July 1914; Classification of Odours, E. J.
Parry, P. & E,O.R., May 1916 ; Odour and Constitution,
xiv INTRODUCTION
Dr. H. J. Prins, P. & E.O.R., July 1917 ; Constitution and
Odour, E. Marchand ; Chem. Abstr. Am. Chem. Soc., 1916,
10, 2383 ; and also Journ. Chem. Soc., 1921, L/637, 755.
The importance of flavouring compounds in the
assimilation of foodstuffs is at once apparent when the
fact is realised that the digestion of food depends to a
considerable extent upon its palatableness. It has been
demonstrated that food which is relished and which
stimulates the appetite is usually digested with much
greater ease than that which is insipid and flavourless.
The over-flavouring of foodstuffs is, of course, an evil
practice in that it weakens the perception of the gustatory
and olfactory senses for the more delicate flavours.
CONTENTS
PAGE
INTRODUCTION : THE SENSE OF TASTE vii
SECTION I
SPICES, CONDIMENTS AND MISCELLANEOUS
VEGETABLE AND ANIMAL FLAVOURING
BODIES
CHAPTER I
SPICES AND CONDIMENTS ..... 1
Allspice Caraway Cardamoms Cinnamon and Cassia
Cloves Coriander Ginger Mustard Nutmeg and
Mace Pepper Red Pepper and Cayenne Pepper.
CHAPTER II
ADULTERANTS OF SPICES AND CONDIMENTS . .22
Nut, Cocoa and Cocoanut Shells Grain Hulls Clove
Stems Date and Olive Stones Linseed Meal Wood
Flours Farinaceous and Leguminous Flours Turmeric.
CHAPTER III
ANALYTICAL METHODS ..... 28
General Methods: Moisture Ash Ether Extract-
Alcohol Extract Starch Crude Fibre Nitrogen
Micro-examination.
Special Methods : Cloves Ginger Mace Mustard-
Pepper.
xvi CONTENTS
CHAPTER IV
PAGE
MISCELLANEOUS FLAVOURING MATERIALS . . .34
Vegetable Bodies : Agaric Aloes Angelica Root
Angostura Bark Anise Arnica Balm Buckbean
Burdock Calamus Calisaya Caroba Cascarilla
Celery Seeds Centaury Chiretta Colocynth Columba
Cubebs Dandelion Elder Flowers Elecampane
Fennel Galanga Garlic Gentian Ginseng G uaiac
Wood Holy Thistle Hops Horehound Hyssop
Juniper Kola Laurel Lavender Liquorice Lovage
Manna Marjoram Musk Seeds Orris Root
Paradise Grains Pellitory Root Peppermint Poly-
pody Pomegranate Prickly Ash Pyrethrum Root
Quassia Red Peruvian Bark Rhubarb Roman
Chamomile Rosemary Sage Sarsaparilla Sassafras
Saxifrage Senega Senna Simaruba Bark Squaw
Vine Tamarinds Tansy Thyme Tonka Beans
Valerian Vanilla Virginia Snake Root White Cin-
namon Wild Cherry Bark Woodruff Wormwood
Yarrow Zedoary Root Balsams, etc. : Benzoin
Peru Balsam Styrax Tolu. Animal Products :
Ambergris Castoreum Civet Musk.
SECTION II
ESSENTIAL OILS
CHAPTER V
THE PREPARATION AND ANALYSIS OF ESSENTIAL OILS . 58
Preparation Distillation Extraction Expression
General Analytical Methods. Physical Tests : Con-
gealing-Point Melting-Point Boiling- Point. Chemical
Tests (General Methods): Esters Acid Value
Saponification Value Alcohols Aldehydes Ketones
Phenols Adulterants. Special Methods : Citral
Cineol Phellandrene Citronellal Geraniol Prussic
Acid Benzaldehyde Lead in Cassia Oil.
CONTENTS xvii
CHAPTER VI
PAGE
SYSTEMATIC SURVEY OF THE CHIEF ESSENTIAL OILS . 70
Coniferae : Cedar, Juniper, Pine Needle, Turpentine.
Gramineae : Citron ella, Ginger-grass, Lemon-grass, Palma-
rosa, Veti-vert.
Monocotyledons : Aroideae : Calamus Oil. Iridaceae :
Orris. Liliaceae : Garlic and Onion. Zingiberaceae :
Cardamom, Curcuma (Turmeric), Galanga, Ginger, Grains
of Paradise, Zedoary.
Dicotyledons : Anonaceae : Cananga, Ylang-ylang.
Betulaceee : Wintergreen. Burseraceae : Elemi, Lignaloe,
Myrrh. Cannabinaceae : Hops Compositae : Arnica,
Chamomile, Tansy, Tarragon, Wormseed, Wormwood.
Cruciferae : Mustard. Geraniaceao : Rose Geranium.
Labiatae : Balm (Melissa), Hyssop, Lavender Spike
Lavender, Marjoram, Origanum, Patchouli, Peppermint,
Rosemary, Sage, Spearmint, Thyme. LauraceaB : Bois de
Rose, Camphor, Cassia, Cinnamon, Laurel, Sassafras,
Shiu. Leguminoseae : Copaiba. Magnoliaceae ; Star
Anise. Malvaceae : Ambrette. Myristicacese : Nutmeg
and Mace. Myrtaceae : Bay Leaf, Cajuput, Clove,
Eucalyptus, Pimento. Oleaceae : Jasmine. Piperaceae ;
Cubeb and Pepper. Rosaceae : Bitter Almond, Cherry
Laurel, Rose, Wild Cherry Bark. Rutaceae : Bergamot,
Buchu, Citron, Lemon, Limes, Neroli, Orange, Petitgrain.
Santalaceae : Sandal wood. Umbelliferae : Ajowan,
Angelica, Anise, Caraway, Celery, Coriander, Cummin,
Dill, Fennel, Parsley. Verbenaceae : Verbena.
' f
CHAPTER VII
TERPENELESS AND SESQUITERPEN BLESS OILS . . .105
Preparation. Terpeneless Oils : Angelica Aniseed
Bay Bergamot Caraway Celery Cinnamon Citro-
nella Clove Coriander Geranium Ginger Hops
Lavender Lemon Lemon-grass Limes Mandarin
Orange RosemarySassafras. Sesquiterpeneless Oils.
xviii CONTENTS
SECTION III
FLORAL, FRUIT AND COMPOUNDED FLAVOURS
CHAPTER VIII
PAGE
PREPARATION OF FLORAL PERFUMES . . . .110
Extraction by Volatile Solvents Extraction by Non-
volatile Solvents Principal Flowers Carnation Cassie
Heliotrope Hyacinth Jasmine Jonquil Lily of the
Valley Rose Tuberose Violet.
CHAPTER IX
NATURAL FRUIT PRODUCTS . . . . .116
Fruit Juices Syrups Concentrated Fruit Juices Fruit
Aromas.
CHAPTER X
COMPOUNDED FLAVOURS . . . . .119
Bitters: Angostura Hamburg Hop Orange. Bouquet
Essences : Ambre Carnation Honeysuckle Jasmine
Lilac Narcissus Opoponax Stephanotis Violet.
Cake Flavours : Butter Fruit Spice. Floral
Flavours : Natural Synthetic Acacia Cassie Car-
nation Clover Cyclamen Hawthorn Hyacinth
Jasmine Lilac Lily of the Valley Moss Rose Parma
Violet Rose d'Orient Tuberose Violet White Lilac
/White Rose. Fruit Flavours : Mixtures for Strengthen-
ing Natural Fruit Flavours Apricot Banana Cherry
Peach Pear Pine-apple Raspberry Strawberry.
Herbal Beverage Extracts: Dandelion Hop Hore-
hound Sarsaparilla. Liqueur Flavours : Benedictine
Chartreuse.
CONTENTS xix
SECTION IV
ODOROUS CHEMICAL PRODUCTS
CHAPTER XI
PAGE
ALCOHOLS, PHENOLS, ALDEHYDES AND KETONES . . 127
Alcohols and Phenols : Anethol Benzyl Alcohol
Cinnamic Alcohol Citronellol Decylic Alcohol
Duodecylic Alcohol Eugenol Geraniol Iso-styrone
Linalol Menthol Nerol Nonylic Alcohol Octylic
Alcohol Phenyl-Ethyl Alcohol Phenyl-Propyl Alcohol
Safrol Santalol Terpineol Thymol Undecylic
Alcohol. Aldehydes and Ketones: Acetophenone
Anisic Aldehyde Benzaldehyde Benzylidene-Acetone
Carvone Cinnamic Aldehyde Citral Citronellal
Decylic Aldehyde Duodecylic Aldehyde Heliotropin
Heptylic Aldehyde lonone Methyl Acetophenone
Methyl - Nonyl Acetaldehyde Nonylic Aldehyde
Octylic Aldehyde Phenyl Acetaldehyde Vanillin.
CHAPTER XII
ESTERS AND UNCLASSIFIED ODOROUS BODIES . . 142
Esters : Amyl Acetate Benzyl Acetate Bornyl Acetate
Citronellyl Acetate Ethyl Acetate Ethyl-Phenyl
Acetate Geranyl Acetate Linalyl Acetate Phenyl-
Ethyl Acetate Phenyl-Propyl Acetate Terpinyl Ace-
tate Methyl Anthranilate Amyl Benzoate Benzyl
Benzoate Ethyl Benzoate Methyl Benzoate Amyl
Butyrate Benzyl Butyrate Ethyl Butyrate Geranyl
Butyrate Phenyl - Ethyl Butyrate Phenyl - Propyl
Butyrate Benzyl Cinnamate Ethyl Cinnamate Methyl
Cinnamate Benzyl Formate Citronellyl Formate
Ethyl Formate Geranyl Formate Phenyl-Ethyl For-
mate Phenyl-Propyl Formate Amyl Heptylate
xx CONTENTS
PAGR
Benzyl Propionate Citronellyl Propionate Geranyl
Propionate Phenyl-Ethyl Propionate Amyl Salicylate
Ethyl Salicylate Methyl Salicylate Ethyl Sebacate
Ethyl Succinate Amyl Valerianate Benzyl Valerianate
Bornyl Iso-Valerianate Ethyl Valerianate Geranyl
Iso- Valerianate Phenyl-Ethyl Valerianate Styrolyl
Valerianate. Other Odorous Bodies: Coumarin
Brorn-styrol Diphenyl Ether Diphenyl Methane
Indol Nerolin and Yara-yara Para-Oesol-Methyl-
Ether Skatol Synthetic Musks.
INDEX ........ 155
NOTES .... 167
LIST OF ILLUSTRATIONS
FIG. PAGE
1. Horizontal Section through the Mouth, showing Organs
of Taste ....... viii
2. View of the Lateral Wall of the Nose . . xi
3 Micrograph of Powdered Allspice. . . .2
4. Micrograph of Powdered Cinnamon . . . 7
5. Micrograph of Powdered Cloves .... 9
6. Micrograph of Powdered Ginger . . . .11
7. Micrograph of Pure Mustard Powder . . .14
8. Micrograph of Ground Pepper . . . .18
9. Micrograph of Cayenne Pepper . . . .20
10. Micrograph showing appearance of (A) Ground Cocoa-
nut Shell, (B) Ground Olive Stones, (C) Wood Dust
and (D) Cocoa Shell Powder . . . .24
11. Micrograph of Powdered Turmeric . . . 26
FLAVOURING MATERIALS
SECTION I
SPICES, CONDIMENTS AND MISCELLANEOUS
VEGETABLE AND ANIMAL FLAVOURING
BODIES
CHAPTEE I
SPICES AND CONDIMENTS
Allspice or Pimento. Allspice, Jamaica Pepper or
Pimento is the dried, unripe, full-grown berry of the
Pimento, officinalis (Myrtacese), an evergreen tree which is
indigenous to the West Indies and is especially cultivated
in Jamaica. The berries, which grow in small clusters,
are gathered and then either sun- or kiln-dried. After
drying they are either brown or grey in appearance.
Allspice is less pungent than either cloves or cassia, its
flavour being said to resemble a mixture of cloves,
cinnamon and nutmeg. It owes its flavour to a volatile
oil, largely composed of eugenol, which it contains to the
extent of 3 to 4'5 per cent, principally in its ligneous
pericarp. It finds a wide range of application, being used
in pickles, sauces, relishes, bitters, liqueurs, and as a
flavouring material in both savoury and sweet foodstuffs.
The spice appears on the market both in the whole
berries and as a fine powder. In the " whole " condition
i
FLAVOURING MATERIALS
'it' is* subject to adulteration with the berries of the Pimenta
di Tabasco (Mexican Spice) and bayberry fruit (Pimenta
acris). These berries are rather larger than and different
in appearance to the ordinary pimento berries. In the
FIG. 3. Micrograph of Powdered Allspice, showing (A) masses of
starch, (B) stone cells and (C) resin.
powder form it is most commonly adulterated with ordinary
starches, cocoanut shell, clove stems and pea flour. Other
substances which have been discovered in ground allspice
are exhausted ginger, olive stones, pear stalks (Moller,
Lehr. Pharm.), cayenne pepper and turmeric.
SPICES AND CONDIMENTS 3
Analytical Constants. The moisture content is usually
6 to 7 per cent. ; ash should not exceed 5 per cent., of
which the portion insoluble in hydrochloric acid (sand)
should not exceed 0'5 per cent., the United States standard
for ash is not more than 6 per cent.; the total ether
extract is about 10 per cent., of which about 4 per cent, is
volatile oil ; the alcoholic extract varies between 10 and
12 per cent. ; crude fibre is present to the extent of about
20 per cent., the U.S. limit being 25 per cent. ; the
quercitannic-acid content should be not less than 8 per
cent, according to U.S. standards. A quantity of starch
occurs in pimento, its presence being a distinctive feature
of the micro-examination of the spice.
Micro-examination. The main characteristics of
powdered allspice, when viewed under the microscope,
are masses of small, almost circular starch granules, large
stone cells, appearing either singly or in clusters, some-
times together with fragments of brown parenchyma, and
brown or amber-coloured pieces of gum or resin. A few
drops of oil are occasionally to be seen and short hairs of
a tapering, thick-walled nature.
Caraway. Caraway fruit, or seed as it is wrongly
termed, is the dried, ripe fruit of the Oarum carvi
(Umbelliferse), which is grown in Holland, England,
Germany, Norway and Eussia. The English variety is
of the greatest value and the Eussian of the least value,
the latter, being usually mixed with stalks and giving a
higher percentage of ash, is used chiefly as a veterinary
medicine. The agreeable, aromatic flavour of cara-
way is due to its content of 3 to 7 per cent, of a
volatile oil.
The chief adulterant of caraway fruit is exhausted
caraway ; this, however, may be detected by its shrivelled
4 FLAVOURING MATERIALS
appearance, weaker flavour, darker colour and, under the
microscope, its ruptured outer cells.
Analytical Constants. The ash is usually between 5 per
cent, and 7 5 per cent. ; according to the British Pharma-
copoeia it should not be in excess of 9 per cent., and accord-
ing to U.S. standards not over 8 per cent. The volatile-
oil content is usually 3 to 7 per cent, according to the
source of the fruit. The ether extract should be about
10 per cent.
Micro-examination. The powder shows masses of cells
of an oblong structure, from the inner epidermis. Also,
there are cells of a pitted, striated nature from the outer
epidermis, but no hairs or cell-crystals.
Cardamoms. These are the dried, fully-ripe seeds of
the Elettaria cardamomum (Scitaminacese), which grows
in the East Indies. Other varieties are used as spices, but
the B.P. recognises only the Elettaria cardamomum.
Malabar, Mangalore and Mysore cardamoms are the
chief commercial varieties. The Malabar and Mangalore
types are usually short, well-filled capsules, the Mysore
variety being larger and more loosely filled. An interest-
ing description of a very large type of cardamoms is given
by E. M. Holmes (P. & E.O.R., 1914, 302). Cardamoms
are used chiefly for culinary purposes, for sauces, curries,
cordials, etc.
The seeds should not be extracted from the pericarps
until required for use. The fruit usually yields about
75 per cent, seeds. In colour the latter are dark brown,
they contain 4 to 8 per cent, of a volatile oil and also a
quantity of fixed oil.
Analytical Constants. The B.P. requires the ash not to
exceed 6 per cent.
Micro-examination. The distinctive features of ground
SPICES AND CONDIMENTS 5
cardamoms are the deep-tinted cells of the inner covering
of the seeds, the perisperm cells containing masses of
angular starch granules and calcium oxalate crystals and
the thick-walled linear cells with oblique ends of the skin
layer. The presence of polygonal cells with straight walls
and also the content of small cells containing brown resinous
matter denote that the pericarp has been ground with
the seeds. Small spiral cells also indicate the presence of
the pericarp.
Cinnamon and Cassia. True cinnamon is the dried
bark of the Cinnamomum zelanicum (Lauracete), a
tree which is indigenous to Ceylon but is cultivated
largely in Sumatra, Java and many parts of tropical Asia.
The bark appears on the market in the form of long,
cylindrical rolls or quills, several layers usually being
found in each quill. In its preparation, the bark is first
scraped and then the inner layer is cut into slices and
dried. True cinnamon has a light yellow-brown colour
with light-coloured lines running the length of the quills.
The outer surface is marked with small round spots. The
history of the cultivation of cinnamon and cassia are
dealt with comprehensively by E. M. Holmes (P. & E.O.R.,
1916, 14 and 41).
Cinnamon has greater intrinsic value than cassia, being
of a finer and much more delicate flavour. The volatile
oil to which cinnamon owes its flavour is contained in the
bark to the extent of 0*5 to TO per cent. The oil is
composed chiefly of cinnamic aldehyde. Cinnamon is
used medicinally as a stimulant and cordial. As a
flavouring material it is used chietiy in sweet foodstuffs,
also, together with other vegetable flavouring bodies, in
the preparation of bitters, liqueurs, sauces, etc.
In the quill form cinnamon is sometimes adulteratel
6 FLAVOURING MATERIALS
with clove stems, guava bark and inferior grades of
cinnamon, the flavours of which are rather bitter.
Powdered cinnamon is adulterated with walnut-shells
(Dyer and Gilbard, Analyst, 1895, 129), starches,
turmeric, olive stones, pepper, exhausted ginger (Stock,
Analyst, 1897, 253), sand, sawdust, mustard and the
ground bark of common trees, e.g. elm.
Analytical Constants. Moisture is usually about 8 per
cent. ; ash should not be in excess of 5 per cent. (B.P.),
although genuine samples sometimes exceed this figure
slightly; volatile oil is 0*5 to 1-0 per cent. ; fixed oil, about
1-5 per cent. ; crude fibre, 30 to 35 per cent. ; alcoholic
extract, 10 to 13 per cent. Cinnamon contains very small,
oval starch granules.
The Cassia of commerce is the bark of the Cinnamomum
cassia, which is grown in India, Indo-China and China.
The quills are coarser, about four times thicker and more
loosely rolled than cinnamon quills. The outer surface
of the quills lacks the light-coloured lines noticeable on
cinnamon quills, they have oval leaf markings and small
brown excrescences.
Cassia buds are the dried flower-buds of the cassia tree.
The best qualities have a strong cinnamon flavour.
Cassia, in both quill and powder forms, is subject to
similar adulteration to cinnamon. The Chinese product
is sometimes placed on the market in a dirty condition.
It contains rather more starch than cinnamon and the
starch granules are considerably larger. Its volatile-oil
content is approximately 0*5 to 2'0 per cent.
Analytical Constants. Moisture, 8 to 12 per cent. ; ash,
5 per cent., although the United States allows up to
8 per cent., with a sand content of not more than 2 per
SPICES AND CONDIMENTS 7
cent. ; volatile oil, 0'5 to 2 per cent. ; fixed oil, 1 to 3 per
cent. ; crude fibre, about 24 per cent. ; alcoholic extract,
8 to 10 per cent. ; starch varies between the wide limits of
15 per cent, and 30 per cent.
FIG. 4. Micrograph of Powdered Cinnamon, showing (A) masses of
starch granules, (B) bast fibres and (C) stone cells.
Micro- examination. Cinnamon and cassia are very
similar when viewed under the microscope. The chief
differences are that the starch grains of cassia are larger
and present in greater numbers than in cinnamon. The
bast fibres of cinnamon are more slender, longer and
8 FLAVOURING MATERIALS
thinner-walled than those of cassia. The chief character-
istics of both cinnamon and cassia are groups of small
starch granules, somewhat resembling allspice starch but
usually with fewer granules to each group, yellow or
brown tinted cellular tissue containing occasional starch
grains, stone cells of yellow-brown shade and somewhat
oblong in shape. Cassia also contains long, yellow wood
fibres either singly or in bunches.
Gloves. -Cloves are the dried, unopened flowers of the
evergreen Eugenia caryophyllata or Caryophyllus aroma-
ticus (Myrtaceiie), which is a native of the Moluccas.
The chief cultivation areas are Amboyna, Zanzibar, Brazil,
Ceylon, Mauritius, West Indies and other tropical
regions. The flavour of cloves is due to an essential oil
which they contain to the extent of about 15 to 19 per
cent., eugenol being the chief constituent of the oil.
Cloves are used medicinally as a carminative and
stimulant; as a flavouring agent they find application
in both savoury and sweet foodstuffs, pickles, sauces,
bitters, etc.
The most usual adulterant of cloves is the exhausted
spice. This may be detected in the whole condition by
its shrivelled appearance, also its ether extract is com-
paratively small and its ash high. Clove stems are
sometimes added, but these may be detected microscopic-
ally. Clove fruit or " mother of cloves " is also added as
an adulterant ; this contains sago-like starch granules and
stone cells by which it may be distinguished. Allspice is
occasionally added as a sophistication in view of its
eugenol-content. Cereal and leguminous starches, sand,
turmeric, ground olive stones, sawdust and cocoanut
shells should be searched for as possible adulterants, but
they will rarely be found.
SPICES AND CONDIMENTS 9
Analytical Constants. Moisture varies considerably, but
is usually about 7 to 8 per cent. ; ash should not exceed
7 per cent, and sand not more than O5 per cent. (B.P.} ;
volatile oil is usually about 15 to 19 per cent. ; fixed oil,
FIG. 5. Micrograph of Powdered Cloves, showing cellular tissue
with occasional oil globules.
6 to 7 per cent. ; crude fibre, not more than 1 per cent.
(U.S. standard); alcoholic extract, 14 to 16 per cent.;
quercitannic acid, not less than 12 per cent. (U.S. standard).
Micro-examination. The characteristic appearance of
powdered cloves under the microscope is shown in Fig. 5.
io FLAVOURING MATERIALS
Masses of cellular tissue, containing brown granular
material and occasional oil globules, form the chief
objects in the field.
Coriander. Coriander is the dried, ripe fruit of the
Coriandrum sativum (Umbelliferse). In appearance the
fruit is globular, 5 mm. in diameter, yellow-brown in
colour and ribbed. It is grown chiefly in Holland,
England, Germany, Russia, Morocco, etc. A Bombay
coriander which is considerably larger than the ordinary
variety occasionally appears on the market. The aromatic
flavour of the spice is due to its content of volatile oil.
Analytical Constants. Ash is usually 5 to 6 per cent. ;
volatile ether extract should not be less than 0'5 per cent.
Micro-examination. When viewed under the micro-
scope powdered coriander shows oblique linear cells of the
endosperm, large thick- walled cells of the mesocarp and
six-sided cells of the inner vittse.
Ginger. Ginger is the dried, scraped rhizome or root-
stock of the Zingiber officinalc, a native of India and
China, which is cultivated in tropical America, Africa,
Cochin, Calicut, Australia, etc. Jamaica ginger is con-
sidered to have the finest flavour, Japan ginger the
poorest. The roots are dug from year-old plants when
the stem has withered. They are cleaned and dried in
the sun. Usually the skin is removed by scraping, the
unscraped root forming what is known in commerce as
the " coated " variety. This latter usually comes from
Africa and occasionally from Cochin and Bengal. Whole
ginger is frequently bleached with chloride of lime
solution or sulphur dioxide. The rhizome is also some-
times coated with a wash of chalk or calcium sulphate to
preserve it from the attack of insects.
Ginger owes its characteristic flavour to its content of
SPICES AND CONDIMENTS
ii
volatile oil (2 to 3 per cent.) and resinous matters. The
oleo-resin "gingerine" is obtained by percolating the
powdered spice with acetone and evaporating the extract.
Eecent work on the pungent principles of ginger is
FIG. 6. Micrograph of Powdered Ginger, showing (A) sack-shaped
starch granules, (B) bast fibres, etc.
referred to in P. & E.O.E., 1917, 64 and 102, Journ. Chem.
Soc., Trans., 1917, 769-798.
Ginger has a very wide range of uses; it is a very
favourite flavouring agent in sweet foodstuffs as well as,
together with other vegetable bodies, in pickles, sauces,
12 FLAVOURING MATERIALS
etc. The young, soft, peeled roots when preserved in sugar
syrup form a very popular conserve.
The body which is used to the greatest extent as an
adulterant of ginger, in both whole and powdered forms,
is exhausted ginger. This product is the residual material
from the manufacture of essences or tinctures of ginger by
extracting with water, dilute alcohol or strong alcohol.
Ground ginger has also been adulterated with cayenne
pepper, turmeric, starch, mineral matter and wood dust.
Analytical Constants. Moisture, 10 to 14 per cent. ; ash,
usually 3 to 4 per cent. (B.P. gives ash limit of 6 per cent.,
with not more than 1*5 per cent, of ash insoluble in water) ;
extractive matter soluble in cold distilled water should be
about 10 to 15 per cent. (B.P. gives a minimum limit of 8'5
per cent., which is decidedly low) ; extractive matter soluble
in 90 per cent, alcohol should not be less than 5 per cent.
(B.P.) ; the U.S. standards are as follows : Starch by
diastase method, not less than 42 per cent. ; crude fibre,
not more than 8 per cent. ; ash insoluble in hydrochloric
acid, not more than 3 per cent.
Micro-examination. The examination of ginger under
the microscope is not of much value in the detection of
exhausted ginger. The chief characteristics of powdered
ginger are sack-shaped starch granules, which under polar-
ised light show an unsymmetrical cross, together with bast
fibres and oleo-resin cells.
Mustard. Mustard is obtained from the seeds of the
Brassica nigra, or black mustard, and Brassica alba, or
white mustard (Journ. Chem. Soc., 1921, i. 212). The two
are powdered and mixed together to form the condiment,
most of the fixed oil being removed in the process, together
with the outer shell or husk of the black seed. The
mustard plants are native to Europe and are widely culti-
SPICES AND CONDIMENTS 13
vated in Great Britain and the United States. White
mustard seeds measure 2 to 3 mm. in diameter ; they are
pale yellow in shade and have a granular surface. The
black seeds are 1 to 1*5 mm. in diameter, dark brown in
colour and have a rough surface.
The constituents of mustard seeds are a fixed oil, a
volatile oil (0'5 to 075 per cent.) and mucilage. The
characteristic properties of mustard are due to the allyl-
iso-thiocyanate which is developed by the action of water
and an enzyme, myrosin, which is contained in both black
and white varieties, on the glucoside potassium myronate,
which is contained only in the black seeds. A glucoside,
sinalbin, occurs in the white seeds and on hydrolysis this
body forms acrinyl-iso-thiocyanate, which like allyl-iso-
thiocyanate is a very pungent oil. Mustard seeds in their
ripened state are free from starch.
The chief application of mustard is, of course, as a
condiment, but it is also used in many cases as the chief
agent in the development of piquancy in sauces, pickles,
salad creams, etc.
The adulterants which are mostly used in mustard are
mustard husk, starch, turmeric, aniline dyes, cayenne
pepper, terre alba, chalk, sand and gypsum to a lesser
extent. Charlock and rape seeds have been used in place
of true mustard. Compound or mixed mustards usually
contain wheat or other starch, which is added to reduce
the keenness of the condiment. The addition of starch is
also said to improve the keeping qualities of the mustard.
Any admixture of this type must be labelled " compound "
or " mixed " mustard. The abstraction of the fixed oil is
regarded by some authorities as an adulteration.
Analytical Standards. Moisture, 4 to 7 per cent. ; ash,
4 to 5 per cent., not over 8 per cent. (U.S. standard);
14 FLAVOURING MATERIALS
starch by diastase method, not over 2'5 per cent. ; crude
fibre, not over 5 per cent. ; volatile oil, not less than 07
per cent, (calculated as ally 1-iso-thiocy ana te).
Micro - examination. The chief characteristics of
FIG. 7. Micrograph of Pure Mustard Powder, showing (A) loose
cellular tissue and (B) seed skin.
powdered mustard under the microscope are masses of
loose, greyish cellular tissue, together with occasional
fragments of yellow seed skin.
Nutmeg and Mace. Both of these spices are derived
from the fruit of the Myristica fragrans, which is a native
SPICES AND CONDIMENTS 15
of the Malay Archipelago. The chief source of supply is
the Banda Islands. Nutmegs comprise the kernels of the
fruits, and they are covered by a fibrous arillus, which
when dried constitutes the mace of commerce.
Nutmeg. The flavouring properties of nutmeg are due
to a volatile oil (8 to 15 per cent.), besides which it con-
tains albuminous matter, starch, fixed oil and fibre. The
spice finds its chief use as a flavouring for sweet foodstuffs,
although it is used to some extent in the compounding of
bitters, etc.
Nutmegs are usually sold whole, and in this state are
not subject to much adulteration. Powdered nutmegs
have been adulterated with ground nutshells, starch, etc.
Analytical Standards. The U.S. standards for nutmeg
are as follows : Ash, not more than 5 per cent. ; sand,
not over 0*5 per cent. ; non- volatile ether extract, not less
than 25 per cent. ; crude fibre, not over 10 per cent.
Micro - examination. The chief characteristics of
powdered nutmegs are loose masses of cellular tissue
and numerous starch granules of a uniform size, nearly
circular shape and with well-marked hila.
Mace. When freshly stripped from the fruit, the
foliaceous covering which constitutes mace is bright red
in colour. After drying, however, it is yellow-brown and
brittle. The flavour of mace is due to a volatile oil,
besides which it contains a fixed oil, a carbohydrate
(amylo-dextrine) and resinous and albuminous matter.
Mace is used with other spices in sauces, pickles, etc.,
and as a flavouring material for savoury foodstuffs.
The chief sophistication of mace takes the form of the
substitution of inferior types of mace for the Banda variety.
Among these inferior types the chief are Bombay mace,
16 FLAVOURING MATERIALS
derived from the Myristica malabarica, which is useless as
a flavouring material, and Macassar mace, which although
not so flavourless as the Bombay type has a wintergreen
odour and is inferior to the Banda variety. Powdered
mace is adulterated with the above-mentioned maces and
also with ground olive stones and starches.
Analytical Standards. The U.S. standards for mace are
as follows : The fixed ether extract should not be under
20 per cent, nor over 30 per cent. ; ash, not in excess of
3 per cent. ; sand, not over 0*5 per cent. ; crude fibre, not
over 10 per cent.
Micro-examination. The main characteristics are loose-
textured masses of a greyish-white shade, very small
granules of amylo-dextrine and occasional fragments of
very light yellow-brown wood fibre.
Pepper. -Pepper is the dried, unripe berry of the
climbing shrub Piper nigrum, a native of the East Indies,
the chief varieties being derived from Siam, Penang,
Singapore, Malabar, Cochin, Allippi, Lampong, Tellicherry,
Sumatra, Mangalore, Trang, etc. Black pepper is
obtained by sun- or fire-drying the berries, whereupon
they shrivel and turn black or brown. White pepper
is produced from these dried berries by a decortication
process, which includes soaking the berries in water to
loosen the skins, drying and eliminating the skins by
friction. The principal use of pepper is as a condiment.
Many pickles and sauces contain black pepper.
The chief constituents of pepper, which impart to it
its peculiar properties, are a volatile oil (0'5 to 2 per
cent.), a pungent resin and 2 to 3 per cent, of piperin.
In the whole condition pepper is not subject to
extensive adulteration, although imitation peppercorns
made from clay are said to have been employed.
SPICES AND CONDIMENTS 17
A. Troccoli and G. Verona-Kinati (Zeits. Unters. Nahr.
Gfenussm., 1912, 736-741) found samples of peppercorns
to be adulterated with seeds of Rhamnus cartharticus
(buckthorn) and Schinus molle (American or false pepper).
The adulterants most commonly found in ground pepper
are inorganic substances, such as sand, clay, chalk,
barytes, etc., rice and other farinaceous products, ground
olive stones and nut shells, pepper shells and dust, linseed
meal, spent ginger, mustard husks, charcoal, graphite,
sawdust, turmeric, charred cocoanut shells, etc. A case in
which 10 per cent, of steatite was found has been reported.
Long pepper, which is the fruit of an Indian plant, Chavica
Roxburghii, is sometimes used as an adulterant when
price permits.
Analytical Constants. Mack Pepper. Moisture. 8 to 12
per cent. ; ash, 3 to 5 per cent., not over 7 per cent.
(U.S.); crude fibre, 10 to 11 per cent., not over 15 per
cent. (U.S.) ; starch by diastase method, not less than
25 per cent. (U.S.); non- volatile ether extract, not less
than 6 per cent. (U.S.) ; nitrogen, not less than 3'25 parts
in 100 parts of non- volatile ether extract (U.S.) ; volatile
oil, 0*5 to T8 per cent. ; piperin and resin, 7 to 8 per
cent. ; albuminoids, 7 to 12 per cent.
White Pepper. Moisture, 8 to 12 per cent. ; ash
usually 1 to 2 per cent., not more than 4 per cent. (U.S.),
with sand not more than 0'5 per cent. ; starch by
diastase method, not less than 50 per cent. (U.S.);
non-volatile ether extract, not less than 6 per cent. (U.S.) ;
nitrogen, 4 parts in 100 parts non-volatile ether extract ;
piperin and resin, 7 to 8 per cent. ; volatile oil, 0'5 to 1*8
per cent. ; albuminoids, 8 to 10 per cent.
Micro-examination. The most prominent features of
black pepper are large masses of starch and pieces of the
1 8 FLAVOURING MATERIALS
coloured parenchyma and epidermis of the shell. Yellow-
brown stone cells, with thick walls, are also fairly
numerous, as are particles of resinous matter. Needle-
shaped crystals of piperin and fragments of stem are
FIG. 8. Micrograph of Ground Pepper, showing (A) masses of starch
granules, (B) stone cells, (C) particles of shell epidermis and (D)
resinous matter.
also noticeable. Some new interesting features regarding
the micro-structure of pepper are given by T. E. Wallis
(Analyst, 1915, 190).
Red Pepper. Various species of capsica are classed
under this head. The type which is official in the B.P.
SPICES AND CONDIMENTS 19
and which is not synonymous with cayenne pepper is
called Capsicum minimum. This varies in appearance
and pungency, as do the other varieties of red pepper,
according to the country in which it is grown. For
example, the product derived from Sierra Leone is
usually yellowish-red and very pungent, that from
Zanzibar is redder and has a diminished pungency, while
the Japanese variety has a very brilliant red colour and
very much less pungency. According to the United States
definition, red pepper is the red, dried fruit of any species
of capsicum, most commercial cayenne pepper being,
however, of the C. annuum and C. fastigiatum types. A
comparison of the different varieties of red pepper is
made by L. M. Toll nan and L. C. Mitchell in Bull. 163,
U.S. Dept. of Agric., Bureau of C/iem., May 1913,
pp. 1-32.
Cayenne pepper of commerce is chiefly obtained from
Natal, Egypt, Nepaul, Zanzibar, Sierra Leone, Spain,
Hungary and Japan. Nepaul cayenne pepper is supposed
to have the finest flavour, it has a red-brown colour and
an odour resembling violets. Spanish and Hungarian
peppers, which are known respectively as "Pimiento"
and "Paprika," the latter being derived from C. tetra-
gonum, have very little pungency and give rise to the
so-called " Bird Pepper."
Cayenne pepper contains a volatile alkaloid, resin, fat,
a red colouring matter and capsaicin. The latter com-
pound is a very acrid body which is soluble in alcohol,
ether, benzene and acetic acid. The flavour of cayenne
pepper deteriorates on exposure to damp. The pepper
is used chiefly in sauces, pickles, cordials, etc., and also in
bitters.
The following are the adulterants which are alleged
20
FLAVOURING MATERIALS
to have occurred in cayenne pepper : brick dust, oxides
of iron, red lead, vermilion, gypsum, ground redwood,
coal tar dyes, turmeric, ginger, nutshells, rice starch, olive
stones, mustard hulls and exhausted capsica. The colour
FIG. 9. Micrograph of Cayenne Pepper, showing (A) Cellular Masses
containing Oil Drops and (B) Intestine-like Cells from the Epidermis
of Seed Shell.
of paprika and pimienta is occasionally deepened by
grinding with olive oil.
Analytical Constants. Moisture should not exceed 10
per cent., 5 to 7 per cent, being a fair average; ash
should not exceed 6 per cent., usually varying between 4
SPICES AND CONDIMENTS 21
per cent, and 6 per cent. ; the amount of ash insoluble in
hydrochloric acid is usually 1 to 2 per cent. ; ether
extract is usually about 18 per cent., although variations
between 17' 5 per cent, and 22 per cent, are frequently
met with ; in most cases the non- volatile ether extract
is about 90 per cent, of the total ether extract; crude
fibre should not exceed 2,8 per cent.; starch, by the
diastase method, should not exceed 1-5 per cent.
Micro-examination. The chief characteristics are
cellular masses containing occasional brilliant red oil
drops, but no starch. Cells from the epidermis are
sometimes to be observed, as are also remarkable intestine-
like cells from the skin of the seed shell.
CHAPTER II
ADULTERANTS OF SPICES AND CONDIMENTS
THE following are the approximate analytical constants
of the chief substances which are used as adulterants of
spices and condiments :
Ground Almond Shells. Ash, 2*5 to 3 per cent. ; sand,
0'05 per cent. ; volatile oil, 015 to 0*18 per cent. ; non-
volatile ether extract, 0'5 to 075 per cent. ; alcoholic
extract, 5 to 6 per cent. ; starch by diastase method, 0'5 to
1 per cent. ; crude fibre, 45 to 50 per cent.
Powdered Brazil Nut Shells. Ash, 1 '5 to 1*75 per cent. ;
sand, 01 to 0'2 per cent. ; volatile oil, O'Oo to 01 per cent. ;
non- volatile ether extract, 04 to 0'6 per cent. ; alcoholic
extract, 1-0 to 1'5 per cent.; starch by diastase method,
0*6 to 1*0 per cent. ; crude fibre about 50 per cent.
Cocoa Shell Powder. Ash, 8 to 9 per cent. ; sand, 0'5 to
1 per cent. ; volatile oil, 1 to T25 per cent. ; non- volatile
ether extract, 3 to 3'5 per cent. ; alcoholic extract, 4' 5 to
5 per cent. ; starch by diastase method, 3 to 3 -5 per cent. ;
crude fibre, 14 to 15 per cent. ; total nitrogen, 2'5 to 2*75
per cent.
Ground Cocoanut Shells. Ash, 0'5 to 0'8 per cent.;
sand, nil ; volatile oil, nil ; non-volatile ether extract, 0*2 to
04 per cent. ; alcoholic extract, 1 to To per cent. : starch
by diastase method, 0'6 to 0'9 per cent. ; crude fibre, 55 to
58 per cent.
ADULTERANTS OF SPICES & CONDIMENTS 23
Ground Walnut Shells. Ash, 1/2' to 1*5 per cent. ; sand,
trace ; volatile oil, 0*1 to 0*2 per cent. ; non- volatile ether
extract, 0'5 to 0*7 per cent. ; alcoholic extract, 1/5 to
2 per cent. ; starch by diastase method, 1 to 1/5 per cent. ;
crude fibre, 55 to 60 per cent.
Ground Buckwheat Hulls. Ash, 1/5 to 2 per cent. ;
sand, about O'Ol per cent. ; volatile oil, 0*05 to 0*08 per
cent.; non-volatile ether extract, O3 to 0*5 per cent.;
alcoholic extract, 2 to 2*5 per cent. ; starch by diastase
method, 1*25 to 1*5 per cent. ; crude fibre, 40 to 45
per cent.
Glove Stems. Ash, 7 to 8 per cent.; sand, 0'6 to 07
per cent. ; volatile oil, 4 to 5 per cent. ; non-volatile ether
extract, 3*8 to 4*1 per cent. ; alcoholic extract, 6*5 to 7 per
cent. ; starch by diastase method, 2 to 2*2 per cent. ;
crude fibre, 15 to 19 per cent.; total nitrogen, 0'92 to
- 95 per cent. ; quercitannic acid equivalent, 18 to 20
per cent.
Ground Date Stones. Ash, 1 to 1-5 per cent.; sand,
0-03 to 0*05 per cent. ; volatile oil, 0'2 to 0*5 per cent. ;
non-volatile ether extract, 8 to 8*5 per cent. ; alcoholic
extract, 16 to 17 per cent. ; starch by diastase method,
2 to 2*5 per cent. ; crude fibre, 5 to 6 per cent.
Ground Olive Stones. Ash, 0'5 to 1 per cent. ; sand,
0'25 to 0*5 per cent. ; volatile oil, 0'5 to 0*75 per cent. ;
non- volatile ether extract, 0*2 to 0*4 per cent. ; starch by
diastase method, 1'5 to 2 per cent. ; crude fibre, 50 to
60 per cent.
Pressed Linseed Meal. Ash, 5 to 6 per cent. ; sand,
0*5 to 06 per cent. ; volatile oil, 0'02 to 0'05 per cent. ;
24 FLAVOURING MATERIALS
non- volatile ether extract, 6 to 7 per cent. ; alcoholic
extract, 9 to 10 per cent. ; starch by diastase method,
13 to 15 per cent.; crude fibre, 8 to 10 per cent.; total
nitrogen, 5 to 6 per cent.
FIG. 10. Micrograph showing appearance of (A) Ground Cocoanut Shell,
(B) Ground Olive Stones, (C) Wood Dust and (D) Cocoa Shell Powder.
Oak Wood Dust. Ash, 1 to 1-5 per cent.; sand, trace;
volatile oil, 0'05 to 01 per cent.; non-volatile ether
extract, 0*5 to 1 per cent.; alcoholic extract, 6 to 7
per cent. ; starch by diastase method, 1'5 to 2 per cent. ;
crude fibre, 45 to 50 per cent. ; quercitannic acid equi-
valent, 12 to 13 per cent.
ADULTERANTS OF SPICES & CONDIMENTS 25
Red Sanderswood Dust. Ash, 0'5 to 1 per cent. ; sand,
0'5 to 0*8 per cent. ; volatile oil, TO to 1*5 per cent. ; non-
volatile ether extract, 10 to 13 per cent.; alcoholic
extract, 19 to 22 per cent. ; starch by diastase method,
I'O to 1-2 per cent. ; crude fibre, 50 to 55 per cent.
Spruce Wood Dust. Ash, 0'2 to 0*4 per cent. ; sand,
nil; volatile oil, 0*5 to 0*8 per cent.; non- volatile ether
extract, 0*6 to 1 per cent. ; alcoholic extract, 1 to 1'5
per cent. ; starch by diastase method, 1*0 to 1*2 per cent. ;
crude fibre, 60 to 65 per cent.
Pea Flour. Moisture, 15 to 16 per cent ; ash, 2*3 to 2'5
per cent. ; carbohydrates, 57 to 59 per cent. ; non-volatile
ether extract, about 2 per cent.; proteins, 22 to 23 per cent.
Bean Flour. Moisture, 11 to 12 per cent.; ash, 2 to
2-5 per cent. ; carbohydrates, 57 to 58 per cent. ; non-
volatile ether extract, 24 to 2 -5 per cent. ; proteins, 26 to
26 - 5 per cent.
Corn Flour. Moisture, 13 to 14 per cent.; ash, 1*4 to
1/5 per cent. ; carbohydrates, 64 to 65 per cent. ; non-
volatile ether extract, 6 -5 to 7 per cent. ; proteins about
10 per cent.
Wheat Flour. Moisture, 13 to 14 per cent.; ash,
0*6 to 0'7 per cent. ; carbohydrates, 71 to 72 per cent. ;
non- volatile ether extract, 1/4 to 1-6 per cent.; proteins,
13 to 13'5 per cent.
Rice Flour. Moisture, 10 to 11 per cent. ; ash, 0'5 to
0*55 per cent. ; carbohydrates, 83 to 85 per cent. ; non-
volatile ether extract, 0'8 to I'l per cent.; proteins, 5 to
5 '5 per cent.
Turmeric. This substance is important both as an
adulterant and as a condiment. In the latter quality it
is used extensively in curry powder.
26
FLAVOURING MATERIALS
Turmeric, Curcuma longa, is a member of the same
species of plants as ginger. It is indigenous to Cochin
China and the East Indies. Its chief constituent is the
yellow colouring matter "curcumin," besides which it
FIG. 11. Micrograph of Powdered Turmeric, showing (A) Starch
Granules and (B) Cellular Tissue containing Yellow Resin.
contains a volatile oil, gum, starch and cellulose. Cur-
cumin is insoluble in cold water, but soluble in alcohol
and ether. Turmeric is used as an adulterant, particularly
in mustard and ginger, to cover, by means of its yellow
colour, admixtures with starches.
ADULTERANTS OF SPICES & CONDIMENTS 27
Analytical Constants. Moisture, 8 to 10 per cent. ; ash,
6 to 9 per cent. ; total ether extract, 10 to 12 per cent. ;
volatile ether extract, 2 to 5 per cent. ; alcoholic extract,
6 to 10 per cent.; crude fibre, 4 to 6 per cent. ; starch by
diastase method, 30 to 40 per cent.
Micro-examination. The chief characteristics of
powdered turmeric when examined under the microscope
are the yellow masses of distinctly marked starch granules,
cellular tissue and occasional fragments of intense yellow
resin.
CHAPTEE III
ANALYTICAL METHODS
THE following are the most commonly used general
chemical methods for the analysis of spices and condi-
ments. Particular methods relating to special articles
are dealt with later.
Moisture. 2 to 3 gms. of the spice are dried to constant
weight in an air oven at 110 C. The loss in weight
represents moisture and volatile oil, the latter being
deducted after determination from the ether extract.
Ash. 2 to 3 gms. are incinerated in the usual manner
in a platinum crucible and the ash weighed. The amount
of ash soluble in water is estimated by treating the ash
with 50 to 100 c.c. of boiling water, filtering on to a tared
filter paper or Gooch crucible, drying and weighing. The
amount of ash soluble in hydrochloric acid (sand) is
estimated by boiling the ash with 40 to 50 c.c. of 10 per
cent, hydrochloric acid, filtering on to a tared Gooch
crucible, washing with hot water, drying and weighing.
Inorganic bodies used as adulterants are estimated in the
ash by the usual methods of quantitative analysis.
Ether Extract. 2 to 3 gms. of the dried powder from
the moisture estimation are extracted with pure, dry
ether in the Soxhlet apparatus. The ether is evaporated
and the extract desiccated over sulphuric acid for a day.
The extract is weighed for the total ether extract figure.
28
ANALYTICAL METHODS 29
The container is then heated very gradually to 110 C. in
an air oven and the heating continued until the weight
is constant. The residue gives the non-volatile ether
extract figure and the loss in weight the volatile oil
figure.
Volatile oil is also estimated by distilling a mixture of
the spice and water, the distillate being collected in a
graduated cylinder, in which the amount of volatile oil
can be read off. In cases where the volatile oil is slightly
soluble in water special treatment is required. The water
and volatile oil are separated and the aqueous portion
extracted with petroleum ether. The extract is evaporated
at a low temperature in a tared vessel and the amount of
oil remaining added to the volume of oil read off in the
cylinder.
Alcoholic Extract. 2 to 3 gms. of the spice are shaken
occasionally for a day with 100 c.c. of 95 per cent, alcohol,
the solution allowed to stand overnight and then filtered.
A measured quantity of the filtrate is evaporated to dry-
ness on a water bath and heated to constant weight
at 110C.
Starch. A preliminary extraction is usually performed,
except in the case of cassia and cinnamon, with ether and
alcohol on 4 to 5 gms. of the spice. The residue is then
transferred to a flask and the starch estimated by the
diastase method or the acid conversion method. The
diastase method is specially suitable for spices or condi-
ments which contain only small quantities of starch.
Crude Fibre. 2 to 3 gms. of the spice are extracted
with ether and then boiled successively with dilute
sulphuric acid and dilute caustic potash. The liquor is
diluted and centrifuged, the final residue being dried to
constant weight at 110 C. in an air oven.
30 FLAVOURING MATERIALS
Nitrogen. The Kjeldahl method is usually employed
except in special cases.
Micro-examination. The following methods of clearing
dense tissues are sometimes used in the preparation of
spices for examination under the microscope : (1) Stand-
ing in chloral hydrate solution for a day. (2) Successive
treatment with boiling dilute acid and alkali. (3) A drop
or two of weak alkali added to the water-mount of the
substance.
A drop of a solution of iodine in potassium iodide
introduced under the cover-glass is useful in distinguish-
ing starch granules and amylo-dextrine. Starch granules
turn black with iodine, amylo-dextrine granules, red.
SPECIAL METHODS
Cloves. The Tannin Equivalent, Oxygen Absorbed
Figure, or Quercitannic Acid Content of cloves is estimated
by first extracting the spice with ether and then finding
the oxidising power of potassium permanganate on an
aqueous extract of the residue, proceeding in a similar
manner as in the Lowenthal tannin estimation. 10 c.c.
N
^ oxalic acid are equivalent to 0'0623 gms. quercitannic
acid or 0008 gms. oxygen absorbed.
Ginger. Sophistication with cayenne pepper may be
detected by boiling a small quantity of the sample with
alcohol, filtering the extract and evaporating to dryness.
The pungent taste of cayenne is at once apparent in the
extract if the sample is adulterated with this substance.
Dyer and Gilbard (Analyst, 1893, 199) indicate the
value of the alcoholic extract and water-soluble ash in
detecting adulteration with exhausted ginger. In the
analysis of pure ginger the alcoholic extract averaged
ANALYTICAL METHODS 31
2*8 per cent., while exhausted ginger gave only 1*2 per
cent. The water-soluble ash was 27 per cent, with pure
ginger and O35 per cent, in the case of exhausted ginger.
Stock, in the Analyst, 1894, 312, makes some interesting
remarks on the grinding of ginger roots for analytical
purposes.
Mace. Several chemical tests are in existence for the
detection of the presence of Bombay mace in the Banda
or true variety. When basic lead acetate is added to the
alcoholic extract a red precipitate is obtained if Bombay
mace is present ; true mace gives a white precipitate.
Although the petroleum ether extracts of Bombay and
true mace are similar, Southall Brothers and Barclay have
demonstrated that a subsequent extraction with ether
gives 35 per cent, from Bombay mace compared with
1*7 per cent, from true mace. Solstein (Zeits. OffentL Chem.,
3, 253) recommends a similar process for detection and
estimation of Bombay mace. Further chemical tests are
given by Schneider, Journ. PharmacoL, 4, 57 ; Hefelmann,
Pharm. Zeit., 1891, 122; Busse, Zeits. Untcrs. Nahr.
Genussm., 1904, 590 ; Cripps, Analyst, 1909, 519.
Macassar mace may be tested for by Griebel's method
(Zeits. Unters. Nahr. Genussm., 1909, 202) as follows : A
small quantity is shaken with light petroleum, filtered
and mixed with 2 c.c. glacial acetic acid. Concentrated
sulphuric acid is carefully poured down the side of the
tube to form a layer under the acetic acid solution, a red
ring forming at the junction of the two solutions when
Macassar mace is present in excess of 20 per cent.
Mustard. D. Kaquet (Ann. Chim. Anal., 1912, 174-
178) suggests the use of dilute alcohol in place of water
in the distillation method of estimating essential oil in
mustard as giving more concordant results. The following
32 FLAVOURING MATERIALS
percentages of mustard oil (as ailyl-thiocarbimide) were
found in samples of black mustard of different origin :
English, 1*39 per cent. ; Greek, 1-2 per cent. ; French, T08
per cent. ; Sicilian, 0'99 per cent. ; Italian, O99 per cent. ;
Bombay, 0*81 per cent.
A note on the Iodine Values of mustard oils is given
in the Analyst, 1918, 216.
Cayenne pepper is detected in a similar manner to
that mentioned above under ginger.
When turmeric is present in mustard the addition of
ammonia produces an orange-red colour. Bohrisch, in the
Analyst, 1904, 29, 372, gives an alcoholic extraction
method for the detection of turmeric and aniline dyes in
mustard. E. Sievers (Zeits. Unters. Nahr. Genussm., 1912,
393) proposes a modification of Bohrisch's process for
turmeric as follows : A few gms. of mustard are moistened
with alcohol and 10 c.c. of ether added. The mixture is
shaken, allowed to settle, the ethereal layer poured on to
a strip of filter paper and tested for turmeric in the usual
manner with boric acid.
Kreis (Chem. Zett., 1910, 34, 1021) has devised a method
for the estimation of starch in mustard in which the
starch is weighed directly.
Pepper. Many chemical methods have been suggested
for the detection of olive stones or " poivrette " in pepper,
most of these depending on colour reactions.
Chevreau makes use of aniline acetate, which colours
olive stones yellowish- brown and leaves the pepper greyish
or white.
D. Martelli (Analyst, 1895, 181) uses phloroglucinol in
hydrochloric acid, which when heated with olive stones
imparts to them a brilliant red colour.
Jumeau employs a solution of iodine in equal parts of
ANALYTICAL METHODS 33
alcohol and ether. This gives a deep brown colour with
pepper and yellow with olive stones.
Neuss treats the sample with hydrochloric acid, pepper
being turned yellow, while most adulterants remain
unchanged.
A method devised by A. W. Stokes (Analyst, 1889, 82)
for the microscopic detection of poivrette and long pepper
is as follows : A sample is warmed with ammonia, then
washed with water and examined under the microscope
in glycerine, using polarised light. With pepper it is
possible to obtain an entirely dark field by rotating the
prisms, this being impossible with poivrette, long pepper
or rice.
CHAPTEK IV
MISCELLANEOUS FLAVOUBING MATEEIALS
VEGETABLE BODIES
Agaric. This is a white, spongy fungus, Polyporus
officinalis, which grows on old larch trees in Eastern
Europe and Siberia. Its chief constituent is agaracin
(agaricic acid), a white crystalline powder which melts at
138 C., is insoluble in water, but soluble 1 : 140 in 90 per
cent, alcohol. It possesses an astringent taste, but no
characteristic odour, its chief usage as a flavouring agent
being in beverages of a bitter nature.
Aloes. These are derived from Aloe chinensis, A. vera
and A. Perryi, known commercially as Socotrine,
Zanzibar, or Curacao aloes. Cape aloes are not official
and are used chiefly for veterinary purposes. Aloes
occur in hard, brown masses, having a dull fracture.
The chief supplies are obtained from the West Indies.
They possess a characteristic, disagreeable odour and a
bitter taste, being used chiefly in bitters. The chief
constituents of aloes are aloin, emodin or trioxymethylan-
thraquinone, a small amount of gallic acid, resin and a
trace (Q'0003 per cent.) of volatile oil. Tests : Ash, not
over 5 per cent. ; moisture, not over 10 per cent. ; 1 gm. of
aloes warmed with 5 c.c. of 95 per cent, alcohol should
give after cooling an almost clear solution. For tests for
34
MISCELLANEOUS FLAVOURING MATERIALS 35
adulterants see Allen's Commercial Organic Analysis, 1913,
vol. vii. 138, 146. Aloin tests are contained in the Pharm.
Journ., ii./10, 235.
Angelica Hoot and Seed. The two main types are the
European variety Angelica archangelica, and the
American variety Angelica atropurpurea. The roots
have the characteristic, aromatic angelica taste, the
American being lighter coloured and less aromatic. The
fruits or seeds are oblong, J" x -J", round at the ends and
whitish in appearance. Archangelica contains 0'3 to 1*0
per cent, of an essential oil. Angelica has a large variety
of uses as a flavouring agent ; it is used in bitters and in
liqueurs of the Vermouth, Chartreuse, Benedictine, Carrnel
Monks, etc., types.
Angostura Bark or Cusparia Bark. This is the dried
bark of Cusparia febrifuga. It occurs on the market in
slightly curved and quilled pieces about |" in thickness.
It is yellowish in outer appearance, has a bitter flavour
and is used as a bitter tonic and stimulant. Its properties
are due to the alkaloids cusparine, cusparidine, galipin
and galipoidine. In the U.S.D. Arch. d. Pharm., 1911, 174,
the account of an examination is given which revealed a
content of cusparine, cuspareine and galipoidine (see also
Journ. Chem. Soc., 1921, i. 121).
Anise and Star Anise. Anise is the dried ripe fruit of
Pimpinella anisum. It is obtained chiefly from Spain,
Italy, Kussia, Malta and Germany. It has a sweet taste
and characteristic odour, its chief use being as a stomachic,
carminative and aromatic flavouring agent for many
purposes. The flavour of anise is due to its content of an
essential oil (1-5 to 6'0 per cent.). The fruits should be
free from sand and earthy matter. Conium has occasionally
been detected as an adulterant, its presence being revealed
36 FLAVOURING MATERIALS
by the evolution of a mousy odour when the anise is
ground with potash.
Star anise is the fruit of Illicium verum, which is
obtained chiefly from China. It has a characteristic
aromatic taste due to its content of volatile oil. Aniseed
oil of commerce is, in fact, produced almost wholly from
Illicium verum. I. religiosum, originating from Japan, is
occasionally used as an adulterant. It has a flavour
resembling turpentine. Anise and Star anise are used in
liqueurs of the type of Anisette de Hollande, Anisette de
Bordeaux, Absinthe, etc., also in cake-flavouring essences,
bitter beverages, flavours of the " cough " type, etc.
Arnica. This is derived from Arnica montana and
consists of the dried flower-heads of the plant. Previous
to 1914 the root was official in the B.P. It is obtained
from the mountainous regions of Central and Southern
Europe. Its taste is acrid and bitter, resembling apple to
some extent, and its use is chiefly as a stomachic and
weak stimulant. It contains a volatile oil to the extent
of 0'5 to TO per cent. Occasional adulteration occurs
with the flowers of Inula Britannica.
Balm. -This is the fresh herb Melissa officinalis, which
is grown in Mediterranean countries. It is used as a
digestive, having been introduced by the Carmelite monks
of Paris in 1611, in the form of Eau de Melisse des
Carmes. A note on the historical interest of balm
appears in the Chem. & Drug., ii./09, 819. It has a flavour
resembling lemon. The essential-oil content of balm is
0'014 to 0104 per cent. It is used in bitter beverages, etc.
Buctibean. This is the leaves of Menyanthes trifoliata, of
the gentian species. It has a very bitter flavour, but no
odour, being used chiefly as a bitter tonic and carthartic,
in some cases along with wormwood and gentian.
MISCELLANEOUS FLAVOURING MATERIALS 37
Burdock. This is the herb Arctium lappa, the whole
herb, root and fruits being used. It has a sweet, muci-
laginous taste and is used along with bitters in herbal
beverages. The rhizome contains about 0'17 per cent,
and the leaves 0*28 per cent, of essential oil.
Calamus or Sweet Flag. This is the rhizome of Acorus
calamus, grown in China, Japan and Russia. The roots
are pale yellowish-brown in colour and have a bitter,
aromatic flavour. The peeled root, which often appears
on the market in a split condition, is less aromatic. It
contains 0'8 to 3'5 per cent, of volatile oil. It is used in
the compounding of bitters.
Calisaya. This is a non-official cinchona bark derived
from Cinchona calisaya or Yellow Cinchona. The bark,
which is sold in quilled pieces, has a bitter flavour and
slight odour. It is employed in the preparation of bitter
beverages.
Carobcu. This consists of the leaves of Jacaranda
lancifoliata. The leaves have a bitter taste, somewhat
resembling tea, but no odour. According to the Brit. Med.
Journ., i./85, 327, they contain aromatic resin, but no
alkaloid.
Cascarilla. This is the dried bark of Croton elutaria,
grown in the Bahamas, which occurs on the market in
the form of short quills of about J" in diameter, having a
chalky surface. The chief constituents are 1*5 to 3 per
cent, of a volatile oil, tannin, resins, and also the bitter,
crystalline substance cascarillin. The latter substance is
most easily extracted by means of acetone. It is used
like columba and gentian as an aromatic tonic possessing
a bitter aromatic flavour. Tests: Ash is usually about
8 per cent. The B.P. ash-limit is 11 per cent.
Celery Seeds. These are the seeds of Apium graveolens,
38 FLAVOURING MATERIALS
cultivated in European countries. They are used chiefly
as a culinary flavour, also in pickles, etc., and for their
tonic properties combined with such drugs as damiana,
coca and kola. They contain 2'3 to 5 per cent, of a
volatile oil.
Gentaury. This comprises the whole herb Erythrcea
centaurium. It has a bitter flavour and a slight odour,
which, however, disappears on drying the herb. It is used
in bitters.
Chiretta. This comprises the entire plant Swertia
chirata, which is collected when in flower and dried.
It is derived from Northern India, where it is exten-
sively used as a bitter. It resembles in properties
gentian, columba, etc. The active principles are chiratin,
a bitter substance, and ophelic acid. No tannin is
present. It is used as a bitter principle in beer.
Colocynth. This is the dried pulp of Citrullus colo-
cynthis, or bitter apple, free from seeds. The pulp is
yellowish white, spongy and very bitter. It is obtained
from Smyrna, Trieste, France, Spain, Egypt, Cyprus and
Persia. Its chief constituents are a glucoside, colocynthin,
and resinous matter. It is used in very small quantities
in bitters. Tests : Ash, not less than 9 per cent. ; aqueous
extract should not give blue colour with iodine. The B.P.
requires not more than 2 per cent, of fixed oil.
Columba. This consists of the dried root of Jateorhiza
columba or J. palmata cut into transverse slices. It is
obtained from East African forests and has a bitter taste
and musty odour. The chief constituents of columba root
are a white crystalline substance columbin, an alkaloid
berberine, columbic acid and starch. It contains O005
per cent, of an essential oil. It is used as a bitter principle
in beverages.
MISCELLANEOUS FLAVOURING MATERIALS 39
Cubebs. This is the dried, full-grown, unripe fruit of
Piper cubeba, which resembles black pepper in many
respects. It occurs on the market as dried berries,
usually with the stalks attached. Java, Sumatra and
Borneo are the chief sources of supply. It has a
pleasant, aromatic odour, a rather bitter, pungent taste,
and should be free from a mace-like flavour. Eastern
peoples use cubebs as a condiment; it has, however,
many applications both as a flavouring material in bitter
beverages and as a stimulant and stomachic medicine.
Its chief constituents are 8 to 18 per cent, of a volatile
oil, about 20 per cent, of an oleo-resin (Chem. & Drug.,
ii./09, 579), cubebic acid, cubebin, and a small amount of
piperin. It is sometimes adulterated with similar shaped
fruits of the Rhamnus and Piper species (Chem. & Drug,,
ii./05, 797). Tests : Ash, not over 8 per cent. (B.P. limit) ;
the ether extract should be about 20 per cent.
Dandelion. This consists of the smooth, yellowish-
brown root of Taraxacum officinale, collected in the
autumn. It is a bitter like columba. Its chief con-
stituents are taraxacin, asparagin, resins, salts, inulin
and mannite. The dried roots are liable to attacks from
insects, and should not be kept for more than a year ; the
juice of the root, also, undergoes alteration on exposure
to air. Dandelion is a bitter tonic used in beverages,
bitters, etc. It is also roasted, ground and used in place
of coffee or as a dandelion coffee. Dandelion root
resembles pellitory root, but has not its bitterness.
Elder Floiuers. These are the dried flowers of the
European plant Sambucus nigra, separated from the
stalks. The flowers blacken quickly if left in the un-
dried condition. They contain about 0'037 per cent, of
a volatile oil and are used as a household remedy for
40 FLAVOURING MATERIALS
catarrh. Their taste is mucilaginous, and their odour
slight, but characteristic. Elder bark is also used as a
bitter principle to some extent ; its taste is sweet at first,
then bitter.
Elecampane Root. This is derived from Inula helenium,
which is grown in European countries. The root resembles
belladonna in shape and appearance, but on scraping does
not show white as does belladonna. The flavour is bitter
and aromatic, the odour resembling camphor and orris
root. Its chief constituents are inulin and helenin. It is
used in the compounding of bitters.
Fennel. This is the greenish-brown, dried, ripe fruit of
Fceniculum vulgar c, which is grown in Southern Europe.
The fruit has a sweet aromatic flavour resembling anise,
which, however, varies slightly according to derivation.
Fennel is obtained from France and Germany and also
India, Persia and Japan. Its chief constituent is its
volatile oil, which it contains to the extent of 4 to 6 per
cent. It is sometimes adulterated with the exhausted
fruit. Its chief usage as a flavouring agent is in liqueurs
of the anisette type, bitters, etc. Tests : Ash should not
exceed 11 per cent., usually being between 8 per cent, and
10 per cent.
G-alanga. This is the dark red root of Alpinia officinarnm
and the A. galanga, which is obtained chiefly from the
East Indies. Its flavour is spicy and pungent, resembling
ginger. It is used in bitters of the angostura type and in
liqueurs, such as vermouth.
Garlic. This is the bulb of Allium sativum, which is
grown in Spain, Portugal and Italy. It has the well-
known flavour of onions, but much intensified. The
essential-oil content of garlic is O'OOS to 0*01 per cent.
It is used in culinary dishes, pickles, etc.
MISCELLANEOUS FLAVOURING MATERIALS 41
Gentian. This comprises the dried rhizome of Gentiana
lutea, the exterior of which is yellowish-brown, the interior
being of an orange tint. It is obtained from the moun-
tainous regions of Central and Southern Europe. Its
flavour is sweet at first, then exceedingly bitter. The
chief constituents are a very bitter glucoside gentio-
picrin, gentianic acid, a sugar gentianose and a trace of
volatile oil. Gentian has occasionally been adulterated
with the root of the Rumex alpinus, and in the powdered
state with ground olive stones. It is used as a bitter
principle in beer and herbal beverages. Tests : Ash, not
over 6 per cent. (B. P. limit) ; not less than 33 per cent, of
the ash must be soluble in water ; the aqueous extract of
gentian should total 30 to 40 per cent. ; for further tests
see the B.P.
Ginseng. This name is applied to the roots of several
Asiatic plants, and also to Panax quinguifolium or False
Ginseng. The Chinese ascribe to it extraordinary medi-
cinal properties. It has a sweet, slightly aromatic taste
and demulcent properties. The Pharm. Journ.,i(./lQ, 575,
gives an account of its culture in Kentucky and its
conveyance to China (see also Journ. Chem. Soc., 1921,
i. 296).
Guaiac Wood. This comprises the heartwood of
Guaiacum ojfficinale or G. sanctum, which is of a dark,
greenish-brown colour and heavier than water. It is
grown chiefly in Jamaica and San Domingo, the wood
being marketed in the form of shavings or raspings. It
has an aromatic, biting taste and is used in certain bitter
beverages. Its constituents are 26 per cent, of resin,
containing guaiacic, guaiaconic and guaiacinic acids, also
two saponins, a neutral guaiac-saponin and guaiacsaponic
acid. The wood and resin have stimulating and diaphoretic
42 FLAVOURING MATERIALS
properties. Tests: Ash, 1 to 2 per cent.; the alcoholic
extract of the wood gives a blue coloration with dilute
ferric chloride.
Holy Thistle. This is the herb Carbenia benedicta. Its
flavour is extremely bitter, but it possesses no distinctive
odour.
Hops. These are the flowers of Humulus lupulus, which
are usually treated with sulphurous acid to prevent them
going brown and developing an odour of valerian. The
flavour of hops is bitter and aromatic ; they are used
chiefly as a flavouring agent in beverages. The bitter
principles are in greatest predominance in the yellow
glands of the axil of the fruit, and these, when separated
by sifting, form the substance lupulin. Tests : Ash, 5 to
7 per cent.; ethereal extract, 9 to 15 per cent.; when
distilled with water, should yield 0*9 per cent, volatile oil ;
the benzol extract is a good criterion of the quality of
hops, usually varying from 12 to 19 per cent.
Horehound. This is the herb Marrubium vulgare, which
is used largely in the preparation of herbal beverages.
It has a pleasant, aromatic, bitter taste and characteristic
odour, also it possesses tonic properties.
Hyssop. This is the herb Hyssopus officinctlis, which is
grown in European countries. It has an aromatic, bitter
flavour and camphoraceous odour. Its essential - oil
content is 0*3 to O9 per cent. The herb is used in the
compounding of liqueurs of the Chartreuse, Benedictine,
Carmel Monks, etc. types.
Juniper Berries. These are the ripe fruits of the
European plant Juniperus communis. They are nearly
black in colour, with a greyish bloom. The flavour is
characteristic, being of an aromatic, turpentine nature.
The chief constituent is an essential oil (0*5 to 1*5 per
MISCELLANEOUS FLAVOURING MATERIALS 43
cent.), composed mainly of terpenes. It is used in
beverages.
Kola. This is the dried fleshy seeds of Cola vera,
obtained from West Africa and the West Indies. The
seeds contain TO to 2 -5 per cent, of caffeine and also a
glucoside, kolanin. They have an astringent flavour and
are used in the manufacture of certain beverages. See
also Brit. Med. Journ., i./90, 969, and Chem. & Drug.,
ii./09, 580.
Laurel. Both the leaves and the fruits of the laurel,
Laurus nobilis, are used. This laurel is grown chiefly in
Europe, Syria and Asia Minor, The flavour is aromatic,
its chief constituent being about 1 per cent, essential oil.
The fruits contain about 30 per cent, of a fixed oil.
Lavender Flowers. These are the flowers of Lavandula
vera separated from the spikes. They are grown in
England, France, Spain and Italy. Their characteristic
lavender flavour is due to an essential oil which they
contain to the extent of O5 to TO per cent.
Liquorice. This is the root of Glycyrrhiza glabra,
obtained from Spain, Eussia, Italy, Persia, Arabia, etc.,
and also grown to some extent in England. The root has
varying degrees of acridity according to its source. It
owes its characteristic flavour to the active principle
glycyrrhizin, which occurs in the root in combination
with ammonia. Other constituents are resin, starch, gum,
grape sugar, asparagin and malic acid. Aqueous extrac-
tion of the root usually gives 24 to 38 per cent, solid
extract. The following references deal with the analysis
of liquorice root and extract : Chem. & Drug., ii./09, 580,
i./lO, 21, i./ll, 133 ; Pharm. Journ., i./06, 494, i./13, 365,
370; Am. Journ. Pharm., Dec. 1912; see also B.P. and
U.S.P. for extraction tests. Ash, 3 to 4 per cent., not
44 FLAVOURING MATERIALS
over 6 per cent. (B.P.). Liquorice has a very widespread
use as a flavouring material ; it is also used in beverages
to produce a froth heading.
Lovage. This is the grey-brown root of Levisticum
qfficinale. It has a very thick, white spongy bark. Its
flavour is slightly bitter, resembling fenugreek. It
contains 0*3 to TO per cent, of a volatile oil.
Manna. This is the pale, yellow, concrete saccharine
exudation from Fraxinus ornus and F. rotundifolia. It
has a sweet flavour similar to honey and consists mainly
(70 to 80 per cent.) of mannite, sugar, extractive matter
and 10 per cent, moisture. Mannite is not fermented by
yeast, also it does not reduce Fehling's solution.
Marjoram. This is derived from the herb Origanum
majorana, which is grown in European countries. It is
used chiefly as a culinary flavour, being agreeably aromatic
in taste. It contains 07 to 0'9 per cent, of a volatile oil.
Musk Seeds. These are the greyish-brown seeds of
Hibiscus abelmoschus, which is grown in the East and
West Indies and Java. They are used as a coffee flavour
and in the East as an adulterant for musk. Their flavour
is greasy and distinctly of a musk type. They contain
about 0*2 per cent, volatile oil.
Orris Eoot. This is the root of Iris florentina. It has
a fine, violet odour, being used in many flavouring
essences and in liqueurs of the anisette type. The best
quality of orris root is Florentine. It contains " butter
of orris," a sweet, violet-scented fatty material, to the
extent of 0*10 to 0'20 per cent.
Paradise Grains. These are the seeds of Amomum
melegueta, which is grown in West Africa. They are
used in bitters and contain 0*3 to 07 per cent, of a
volatile oil.
MISCELLANEOUS FLAVOURING MATERIALS 45
Pellitory Root. This is the dried, brown root of
Anacydus Pyrethrum, derived from Morocco and Algeria.
It has a pungent, acrid taste, a characteristic odour, and
is used as a salivatory stimulant in bitters, etc. Its chief
constituents are a volatile oil, resins and inulin. It has
been adulterated with the root of the Corrigiola telephii-
folia, which is similar in size and is obtained from Morocco.
Peppermint. This is the herb Mentha piperita, which
is grown in America, England, France, etc. Its chief
constituent is a volatile oil rich in menthol and menthyl
esters, which is distilled from the fresh, flowering herb.
The flavour is aromatic, with cold pungency. It has a
widespread usage in many types of flavours.
Polypody. This consists of the root and leaves of
Polypodium vulgare. The root is slender and dark brown
in appearance, its taste is slightly acrid and sweet, but it
is devoid of odour.
Pomegranate. This is the dried root and root-bark of
Punica granatum. It has an astringent flavour, but no
odour. Its chief constituents are 0'5 to 0'7 per cent., and
even as high as 1 per cent, of alkaloids, composed chiefly
of pelletierine, etc., and 20 per cent, of tannin. It is used
to some extent in the compounding of bitters. Tests:
Ash, 5 to 13 per cent., not over 15 per cent. See Squire's
Comp. to B.P., p. 671, for summary of further tests.
Prickly Ash Berries and Bark. These are the fruit and
bark of Xanthoxylum americanum, or Toothache Tree.
They have a very pungent, bitter taste and cause a flow
of saliva. They are used in herbal beverages.
Pyrethrum Root. See Pellitory Root.
Quassia. This is the wood of Picrcena excelsa, obtained
from Jamaica. The wood is sold in yellowish-white chips
or raspings, it has a very bitter taste, resembling, but
46 FLAVOURING MATERIALS
much more bitter than, sassafras and- columba. It is
used as a bitter principle in beer. Its chief constituents
are the bitter principle " quassin " and an essential oil.
Quassia is sometimes adulterated with the exhausted
wood. Tests : Ash about 3 per cent., not over 4 per cent.
Red Peruvian Bark. This is the bark of Cinchona
succirulra, which is usually sold in quilled pieces. It is
bitter and astringent in flavour and has a slight odour
due to its containing a small quantity of essential oil.
Its chief constituents are quinine, quinidine, cinchonine
and cinchonidine. Good red bark should yield 5 to 6
per cent, of alkaloids, not less than half of which should
be quinine and cinchonidine. It is used in bitter
beverages of a tonic character. Tests : Ash, 2 to 4 per
cent. ; for alkaloid-strength tests see B.P., U.S.P., etc.
Assay methods are also given in Pharm. Journ., ii./Oo,
579, and Chem & Drug., i./08, 21. The alpha-naphthol
test for cinchona alkaloids is described in Am. Journ.
Pharm., 1913, 502 ; Pharm. Journ., ii./13, 881 ; and Chem.
& Drug., i./14, 84.
Rhubarl. This is the root of Rheum palmatum, R.
officinale and other species. It is obtained from China,
Turkey and the East Indies. It has a nauseous,
astringent taste and is used as a flavouring matter in
bitters. Notes on the constituents of rhubarb are to be
found in Journ. Chem. Soc., Trans., 1911, 946; Pharm.
Journ., i./13, 403. Tests: Ash, 7 to 12 per cent.,
although Chattaway and Moor (Analyst, 1903, 207)
found nearly 30 per cent. The B.P. ash limit is 15 per
cent. A colorimetric method for the assay of rhubarb is
given in Pharm. Journ., ii./05, 580.
Roman Chamomile. These are the buff, dried, expanded
flower-heads of Anthemis nobilis, which is grown in
MISCELLANEOUS FLAVOURING MATERIALS 47
Europe and America. The flavour is bitter and aromatic,
the flowers being used in the preparation of herbal
beverages. They contain 0*8 to TO per cent, of volatile
oil. The constituents of the flowers are given in Journ.
Chem. Soc., Trans., 1914, 1844. Tests: The ash should
not exceed 5 per cent.
Rosemary. This is the herb Eosmarinus officinalis,
which is grown in Spain, France and Italy. It has an
aromatic taste and characteristic odour, due to its content
of 1 to 2 per cent, of a volatile oil. It is used in many
flavouring essences, also in the compounding of bitters,
etc.
Sage. This is the herb Salvia officinalis, which is
grown in European countries. It is used chiefly as a
culinary flavour. Its content of volatile oil amounts to
1*3 to 2'5 per cent.
Sarsaparilla. This is the brown root of Smilax ornata.
Several varieties are to be found on the market, e.g.
Guayaquil, Mexican, Honduras, Ked Jamaica, Orange or
Native Jamaica, Lima, etc. The root has long been used
as a tonic and blood purifier, particularly in the form of
bitter beverages. The flavour is slightly acrid. It con-
tains a saponin glucoside, sarsasaponin, and a phytosterolin
(Journ. Chem. Soc., Trans., 1914, 219). Tests : Ash, 5 to 7
per cent.
Sassafras. This comprises the dried root of Sassafras
officinale or S. variifolium, which is grown in North
America. The root bark has a rust-brown colour, is
aromatic, sweet and slightly astringent in flavour. The
whole root is sold in the form of chips. The flavour is
due to the presence of 3 to 9 per cent, of a volatile oil,
which is usually distilled from the root bark. Sassafras
is used as a flavouring material for herbal beverages and
48 FLAVOURING MATERIALS
in the compounding of liqueurs of the anisette type.
Tests : Ash, about 2 per cent.
Saxifrage. This is the herb Pimpinella saxifrage. It
is cucumber-like in flavour, but has not much odour.
It is used in the preparation of bitter beverages.
Senega. This is the dried yellowish-grey root of
Polygala senega, which is obtained from North America.
It has an acrid, slightly acid flavour, resembling methyl
salicylate, and a rather rancid odour. Its chief constitu-
ents are senegin, a glucoside of a saponin nature, and
polygalic acid ; the volatile-oil content of the root is
0*25 to 0*33 per cent. Tests : Ash, 2 to 5 per cent. ;
when extracted with ether, acidified with hydrochloric
acid, water added and the ether evaporated off, the
aqueous solution should give a violet-red colour with a
drop of dilute ferric chloride solution. The following
roots have some resemblance in appearance to senega :
Valerian, arnica, serpentary and green hellebore.
Senna. This consists of the leaves and pods of Cassia
angustifolia (Tinnevelly or East Indian Senna) and
C. acutifolia (Alexandrian Senna). The latter are usually
preferred as being milder flavoured ; the taste is sickly
sweet, with a resemblance to tea. Senna is used in the
compounding of certain bitters. The chief constituents of
senna are carthartic acid, sennacrol, sennapicrin, chryso-
phanic acid, emodin and cartharto-mannite (sugar). See
Pharm. Journ., ii./13, 741, and Chem. & Drug., ii./13, 743,
for further description of constituents.
Simaruba Bark. ^This is the root bark of Simaruba
officinalis or Mountain Damson. It is very bitter and
astringent to the taste, but has no odour. The chief
constituents are a crystalline, bitter glucoside, a yellow
resin and a brown resin (Chem. & Drug., i./08, 600).
MISCELLANEOUS FLAVOURING MATERIALS 49
Squaw Vine or Partridge Vine (Checkerberry). This
is the herb Mitchella repens. It has a bitter, astringent
flavour, but no odour. It has been used in flavouring
various materials, e.g. herbal beverages.
Tamarinds. These are the reddish-brown fruit of
Tamarindus indica, freed from the brittle outer pericarps.
Several varieties are on the market, e.g. West Indian, East
Indian and Egyptian. The West Indian type are preserved
in sugar; the East Indian are not preserved and the
Egyptian are marketed in a pressed condition. The
latter two varieties are used largely in pickles, sauces, etc.
The chief constituents are tartaric acid, citric acid,
potassium tartrate, acetic acid and sugar. Tests: They
should contain acid equivalent to 10 per cent, calculated
as tartaric acid, also the fruits should be free from copper.
Tansy. This is the flowering herb, Tanacetum vulgare,
which is grown in Europe and North America. It has a
strong, unpleasant odour and a bitter, aromatic taste. Its
content of essential oil is 0*1 to 0*3 per cent.
Thyme. This is the fresh herb Thymus vulgaris, which
is grown in European countries. It has a characteristic
aromatic flavour and is extensively used for culinary
purposes. Its flavour is due to its content of 0'3 to 2 '6
per cent, of a volatile oil.
Tonka Beans. These are the seeds of Dipteryx odorata,
which is indigenous to tropical South America. They
contain the well-known and widely used flavouring
material coumarin, to the extent of about 1*5 per cent., and
also sugar, malic acid, fixed oil, gum and fibre (Journ.
Pharm. Chim., ii. 480). The beans vary in size and
appearance according to derivation. Surinam beans are
grey and large ; Angostura are slenderer, long and shining,
Para being shorter and smaller. In their preparation for
4
50 FLAVOURING MATERIALS
the market, the beans are soaked in rum and this causes
them to shrink and assume a grey efflorescence composed
of crystals of coumarin. The odour of both tonka beans
and coumarin resembles that of new-mown hay. The
beans have a wide range of applicability in flavouring
materials suitable for use in confectionery, tobacco, etc.,
as well as being occasionally employed to cheapen vanilla
extract.
Valerian. This is the dried, erect root of Valeriana
officinalis and V. wallichii collected in autumn. The
plants are grown chiefly in Europe and Asia. The root
has a strong, unpleasant odour which develops during
drying, and a camphoraceous, bitter taste (Journ. Chem.
Soc. t 1921, i. 488). Its volatile-oil content is 0'5 to 1-0
per cent. Tests : Ash, 8 to 10 per cent.
Vanilla. Vanilla beans of commerce are the dried,
fermented pods of the climbing orchids Vanilla planifolia
and V. pompona, which are indigenous to tropical America.
They are chiefly cultivated in Mexico, Reunion, Tahiti,
Java, the Seychelles, Fiji and the West Indies. The
fruit is gathered when ripe in the autumn, and it is
fermented and dried, either by the sun or in warm
rooms, the method of process depending on the customary
practice in the production areas (Agric. News, vi. 291).
The beans, as they appear on the market, are brown-
black in colour, 8" to 10" long and J" to f" thick. The
longest varieties, e.g. Mexican, are usually the best, these
frequently having a coating of fine vanillin crystals, which
is termed frost or "givre." Busse, Zeits. Unter. NaJir.
Cf-enussm., 1899, 519, gives the following figures as regards
vanillin-content for vanillas of various derivations :
Mexican, 1'69 to T86 ; Bourbon, 1-91 to 2'90; Java,
275; Ceylon, 145; German East Africa, 216; Tahiti,
MISCELLANEOUS FLAVOURING MATERIALS 51
T55 to 2 ! 02. Other constituents of vanilla beans are
vanillic acid, resin, sugar, fat and mineral matter.
Exhausted vanilla heans coated with crystals of benzoic
acid, which may readily be detected by the microscope,
are sometimes offered on the market.
Vanilla extract is prepared from vanilla beans, alcohol
and sugar in the following approximate proportions :
Vanilla beans sliced, 10 : sugar, 20 ; alcohol, 65 ; water,
35. Sometimes glycerine is substituted for the sugar, the
colour of the extract being thereby deepened owing to
more extractive matter being drawn from the beans.
Dilute alkali is also occasionally used in extracting
vanilla beans, an economy in the amount of alcohol
required being effected ; the quality of the essence, how-
ever, suffers considerably.
Vanilla extracts are sophisticated by the use of
coumarin, tonka bean, caramel, acetanilide, etc. Vanilla
extract gives a heavy precipitate with lead acetate;
extracts which do not contain natural vanilla usually
give no precipitate or only give a slight cloudiness due
to the presence of caramel. Hess (Journ. Am. Chem. Soc.,
1899, 21, 721) precipitates the resinous matter from the
extract by means of dilute hydrochloric acid. After
separation, this resin is re-dissolved in alcohol and a few
drops of ferric chloride added. If the extract is genuine
no coloured precipitate should be obtained.
Several methods have been devised for the estimation
of vanillin and the detection and estimation of coumarin
in vanilla extracts. The following is an example : 50 gms.
of the extract are diluted with 30 c.c. of water, evaporated
to 50 c.c. on the water bath, again diluted with 30 c.c. of
water and evaporated to 50 c.c. Twenty-five c.c. of lead
acetate (containing 8 gms. of crystalline lead acetate per
52 FLAVOURING MATERIALS
litre) are added and the solution made up to 100 c.c.
After shaking, the mixture is allowed to stand for a day
and filtered. Fifty c.c. of the filtrate are treated with
65 c.c. of ether, in small quantities at a time, in a separat-
ing funnel. The ethereal extract is shaken several times
with 2 per cent, ammonia solution (up to 20 c.c. being
used). The residual ether extract is evaporated in a
tared dish at 20 to 25 C., dried over sulphuric acid and
weighed as Coumarin. The coumarin should be soluble
in petroleum ether; if, however, a residue remains after
treatment with this solvent it should be weighed and
tested for Acetanilide. The above-mentioned ammoniacal
solution, after separation from the ether extract, is slightly
acidified with hydrochloric acid and shaken in a separating
funnel with ether as in the previous extraction. The
ether extract is evaporated at a low temperature, dried
over sulphuric acid and weighed as Vanillin.
T. von. Fellenberg has devised a process, which is given
in the Journ. Chem. Soc., 1916, ii. 355, for the colorimetric
estimation of vanillin in vanilla extract.
For the detection of coumarin in vanilla extract,
Wichmann distils the extract, evaporates the distillate to
dryness and fuses the residue with caustic potash, thus
converting the coumarin into potassium salicylate, which
can be estimated colorimetrically, using ferric chloride
solution. Dean, in the Journ. Ind. Eng. Chem., 1915, 519,
proposes a method which is not interfered with by
saccharine or salicylic acid (see also Analyst, 1918,
325).
Winton, Albright and Berry (Journ. Ind. Eng. Chem.,
1915, 516 to 519) give the results of the estimation of
acidity and ash of a number of samples of vanilla extract
prepared from several varieties of vanilla beans. Methods
MISCELLANEOUS FLAVOURING MATERIALS 53
for the estimation of vanillin in flavouring extracts are
given in the Analyst, 1912, 501 ; 1917, 1*7, 208.
Virginia Snake Root. This is the root of Aristolochia
serpentaria or serpentary rhizome, which is obtained from
the southern regions of North America. It is a bitter,
with stomachic properties, after the type of columba ; its
taste is aromatic and bitter, resembling to some extent
valerian, camphor and turpentine. Its essential - oil
content is I/O to 2'0 per cent. Tests : Ash, 7 to 10
per cent.
White Cinnamon. This is the fawn-coloured, quilled
bark of Canella alba, which is grown in the West Indies.
It has a biting, aromatic odour, resembling cinnamon.
Its volatile-oil content amounts to 0*75 to T25 per cent.
Wild Cherry Bark. This is the greenish-brown bark
of the North American plant Prunus serotina or Virginian
Prune, collected in the autumn. It contains amygdalin
and emulsin, which develop hydrocyanic acid when mixed
with water. Its flavour, when soaked in water, is of a
bitter almond type. It is said to yield 0'2 per cent, of
volatile oil and 0*075 per cent, of hydrocyanic acid. A
syrup prepared from wild cherry bark is used for cover-
ing the taste of nauseous drugs. The bark is also used in
herbal beverages. Tests : Ash, 3 to 4 per cent., not over
6 per cent. For the identification of spurious cherry
barks, see Pharm. Journ., 1./09, 192, ii./lO, 604.
Woodruff. This is the herb Asperula odorata. It has
a flavour resembling coumarin.
Wormwood. This comprises the leaves and flowering
tops of the herb Artemisia absinthium, which is grown in
Europe and North America. It has a very bitter taste
and an odour resembling thujone. It contains a bitter
principle absinthin, which is slightly soluble in water,
54 FLAVOURING MATERIALS
but easily soluble in alcohol, ether and chloroform. Its
volatile-oil content is 0*5 per cent. It is used in bitters
and, together with anise, coriander, etc., in the liqueur
absinthe, also, along with angelica, etc., in vermouth.
Yarrow. This is the herb Achillea millefolium. It
has an insipid flavour and a very weak odour. It contains
about 0*23 per cent, of a volatile oil.
Zedoary Root. This is the root of Curcuma zedoria,
which is grown in Ceylon. It has a bitter and camphor-
aceous flavour, and an odour resembling ginger and
cardamoms. It is used in bitters. Its volatile-oil content
varies between O06 and 0'25 per cent.
BALSAMS, RESINS, ETC.
Benzoin. This is a resin derived from the tree Styrax
benzoin, which is grown in Sumatra, Siam, Penang, Java,
Saigon, Palembang, etc. The resin exudes from incisions
in the trees and is exported either in masses or tears.
Cocking and Kettle at the British Pharmaceutical Con-
ference (see P. & E.O.R., 1914, 331) gave the analytical
constants of benzoin of various derivations (see also Journ.
Chem. Soc., 1921, i. 351, 352). Sumatra benzoin contains
up to 18 per cent, free and combined benzoic acid and
rather more free and combined cinnamic acid. Siam
benzoin contains up to nearly 40 per cent, free and com-
bined benzoic acid. Other constituents of benzoin are
vanillin, phenyl-propyl-cinnamate, styrol, etc.
Peru Balsam. This is a dark brown, thick liquid,
which is obtained from the trunk of Myroxylon pereira, a
tree growing in the forests of San Salvador. The method
of extracting the balsam is described in the P & E.O.R.,
1918, 281. It has a bitter taste and an aromatic odour.
Its chief constituent is cinnamein (55 to 65 per cent.),
MISCELLANEOUS FLAVOURING MATERIALS 55
which consists of a mixture of benzyl benzoate and
benzyl cinnamate. It also contains resins and alcohols.
A description of the methods of testing Peru Balsam are
given in the P. & E.O.R., 1912, 203 (see also Journ. Chem.
Soc., 1921, ii. 226). The B.P. specific gravity limits are
1-140 to 1158. As regards the alcohol contained in the
balsam, namely, peruviol, this was isolated in 1899 by
Thorns, and has been investigated by Schimmel & Co.
It has the following characters : specific gravity, T1200 ;
optical rotation, 55'; refractive index, 1-5718; acid
value, 364; ester value, 228'2.
Styrax. This oleo-resin is derived from the inner bark
of Liquidambar orientalis, which grows in forests in south-
west Asia Minor. Its chief constituents are cinnamic
acid, both free and combined, and cinnamic alcohol.-
Much sty rax has been sold from which the odorous
constituents have been extracted. The oleo-resin is grey
in colour and contains 20 to 30 per cent, water. Its
content of cinnamic acid is 20 to 30 per cent. It is
purified by dissolving in ether or alcohol, filtering and
distilling off the solvent. See Analyst, 1912, 499, for a
description of the examination of styrax.
Tolu Balsam. This is obtained by making incisions in
the trunk of Myroxylon toluifera, which grow in New
Granada and Venezuela. It is at first soft, but later
becomes harder and finally becomes brittle. Its chief
constituents are free and combined cinnamic acid (about
35 per cent.), benzyl benzoate, benzyl cinnamate, vanillin,
a volatile oil and resin. The P. & E.O.E. gives analytical
notes in the following issues: 1911, 277; 1912, 202;
1913,293; 1915,89, 124.
56 FLAVOURING MATERIALS
ANIMAL PRODUCTS
Ambergris. This is an excretion of a morbid nature
from the sperm whale, Physeter macrocephalus. It is
obtained chiefly from the coasts of Sumatra, Java, and
Madagascar. The grey variety, which is the most valu-
able, is opaque, solid, and with a granular fracture. It is
frequently streaked with yellow. The black variety is
plastic to the touch. Ambergris contains about 85 per
cent, ambreine, which is soluble in alcohol ; it also contains
benzoic acid. It has a specific gravity of 0*91.
Castoreum. This consists of the dried, preputial follicles
of the beaver, Castor fiber, and is obtained from Canada,
Eussia, Siberia, etc. It is placed on the market in sacs,
2" to 3" in length, the contents of which are reddish-
brown in colour and have a characteristic odour.
Castoreum varies in composition according to derivation.
The chief constituents are a resinous body (40 to 70 per
cent.) which is soluble in alcohol, a volatile oil, benzoic
acid, castorin (Bull, de Pharm., 1897), salicin, salicylic
aldehyde, albuminous matter, inorganic salts, and mucus.
Adulteration is sometimes practised with resin, dried
blood, wood fibre (P. & E.O.R., 1913, 14), etc. Castoreum
is liable to deterioration unless kept perfectly dry and in
a cool place.
Civet. This substance is obtained from the civet glands
of several species of cats. The bulk of the civet of com-
merce is obtained from the African or Abyssinian civet
cat, Viverra civetta ; other species yielding civet are the
Indian cat, V. zibetta ; the Burmese cat, V. megaspila ; the
Malabar cat, V. civettina ; the Chinese cat, V. malaccensis ;
the Javan cat, V. tangalunga, etc. Civet is usually semi-
solid and dark-coloured when it arrives on the market.
It also has a very disagreeable odour. Its use is practic-
MISCELLANEOUS FLAVOURING MATERIALS 57
ally confined to fixing other perfumes, being employed in
very small amounts in certain extracts and essences. 1 1
is subject to adulteration with fats of both mineral and
vegetable origin, and also banana pulp. When dried and
extracted with hot acetone it should yield 80 per cent,
extract. The following are the chief characters of civet :
Moisture, 10 to 30 per cent.; ash, 1 to 2 per cent.;
petroleum ether extract, 80 per cent, upwards (P. & E.O.R.,
1913, 348); acid value of petroleum ether extract, 130
to 150 ; melting point, 43 to 46 ; saponification value,
130 to 150.
Musk. This is the dried secretion of the preputial
follicles of the musk deer, Moschus moschiferus, obtained
from Central Asia. The most valued variety is Tonquin
musk. " Grain " musk is obtained by drying the contents
of the pods, which are cut from the animals. The odour
of natural musk is due to its content of 0'5 to 2 per cent,
of a ketone-like substance niuskone (P. & E.O.E., 1916,
133), besides which is present also fatty matter, proteins
and resins. Tests : Ash, not more than 8 per cent. ;
moisture, about 30 per cent. The U.S.P. limits moisture
to 15 per cent., the figure being obtained by drying over
sulphuric acid. 10 to 12 per cent, is soluble in 95 per
cent, alcohol, and 50 to 75 per cent, is soluble in water.
The Suriss P. states that about 10 per cent, is soluble in
90 per cent, alcohol and 50 per cent, in water.
SECTION II
ESSENTIAL OILS
CHAPTEK V
THE PKEPAKATION AND ANALYSIS OF
ESSENTIAL OILS
THE three chief processes used in the recovery of essential
oils are (1) distillation, (2) extraction and (3) expression.
The process used varies according to the material under
treatment, the particular nature of the oil and its resistance
to varying degrees of heat.
Distillation. The majority of essential oils are obtained
by distillation processes. The old method of distillation
consisted in heating over an open fire a large still con-
taining the vegetable material and water. This has been
displaced to a great extent by steam distillation, using
either saturated steam under pressure or superheated
steam. The general principle of such distillation is to
heat the material in the still by means of a steam coil
and at the same time to blow steam through the mass.
The vegetable material is usually separated from the
bottom of the still by a false bottom, through the per-
forations of which live steam is blown from a perforated
coil situated beneath.
Distillation under reduced pressure is practised in some
58
THE PREPARATION OF ESSENTIAL OILS 59
cases where the volatile constituents of the oil are subject
to decomposition. Terpeneless and sesquiterpeneless oils
are produced in this manner.
Certain processes of continuous distillation have been
devised for the production of essential oils. The dis-
tillation of essential oils is, however, a matter of con-
siderable skill and experience ; variations have to be
made in the methods of distillation according to the
material under treatment. The preparation of the
vegetable material for distillation also requires experi-
ence; for example, seeds, barks, rhizomes, etc., are
usually dried and ground, woods are rasped or ground,
and green, soft material is distilled in many cases without
preliminary treatment.
Extraction. The preparation of essential oils by
extraction from flowers, etc., with volatile solvents is
described later in Section III.
Expression. This method is used particularly in the
case of the citrus oils, e.g. lemon, bergamot, orange, etc.
The procedures adopted vary in different countries. In
some cases the rinds of the fruits are placed in cloths and
subjected to great pressure. This squeezes out a cloudy
fluid which is allowed to stand in tall vessels for several
days for separation to occur, the atmosphere being excluded
as much as possible.
One of the chief expression processes is the sponge,
Sponge or spugna method, which is used principally in
Sicily and Southern Italy. This consists in ejecting the
essential oil from the glands just under the skin of the
fruit by pressing the convex pieces of rind against a
sponge until they become practically flat. The sponge
absorbs the oil and is squeezed periodically. The Scorzetta
method is similar to the above, except that the fruits
60 FLAVOURING MATERIALS
are halved, and the skins after pressing remain unbroken,
being subsequently packed in brine and exported for use
in the production of preserved and candied peels.
The ecudle method of obtaining citrus oils, which is
practised in France and Northern Italy, consists in
rolling the fruits in a bowl-shaped vessel, the interior
of which is covered with short spikes. The oil cells
are ruptured and the oil is collected from the apparatus
in a tube.
Several machine processes for the production of citrus
oils have been invented and worked with varying degrees
of success. The P. & E.O.R., 1916, 73, makes reference to
a method of extracting lemon oil in which the lemons in
a broken condition are treated with a certain acid which
causes the oil to separate and rise to the surface. About
2*5 per cent, more oil is said to be obtained by the process
than by the sponge method.
GENERAL ANALYTICAL METHODS
Physical Tests. Specific Gravity. This is usually
determined on the Westphal balance at a temperature
of 15 C. In the case of small quantities the determina-
tion is made by means of a specific gravity bottle,
Sprengel tube or pycnometer. Oils which are solid at
15 C., such as aniseed and otto of rose, are tested
at 20 C.
Optical Rotation. This is determined at 20 C., using a
100 mm. tube in a polarimeter reading in angular degrees.
The specific rotation or [a] D is calculated by dividing the
angular rotation by the density of the oil.
Refractive Index. This is usually determined at a
temperature of 20 C. on an instrument of the Abbe
type. It is sometimes more convenient to make the
THE PREPARATION OF ESSENTIAL OILS 61
test on some oils at a temperature of 25 C. ; these oils
are noted in Chapter II.
Congealing-Point. This is a test which, along with the
melting-point, is of great importance in the testing of
aniseed oils. The determination is made by taking 5 c.c.
of the oil in a test tube and immersing same in a cooling
bath at a temperature of 10 C. It is stirred by means of
a thermometer graduated in tenths of a degree. When
the oil begins to solidify, the tube is removed and placed
in a bath at a temperature of 14 C. and the oil stirred
continuously. The temperature rises and then falls again,
the maximum point reached being the congealing-point.
Several tests are made and the mean taken. When a
similar determination is to be made on fennel oil it is
usual to employ a freezing mixture of ice and salt or to
maintain the temperature at or lower.
Melting-Point. This is determined by placing the pre-
viously congealed oil contained in a test tube in a water
bath at a temperature approaching that at which the oil
should melt, and very gradually increasing the temperature
of the water bath. The temperature at which the oil is just
melted is read off on a thermometer graduated in tenths.
Boiling-Point. This is determined by distilling a small
quantity of the oil in an ordinary distillation flask, noting
the temperature registered and correcting to a pressure of
760 mm. Extreme accuracy is obtained if the portion of
the thermometer which is not surrounded by the vapour
is allowed for according to the formula
(0-0001430
T' being the temperature observed, n the number of
degrees exposed and t the temperature of the exposed
part of the thermometer.
62 FLAVOURING MATERIALS
CHEMICAL TESTS
General Methods. Esters. The ester value of an
essential oil is the difference between its acid value and
its saponification value. The acid value, which is the
number of milligrams of potash required to neutralise
1 gm. of oil, is estimated by dissolving 3 to 5 gms. of the
oil in 15 to 20 c.c. of neutral alcohol and titrating with
N/10 alcoholic potash, using phenol phthalein as indicator.
The saponification value is estimated by boiling 3 to 5 gms.
of the oil with 20 c.c. normal alcoholic potash under a
reflux condenser for one hour and titrating the excess of
alkali with normal sulphuric acid. The result is expressed
in terms of the number of milligrams of potash absorbed
by 1 gm. of the oil. The percentage of esters in an oil,
which is usually expressed as the ester present in pre-
dominating quantity, is calculated from the formula
MX NX 100,
TOOOxW
M being the molecular weight of the ester, N the number
of c.c. normal caustic potash absorbed and W the weight
of the oil.
An interesting report is given in the P. & E.O.R., 1915,
218, of a research on the rate of saponification of linalyl,
terpinyl and geranyl acetates. Terpinyl acetate saponifies
much more slowly than geranyl and linalyl acetates. The
necessity of using efficient condensers in the saponification
process is pointed out in the P. & E.O.R., 1914, 251.
Alcohols. The usual method of estimating the per-
centage of alcohols in an essential oil is by acetylation
followed by saponification. The method is as follows :
Ten c.c. of the oil are boiled with 20 c.c. of acetic anhydride
and 2 gms. of anhydrous sodium acetate, under a reflux
THE PREPARATION OF ESSENTIAL OILS 63
condenser, for two hours. The liquid is diluted with
about 100 c.c. of water and allowed to stand for several
hours in the water bath. The oil is then washed in a
separating funnel with several lots of distilled water or
with brine containing 1 per cent, of caustic potash.
Finally, the oil is dried over anhydrous sodium sulphate
and filtered. The percentage of esters in the acetylated
oil is then estimated by a similar saponification process to
that given above for Esters. The percentage of alcohols
is calculated from the formula
MxN
10(W-0-042N)
M being the molecular weight of the alcohol, N the
number of c.c. of normal caustic potash absorbed and W
the weight of the acetylated oil taken. The formula only
answers when the original oil contains no esters. T. T.
Cocking has an interesting method of calculating the per-
centage of alcohols in presence of esters in the P. & fi.OM.,
1918, 37.
It is important if concordant results are to be obtained
that the acetic anhydride and anhydrous sodium acetate
used are of a high degree of purity. It is advisable that
freshly fused sodium acetate be used and that the acetic
anhydride should have a specific gravity of at least 1*080
and contain upwards of 95 per cent, of acetic anhydride.
Low results are given by some alcohols, e.g. linalol and
terpineol, owing to decomposition. Also, it is possible to
estimate citronellal by this method as this aldehyde is
converted quantitatively into isopulegyl acetate by
acetylation.
The determination of citronellol and citronellal in
essential oils by a process of formylation has been used
64 FLAVOURING MATERIALS
quite extensively of late years. C. T. Bennett, in the
P. & E.O.R, 1921, 12, 351, points out, however, that this
formic acid method is absolutely untrustworthy.
Aldehydes and Ketones. (a) The old method consists
in absorbing the aldehyde or ketone by means of a
35 per cent, solution of sodium bisulphite. Five to 10 c.c.
of the oil are measured into a 200 c.c. flask, which has a
neck graduated in l/10th c.c. One hundred and fifty c.c.
of the bisulphite solution are added and the mixture
heated on the water bath for one to two hours with
constant shaking, or until the solid bisulphite-aldehyde
(or -ketone) compound formed is dissolved. The un-
combined oil is forced into the graduated neck by adding
more solution. The flask and its contents are allowed to
cool for twelve hours and the volume of uncombined oil
read off. A simple calculation gives the percentage of
aldehyde or ketone which has been absorbed by the bi-
sulphite solution. This method is used for cassia and
lemon-grass oils.
(6) The B.P. 1914 recommends the following neutral
sulphite method for the determination of aldehydes in
cinnamon and lemon-grass oils : 5 c.c. of the oil are
carefully measured into a similar flask to the one used in
method (a). Twenty-five c.c. of a 20 per cent, solution of
sodium sulphite and several drops of phenol-phthalein
solution are added. The mixture is heated on a water
bath with constant shaking, a 10 per cent, solution of
acetic acid being added from time to time in sufficient
quantity to keep the contents of the flask neutral.
When no further alkali is liberated, which is usually the
case at the end of about fifty minutes, the unabsorbed oil
is forced into the graduated neck of the flask and measured
after cooling for twelve hours.
THE PREPARATION OF ESSENTIAL OILS 65
Phenols. Five to 10 c.c. of the oil are placed in a flask
similar to that used in the determination of aldehydes and
ketones and 100 c.c. of 5 per cent, caustic potash solution
added. The mixture is heated in a water bath for one
hour, with frequent shaking. The unabsorbed oil is then
forced into the graduated neck of the flask and measured
after cooling for twelve hours. The " absorbed " portion
of the oil represents phenols and a simple calculation gives
the percentage contained in the oil. The phenols con-
tained in pimento, clove, thyme, origanum, bay, cinnamon
leaf, etc. oils are estimated in this manner.
Adulterants. The chief adulterants used in the sophisti-
cation of essential oils are resin, mineral oil, alcohol,
acetone, chloroform, artificial esters such as terpinyl
acetate, etc., turpentine oil, fatty oils, terpenes, copaiba
oil, gurjun balsam oil, cedar wood oil, etc. Resin may be
detected and estimated in cassia oil by adding a solution
of lead acetate in 70 per cent, alcohol to a solution of the
oil in 70 per cent, alcohol and weighing the precipitate
formed (P. & E.O.R., 1914, 264). Mineral Oil is less
soluble in alcohol than most essential oils ; it is also un-
saponifiable and has a low refractive index and specific
gravity. Alcohol, acetone and chloroform distil at com-
paratively low temperatures. Alcohol and acetone give
the iodoform reaction and chloroform the phenyl iso-nitrile
test. Artificial esters, such as terpinyl acetate, glycerine
acetate, ethyl tartrate, citrate, phthalate, etc., distil in
the last fractions of the oil. Terpinyl acetate can be
identified by a method (P. & E.O.R., 1915, 148) based on
the protracted period which is necessary to complete its
saponification by alcoholic potash. A special method
has been devised by Schimmel & Co. (P. & E.O.R., 1915,
147) for the detection of terpinyl acetate. Turpentine
5
66 FLAVOURING MATERIALS
frequently reduces the specific gravity of an oil and
influences the optical rotation of the first fractions which
are obtained when the oil is distilled. Fatty oils leave an
oily stain when the oil is allowed to evaporate on blotting-
paper. Also, with the exception of castor oil, they are
insoluble in alcohol. Terpenes, which are sometimes
added to lemon, orange, etc. oils, lower the specific
gravity and increase the optical rotation. Copaiba, gurjun
balsam and cedarwood oils have high specific gravities and
distil in the last fractions of the oil. When several drops
of nitric acid are added to gurjun balsam oil a deep violet
colour is obtained.
Special Methods. These are very numerous and are
being continually added to, so that it is proposed to
summarise the most important and briefly refer to several
recently introduced methods, leaving the reader to scan
current literature dealing with analytical chemistry if it
is desired to keep pace with the most modern methods.
Citral in Lemon Oil. This is estimated according to
the method given in the B.P., 1914. Twenty gms. of the
oil are weighed into a 200 c.c. flask, 20 c.c. of absolute
alcohol and 20 c.c of N/2 hydroxylamine hydrochloride
in 80 per cent, alcohol added. This hydroxylamine
hydrochloride solution contains 35 gins, hydroxylamine
hydrochloride per litre and is standardised against
semi-normal acid. Eight c.c. normal alcoholic potash are
added, the mixture is boiled under a reflux condenser
for thirty minutes and then cooled The mixture in the
flask is diluted with 250 c.c. of distilled water, which are
added through the reflux condenser with a view to wash-
ing same. A few drops of phenol-phthalein are added
to the solution and normal caustic potash added until
the solution is neutral. The contents of the flask are
THE PREPARATION OF ESSENTIAL OILS 67
then titrated with semi-normal hydrochloric acid, using
methyl orange as indicator. A blank experiment is
carried out and the number of c.c. of semi-normal hydro-
chloric acid required by this blank test, in excess of those
required by the main test, represents the amount of
hydroxylamine which has been taken up by the citral.
When this is multiplied by 0'076 the amount of citral in
the oil taken is obtained.
Citral in Terpeneless Lemon and Lemon-grass Oils. This
is best determined by the neutral sulphite method given
under "Aldehydes." In the case of terpeneless lemon
oils the bisulphite method gives erratic figures and in the
case of lemon-grass oil higher results, by about 4 or 5 per
cent., are obtained using the bisulphite method than when
the neutral sulphite method is employed.
In the Analyst, 1910, 125; 1918, 379, the Hiltner
method of estimating citral by colorimetric means,
together with a modification of the same, is described.
The reagent employed is metaphenylenediamine hydro-
chloride, with the addition, in the modification, of oxalic
acid.
Cineol in Eucalyptus and Cajuput Oils. Several
methods have been suggested for this estimation, the one
in most common usage is, however, that involving the use
of phosphoric acid. Five c.c. of phosphoric acid (S.G.
1'75) are added to 10 c.c. of the oil contained in a
porcelain basin, which is cooled by means of a freezing
mixture. The contents of the basin are stirred with a
glass rod until a solid mass is formed. This is placed in
calico and pressed between blotting-paper in a strong
press for several hours. The solid cake is then trans-
ferred to a graduated measure, 25 c.c. of cold water
added and, after standing twelve hours, the volume of
68 FLAVOURING MATERIALS
oil is read off. Arsenic acid may be used in a similar
manner to phosphoric acid for the determination it has
the disadvantage, however, of being extremely poisonous.
A method is given in the Analyst, 1920, 457, for the
estimation of cineol in eucalyptus oil by the determina-
tion of the solidifying point of the oils. T. T. Cocking
also proposes to estimate cineol by means of the solidify-
ing point of a mixture of the oil and o-cresol.
The B.P. test for phellandrene in eucalyptus oils is as
follows : Two c.c. of the oil are mixed with 2 c.c. of
glacial acetic and 2 c.c of saturated sodium nitrite
solution. If phellandrene is present crystals of phellan-
drene nitrosite separate out. A more sensitive test is
obtained by the addition of 5 c.c. of petroleum ether to
the mixture.
A method of testing for cineol in phellandrene oils is
given in the Journ. Soc. Chem. Ind. y Aug. 31, 1918.
The reagent used is iodol, which gives a crystalline com-
pound with cineol.
Citronellal and G-eraniol in Citronella Oils. These are
estimated by Dupont and Labaune's method as follows :
Ten gms. of the oil are shaken for two hours at 15 to
18 C. with a mixture made up as- follows : 10 gms. hydro-
xylamine hydrochloride are dissolved in 25 c.c. water and
10 gms. of potassium carbonate, dissolved separately in
25 c.c. water, added, the mixture being then filtered.
The oil is separated, dried over anhydrous sodium
sulphate and acetylated with acetic anhydride and fused
sodium acetate for one and a half hours under a reflux
condenser. The resultant oil is washed, dried and
neutralised and about 2 gms. taken and saponified with
alcoholic potash. The total " geraniol and citronellal "
figure is obtained from the total acetylisable constituents,
THE PREPARATION OF ESSENTIAL OILS 69
which are estimated in the ordinary manner, and the
quantity of citronellal, which is converted into nitrile in
the above estimation and remains unaffected by the
potash, is calculated by difference, the geraniol being
calculated by the usual formula.
Prussic Acid in Oil of Bitter Almonds. Two methods
are in general use (1) which is gravimetric, is as
follows: 1 to 1'5 gms. of the oil are dissolved in about
10 c.c. alcohol, 10 c.c. of ammoniated alcohol added and
the mixture allowed to stand for half an hour. A small
quantity of nitric acid is then added to acidulate the
mixture and the cyanide precipitated with silver nitrate.
The solution is filtered and the precipitate dried to
constant weight in a water oven and weighed. The per-
centage of prussic acid is calculated from the formula
Weight of silver cyanide x 20179
Weight of oil taken
(2) The volumetric method of estimating the amount
of prussic acid consists in titrating a 10 per cent, solution
of the oil in alcohol with N/10 silver nitrate solution,
using potassium chromate in alkaline solution as indicator,
after allowing for the chloride present in the reagents
employed.
Artificial Benzaldeliyde. This is usually detected in a
natural oil by means of the trace of chlorine which it
nearly always contains.
Lead in Cassia Oil. A rapid method for the colori-
metric estimation of lead in cassia oil by means of
ammonium sulphide is given in the Journ. Soc. Chem. Ind.,
1920, 39, 35-36.
CHAPTEK VI
SYSTEMATIC SUKVEY OF THE ESSENTIAL OILS
IN the following systematic survey of the essential oils
the usual method of classification is adopted, namely,
according to the botanical derivation of the oils.
Coniferae. Cedar Oil. This is obtained from the
Virginian red cedar, Juniperus mrginiana. The wood oil
is distilled from the refuse of pencil factories, the yield
being 2*5 to 5 per cent. The chief constituents of the
oil are the sesquiterpene cedrene, about 7 to 10 per cent,
of cedrol, which is a crystalline body melting at 78 to
80 when pure, and cedrenol (P. & E.O.R., 1912, 107).
Characters: Specific gravity, 0'940 to 0'960; optical
rotation, -25 to -44 ; refractive index, 1495 to 1-510 ;
soluble in 10 to 20 vols. of 90 per cent, alcohol ; 80 per
cent, of the oil distils between 125 and 155 at a pressure
of 14 mm. (Schimmel).
The leaf oil contains limonene, borneol, cadinene, bornyl
esters, etc. Characters : Specific gravity, 0'883 to 0'888 ;
optical rotation, +55 to +65. Oils distilled from the
leaves of Thuja occidentalis and Chamce cyparis sphceroidea
are often sold as cedar leaf oils.
Juniper Berry Oil. This is obtained, to the extent of
about 0'8 to 1-5 per cent., by distillation of the beans of
Juniperus communis, which is indigenous to Greece, but
most extensively grown in Italy and Hungary (P. &
SYSTEMATIC SURVEY OF ESSENTIAL OILS 71
E.O.R., 1915, 63). The chief constituents of the oil are
25 to 60 per cent, pinene, 15 to 25 per cent, cadinene,
juniper camphor (a sesquiterpene alcohol melting at
165 to 166) and a small quantity of esters boiling at
about 180. Juniper oil is largely used in the flavouring
of artificial gin. Characters: Specific gravity, 0'862 to
O890 ; optical rotation, 3 to 15; refractive index at
25, 1472 to 1-488; soluble in 4 vols. of 95 per cent,
alcohol when fresh. The specific gravity increases and
the solubility decreases with age (P. & E.O.R., 1913, 402 ;
1914, 5).
Juniper Wood Oil, which is used as a substitute for
the berry oil, is usually a mixture of the latter with
turpentine.
Pine-Needle, Oil. This is distilled chiefly from the
leaves of Pinus pumilio and P. sibirica, the oil from the
latter being the 01. Abietis of the RR, 1914. The oil
from P. pumilio is obtained principally from Hungary
and the Austrian Tyrol ; its constituents are : sylvestrene,
1-phellandrene, small amounts of 1-pinene, cadinene,
dipentene and 5 to 7 per cent, of esters, chiefly bornyl
acetate. Characters: Specific gravity, 0'863 to 0'875;
optical rotation,- 6 to - 14; refractive index at 25, 1475
to 1-485. The oil distilled from P. sibirica is obtained
chiefly from Northern Eussia and the Urals. Its chief
constituents are 30 to 45 per cent, esters (Chem. & Drug.,
ii./ll, 68), these being chiefly bornyl acetate, also pinene,
dipentene, camphene, phellandrene, etc. Characters :
Specific gravity, 0'900 to 0'930; optical rotation, -30 to
-45; refractive index at 25, 1*467 to 1-476; soluble in
an equal volume of 90 per cent, alcohol (P. & E.O.R., 1915,
94). Pine-needle oils are largely used in the flavouring
of medicated sweetmeats, etc. See P. & E.O.R., 1915,
72 FLAVOURING MATERIALS
166, for characters of other pine-needle oils, e.g.
P. pectinata, P. sylvestris and P. canadensis.
Turpentine Oil. This is distilled from the oleo-resin
which exudes from several species of Pinus. American
turpentine oil, derived from Pinus australis and P. tceda,
is the chief of these products on the English market. It
contains chiefly pinene and a small amount of dipentene.
Characters : Specific gravity, 0*855 to 0*877 ; optical
rotation, +1 to +6 ; refractive index, 1465 to 1-480 ; 80
to 85 per cent, distils hetween 155 and 165. French
turpentine is derived from P. pinaster. Its chief con-
stituent is 1-pinene, the characters of the oil being as
follows : Specific gravity, 0*855 to 0'874 ; optical rotation,
-18 to -40; refractive index, 1470 to 1480; 75 to
90 per cent, distils between 155 and 165. Eussian and
Swedish turpentine oils are derived from P. sylvestris and
P. ledelourdii. They contain principally sylvestrene and
have a very disagreeable odour. Characters: Specific
gravity, 0*855 to 0'874; optical rotation, +5 to +16;
refractive index, about 1479 ; 30 to 70 per cent, distils
between 155 and 165. The various turpentine oils are
of no interest as flavouring agents ; from the American
oil, however, is obtained the liquid Terebene, which is
sometimes used in the flavouring of medicated lozenges,
etc.
Terebene. This is a colourless liquid produced by the
action of sulphuric acid on turpentine, followed by dis-
tillation. It consists principally of dipentine together
with other hydrocarbons. It has a specific gravity of
0*862 to 0-866, is optically inactive, boils at 160 to 170
and is soluble in 5 vols. of 90 per cent, alcohol.
Gramineaa. Citronella Oil. This is obtained, to the
extent of 0*5 to 1*0 per cent., by distilling the grass
SYSTEMATIC SURVEY OF ESSENTIAL OILS 73
Cymbopogon nardus (Andropogon nardus), which is grown
chiefly in Ceylon, the Straits Settlements and Java. The
chief constituents of the Ceylon oil are geraniol, citronellal,
dipentene, limonene, camphene, and small quantities of
methyl-heptenone, methyl-eugenol, linalol, borneol and
sesquiterpenes. The Java oil contains similar constituents,
the citronellal, however, predominating. Characters:
Ceylon Specific gravity, 0*900 to 0'920 ; optical rotation,
-7 to -16; refractive index, 1471 to 1-481; total
acetylisable constituents (as geraniol), 58 to 64 per cent. ;
soluble in 3 to 10 vols. 80 per cent, alcohol. Java-
Specific gravity, 0'885 to 0-910; optical rotation, to
-10; refractive index, 1-4650 to 1'4730 ; total acetylis-
able constituents (as geraniol), 80 to. 92 per cent. ; soluble
in 3 to 10 vols. 80 per cent, alcohol. Citronella oil is
used chiefly for the perfuming of cheap soap ; it is, how-
ever, interesting from the flavouring standpoint, as are
other members of the Gramineae, by reason of its geraniol
content. Much adulteration has been practised with
mineral oil, this having given rise to the controversy
regarding the Schimmel solubility test of the oil in 80
per cent, alcohol. The determination of the total acety-
lisable constituents in the oil is, however, now regarded
as the most satisfactory test. The following references
deal with the valuation of Java citronella oil : P. & E.O.R.,
1911, 201; 1912, 123, 250, 334; 1913, 13. For methods
of estimating the geraniol and citronellal contents, see
P. & E.O.R., 1912, 106; 1914, 275.
Ginger-grass Oil. This is derived from the ripened
grass Cymbopogon martini var. sofia. It is inferior to
palma-rosa oil (see later), containing more geranyl acetate
and having a distinct ginger odour. The chief constituents
of the oil are geraniol, dihydrocuminol, geranyl acetate
74 FLAVOURING MATERIALS
and small quantities of dipentene, limonene, carvone and
an aldehyde. Characters : Specific gravity, O930 to 0'945 ;
optical rotation, usually between +20 and +30, but as
wide variations as 30 to +54 have been observed;
refractive index, 1478 to 1*489 ; total alcohols (as geraniol),
35 to 70 per cent. ; esters, 5 to 25 per cent. ; soluble in
3 vols. 70 per cent, alcohol.
Lemon-grass Oil (Indian Verbena). This is derived
from the grasses Cyinbopogon citratus and C. flexuosus,
which are grown in Malabar and Cochin (C. flexuosus),
and in Ceylon, the Straits Settlements and the West
Indies (G. citratus). The chief constituents are citral,
geraniol, citronellal, methyl-heptenone, limonene and
dipentene, with additionally in the West Indian variety
an olefinic terpene which rapidly resinifies. Lemon-grass
oil is the chief source of citral, which it contains to the
extent of 70 to 85 per cent. (P. & KO.R, 1916, 95).
Characters : West Indian Oil Specific gravity, 0'877 to
0-887; optical rotation, -2 to 2; refractive index, 1483
to 1489 ; citral, 75 to 85 per cent. ; not soluble in 90 per
cent, alcohol. East Indian Oil Specific gravity, 0'895 to
0'905; optical rotation, 3 to +3; refractive index,
1-483 to 1488; citral, 70 to 80 per cent.; soluble in
3 vols. 70 per cent, alcohol (P. & E.O.R., 1914, 330, 398;
1916, 333, 394). The P. & E.O.R., 1918, 96, gives a note
regarding the constituents of a Formosan lemon-grass oil.
Palma-Eosa Oil (Indian Geranium Oil). This is derived
from the young bluish-white grass Cymbopogon martini
(Andropogon schcenanthus), which is grown chiefly in
India. It has a rose-geranium odour and contains chiefly
geraniol (75 to 95 per cent.), geranyl acetate, geranyl
caprylate and traces of dipentene, citronellol and methyl-
heptenone. Characters : Specific gravity, 0-885 to 0'895 :
SYSTEMATIC SURVEY OF ESSENTIAL OILS 75
optical rotation, 2 to +2; refractive index, 1/474 to
1*485 ; total alcohols (as geraniol), 75 to 95 per cent. ; esters,
5 to 11 per cent. ; soluble in 3 vols. 70 per cent, alcohol. It
is occasionally sophisticated by the addition of mineral oil,
fatty oils, turpentine, guijun balsam and cedarwood oils.
Veti-vert or Cuscus Oil. This is distilled, to the extent
of 0*4 to 0'9 per cent., from the roots of Vetivera zizanoides
(Andropogon muricatus\ which is grown in Bengal,
Punjaub, Reunion, Mauritius and the West Indies
(P. & E.O.R., 1913, 42). The chief constituents are
sesquiterpenes: Characters: Specific gravity, 1*015 to
1-030 (Reunion oil, 0*980 to 0'99o); optical rotation,
+ 25 to +45; refractive index, 1*517 to 1*520; esters,
less than 10 per cent. ; soluble in 2 vols. 80 per cent,
alcohol. The oil is sometimes adulterated with fatty oils.
MONOCOTYLEDONS
Aroideae. Calamus Oil. This oil is obtained, to the
extent of 1*5 to 3-5 per cent., by distillation from the
fresh rhizome of Acorns calamus or Sweet Flag, which is
grown in Europe, North America, China, Japan, Cochin
China and the East Indies. The chemistry of the oil is
not very well known. It contains eugenol, calamene (a
bicyclic terpene), asarone, calameon (similar in con-
stitution to cineol, melting-point, 119), traces of pinene
and oxygenated bodies. Characters : Specific gravity, 0'960
to 0*970; optical rotation, +10 to +35; refractive index,
1*506 to 1-508 ; soluble in 2 to 3 vols. 90 per cent, alcohol.
Iridaceae. Orris Oil. This is obtained, to the extent
of 0*1 to 0'2 per cent., by steam distilling the rhizome of
Iris floreniina, I. germanica and /. pallida, which are
grown in Mediterranean countries. It is a yellowish-
white mass, the chief odorous constituent of which is the
76 FLAVOURING MATERIALS
ketone irone, this being accompanied by about 85 per cent,
myristic acid and traces of esters. Characters : Acid
number, 200 to 220 ; melting-point, 08 to 50 ; saponifica-
tion value, 190 to 210 ; slightly dextro-rotatory ; soluble
in 16 vols. of 90 per cent, alcohol (P. & E.O.R., 1917, 275).
Orris oil is used in many flavouring essences as a sub-
stitute for or fixative of natural violet perfumes.
Liliaceae. Garlic Oil. This is obtained, to the extent
of 0'005 to O'Ol per cent., by distillation of the whole
fresh plant Allium sativum, which is cultivated extensively
in Spain, Portugal and Italy. It is used in Continental
countries as a flavouring agent. It contains chiefly diallyl
disulphide, and about 5 to 6 per cent, of allyl-propyl
disulphide. Characters : Specific gravity, T046 to 1*057.
It is optically inactive.
Onion Oil. This is distilled to the extent of 0*04 to
0'05 per cent, from Allium cepa. Characters: Specific
gravity, 1'036 to 1'041 ; optical rotation, about 5.
Zingiberaceee. Cardamom Oil. This is distilled to
the extent of 4 to 8 per cent, from the seeds of Elettaria
cardamomum, which grows in southern India and Ceylon
(P. & E.O.R., 1918, 69). The constituents of cardamom
oil are cineol, limonene, terpineol, terpinene and sabinene.
Characters : Specific gravity, 0'922 to 0'950 ; optical
rotation, +22 to +46; refractive index, 1-460 to 1-470 ;
soluble in 4 vols. of 70 per cent, alcohol. The P. & E.O.R.,
1918, 31, gives a note regarding the characters of a
cardamom oil distilled in Mysore.
Curcuma or Turmeric Oil. This is distilled, with a
yield of 5 to 5'5 per cent., from the rhizome of Curcuma
longa, which is cultivated in India, China and southern
Asia. The chief constituents of the oil are an alcohol
" turmerol," boiling at 285 to 290, and a small quantity
SYSTEMATIC SURVEY OF ESSENTIAL OILS 77
of phellandrene. The specific gravity of the oil is
0-940 to 0-945.
Galangal Oil. This oil is steam distilled, to the extent
of 0'5 to 1/5 per cent., from the rhizome of Alpinia galanga
and A. qfficinarum, which are cultivated in Siam and
China. It has a sharp taste and camphoraceous odour.
The chief constituents of the oil are cineol, eugenol,
cadinene and pinene. Characters: Specific gravity,
0-915 to 0-925; optical rotation, -1 to -4*; refractive
index, about 1480. Pimento and clove oils are the chief
adulterants; these are tested for by solubility. The oil
should not be entirely dissolved by an equal volume of
90 per cent, alcohol.
Ginger Oil. This is distilled to the extent of 1 to 3
per cent, from the rhizome of Zingiber officinale, which is
grown over a wide area in tropical Asia, the East and
West Indies and Africa. Its chief constituents are
zingiberine, phellandrene, camphene, and small quantities
of borneol, citral, cineol, etc. Characters : Specific gravity,
0-872 to 0-885 ; optical rotation, -25 to -45; refractive
index, 1-488 to 1495.
Grains of Paradise Oil. This is distilled, with a yield
of about 0-75 per cent., from the seeds of the Amomum
melegueta. Its odour is aromatic, being very similar to
cardamom oil, but not so fragrant.
Zedoary Oil. This is obtained to the extent of 1 to
2 per cent, by distillation of the roots of Curcuma zedoaria.
It has a camphoraceous odour due to the presence of
cineol. Its specific gravity is 0'990 to I'OIO.
DICOTYLEDONS
Anonaceae. Cananga Oil. This is derived to the
extent of 1-5 to 2 g per cent, from the flowers of Cananga
78 FLAVOURING MATERIALS
odorata, which is grown in the Philippines. The first
fractions which come over during the distillation are sold
as ylang-ylang oil (see later), the later fractions forming
the cananga oil of commerce. Both oils contain linalol,
geraniol, farnesol, nerol, iso-eugenol, cresol, paracresol,
pinene, esters, methyl ether, cadinene, and a sesquiter-
pene alcohol (melting-point, 138). Characters : Specific
gravity, 0'910 to 0*940 ; optical rotation, -17 to -55;
refractive index (20), 1494 to 1*504; saponification
number, 45 to 100.
Ylang-ylang Oil. The characters of this oil are as
follows: Specific gravity, 0*930 to 0*960; optical rotation,
-38 to -45; refractive index (20), 1-480 to 1*515;
saponification number, 95 to 138 ; soluble in 1 to 2 vols.
95 per cent, alcohol, turbid with more alcohol.
Betulaceae. Sweet Birch or Wintergreen Oil. This is
now produced almost entirely from the bark of Betula
lento, t or sweet birch, which is grown in North America.
The oil, derived from Gaultheria procumbens, which was
formerly used, is practically unobtainable. Artificial
wintergreen oil or methyl salicylate is sold very exten-
sively in place of the natural product. The yield of oil,
which is produced by the action of the ferment " betulase "
on the glucoside " gaultherin " occurring in the bark, is
about 0*5 to 0'7 per cent. It consists practically wholly
of methyl salicylate. Characters: Specific gravity, I'l 80
to 1*187; optically inactive; refractive index, 1*534 to
1*539; boiling-point, 218 to 220; soluble in 6 vols. 70
per cent, alcohol at 25 ; gives deep violet coloration
with ferric chloride in alcohol. See P. & E.O.R., 1914,
60; 1915, 105, 125; 1916, 344, for the detection of
artificial wintergreen oil in the natural product. The
oil derived from Gaultheria procumbens differs from the
SYSTEMATIC SURVEY OF ESSENTIAL OILS 79
Betula lenta oil by having an optical rotation of 25'
to-l.
BurseracesD. Elemi Oil. This is obtained to the
extent of 15 to 30 per cent, by distilling the oleo-resin
of Canarium commune, which grows in the Philippines.
It contains chiefly dipentene and phellandrene. It has a
specific gravity of 0*870 to 0*910, and an optical rotation
of about + 45.
Lignaloe Oil. This is obtained to the extent of 7 to 12
per cent, by distillation of the wood of Bursera delpechiana,
B. cdoexylon, and other species, which are grown chiefly
in Mexico (P. & E.O.E., 1910, 57). It contains principally
linalol (55 to 75 per cent.), geraniol, terpineol and methyl-
heptenone. Characters : Specific gravity, 0*875 to 0*895 ;
optical rotation, 5 to 12; refractive index, 1459 to
1*464; linalol (by acetylation), 55 to 75 per cent. ; soluble
in 2 to 3 vols. 70 per cent, alcohol.
Myrrh Oil. This is derived, the yield varying between
2 to 10 per cent., from the oleo-resin of Commiphora
myrrha, C. cibyssinica, and other species, which grow in
Arabia and Somaliland. The oil contains, according to
its derivation, varying quantities of myrrholic acid, hera-
bolene, metacresol, etc. Characters : Specific gravity,
0*985 to 1*007 ; optical rotation, -67 to -90; refractive
index, about 1*536. Oil of Bisabol Myrrh derived from
the oleo-resin of C. Jcatqf, grown in Somaliland, contains
chiefly bisabolene, which is a sesquiterpene identical with
that contained in lemon and lime oils. Characters :
Specific gravity, 0*883; optical rotation, about -14 20'
(The Volatile Oils, by Gildermeister & Hoffmann (1),
488)
Cannabinacese. Hop Oil. This is distilled to the
extent of 0*3 to 1 per cent, from the flowers (strobiles)
8o FLAVOURING MATERIALS
of Humulus lupulus. The oil is more valuable when the
flowers have not been sulphured. The chief constituents
are dipentene, linalol, tetrahydrocymene, humulene
(identical with a-caryophellene, P. & E.O.R., 1911, 176),
and an olefinic terpene.
Compositse. Arnica Oil. This is obtained by dis-
tilling the flowers and roots of Arnica montana, which
grows in Europe and North America. The oil distilled
from the flowers has a bluish colour when fresh. It
contains a mixture of ethers (phlorone iso-butyric ether,
phlorone dimethyl ether, and thymo - hydroquinone
dimethyl ether). Characters: Specific gravity, O905 to
0-910 (flower oil), 0'990 to 1-000 (root oil); optical
rotation, to -2.
Chamomile Oil. This is distilled to the extent of about
1 per cent, from the freshly dried flowers of Anthemis
nobilis, which is grown in European countries. It has
a blue colour when freshly distilled, which, however,
gradually turns green, then brown. The chief constituents
are amyl alcohol, hexyl alcohol, angelic and tiglic isobutyl
ethers, an alcohol anthemol, an ethylene hydrocarbon
(melting-point, 63), and the blue constituent azulene
(P. & E.O.R., 1915, 46). Characters: Specific gravity,
0-905 to 0-915; optical rotation, -1 to -3; refractive
index at 25, 1'442 to T465 ; soluble in 6 vols. 70 per cent,
alcohol. The German chamomile oil, which is derived
from the flowers of Matricaria chamomilla, contains chiefly
chamomillol, tri-chamomillol, caproic esters, furfuralde-
hyde, umbelliferone methyl ether, and solid hydrocarbons.
It has a specific gravity of 0*930 to 0-940, congeals at
1C. and is soluble in 3 vols. 90 per cent, alcohol.
Tansy Oil. This is distilled to the extent of 01 to 0'2
per cent, from the fresh flowering herb Tanacetum vulgare,
SYSTEMATIC SURVEY OF ESSENTIAL OILS 81
which is grown in European countries and North America.
It contains thujone, borneol and camphor. Characters :
Specific gravity, 0'925 to 0*955 ; optical rotation, +25 to
+ 45 ; soluble in 3 vols. 70 per cent, alcohol.
Tarragon Oil (Estragon Oil). This is distilled from the
flowering herb Artemisia dracunulus, which is grown in
Europe. It contains methyl chavicol, phellandrene, and
para-methoxy-cournarinic aldehyde, and is used in the
preparation of sauces, etc. Characters : Specific gravity,
0'890 to 0-960; optical rotation, + 2 to +9; refractive
index, 1-516 to 1*518; soluble in 10 vols. 80 per cent,
alcohol.
Wormseed Oil. This is distilled to the extent of about
2 per cent, from the flower buds of Artemisia maritima,
which grows in South Kussia and Asia Minor. It con-
tains thujone, cineol, terpinene, dipentene, terpineol and
a sesquiterpene. Characters : Specific gravity, 0*915 to
0-940.
American Wormseed Oil (Chenopodium Oil) is obtained
to the extent of 0'6 to I'O per cent, from the seeds of
Chenopodium ambrosiodes (N.O. Chenopodiacese). This oil
has displaced wormseed oil to a great extent. It contains
60 to 65 per cent, ascaridol, 20 per cent, paracymene and
camphor, sylvestrene, etc. Characters : Specific gravity,
0-950 to 0-990: optical rotation, -5 to -10; refractive
index, 1*466 to 1476; saponification number, 246 to 280;
soluble in 4 to 10 vols. 70 per cent, alcohol (P. & E.O.R.,
1912,16,80; 1913,80; 1915,25,104,125,189; Journ.
Chem. Soc., 1921, i. 259, 797 and 1714).
Wormwood Oil (Absinthe Oil). This is distilled, the
yield being 0*2 to TO per cent., from the herb Artemisia
absinthium, which is grown in Europe and North America.
It contains chiefly thujone, thujyl alcohol, esters (acetic,
6
82 FLAVOURING MATERIALS
palmitic, and iso-valeric), cadinene, phellandrene, and
pinene. Characters : Specific gravity, 0'925 to 0'953 ;
refractive index, 1460 to 1*474
Cruciferse. Mustard Oil. This is derived to the
extent of O'o to O8 per cent, from the seeds of black
mustard, Sinapis nigra. The seeds are pressed and then
macerated with water, under which treatment the enzyme
myrosin acts on the glucoside potassium myronate, both
substances being present in the seeds, with the production
of allyl-iso-thiocyanate. This latter substance is the
chief constituent (92 to 95 per cent.) of mustard oil ;
accompanying it are carbon disulphide and allyl cyanide.
Characters: Specific gravity, 1-014 to 1*032; optical
rotation, nil; refractive index at 25, 1*525 to 1*535.
Geraniacese. Rose Geranium Oils. These are obtained
to the extent of 01 to 0*15 per cent, by distillation of the
leaves of Pelargonium roseum, P. odoratissimum, P. capitum
and other species, which are grown in France, Spain,
Keunion, Algeria, etc. (P. & E.O.R., 1910, 193 ; 1912, 243 ;
1913, 239, 272, 304, 372, 381 ; 1914, 323). The order of
value of the various oils is as follows : Spanish, French,
Algerian and Bourbon. The chief constituents are geraniol,
esters, citronellol, linalol, traces of acetic, butyric, valerianic
and tiglic acids. Among the adulterants which are occa-
sionally used in these oils the following are worthy of
mention: Glycerine acetate, ethyl phthalate, tartrate,
citrate, succinate, oleate, oxalate, geraniol and palma-rosa
oil. Characters : Spanish Specific gravity, 0'889 to
0'898; optical rotation, 10 to 15; refractive index,
1-461 to 1'470; esters (as geranyl tiglate), 35 to 42 per
cent. ; alcohols (as geraniol), 70 per cent. ; soluble in 3
vols. 70 per cent, alcohol. French Specific gravity,
0*895 to 0-905; optical rotation, -7 to -12; refractive
SYSTEMATIC SURVEY OF ESSENTIAL OILS 83
index, 1461 to 1470; esters (as geranyl tiglate), 22 to
28 per cent. ; alcohols (as geraniol), 75 per cent. ; citron-
ellol by formylation, 40 per cent. ; soluble in 3 vols. 70
per cent, alcohol. Algerian Specific gravity, 0*890 to
0*900; optical rotation, 6 to 12; refractive index,
1461 to 1470 ; esters (as geranyl tiglate), 20 to 29 per
cent. ; alcohols (as geraniol), 75 per cent. ; citronellol by
formylation, 33 per cent. ; soluble in 3 vols. 70 per
cent, alcohol. Bourbon Specific gravity, 0*890 to 0*895 ;
optical rotation, 8 to 11; refractive index, 1461 to
1470; esters (as geranyl tiglate), 27 to 34 percent.; total
alcohols (as geraniol), 80 per cent. ; citronellol by formyla-
tion, 44 per cent. ; soluble in 3 vols. 70 per cent, alcohol.
Labiatas. Balm Oil or Melissa Oil. This is distilled
from the fresh green herb Melissa qfficinalis, which is grown
in Europe and North America. Commercial balm oil is
frequently either lemon or citronella oil, or a mixture of
the two, distilled over the green herb. The pure oil is
very expensive and contains chiefly citral, citronellol and
geraniol. Characters: Specific gravity, 0*894 to 0*924;
optical rotation, +0 30' to -6 30'.
Hyssop Oil. This is distilled from the dried flowering
herb Hyssopus officinalis. It is used to some extent in the
compounding of cordials. Its chief constituents are pinene,
a ketone pinocamphone, small quantities of cineol, thujyl
alcohol and thujone. Characters : Specific gravity, 0*925
to 0*940 ; optical rotation, - 19 to - 24 ; soluble in 6 vols.
80 per cent, alcohol.
Lavender Oil. Ordinary lavender oil is obtained to the
extent of 0'5 to 1*0 per cent, by distilling in water the
fresh flowering herb Lavandula vera. The bulk of foreign
oil is derived from the mountainous coastal regions in the
south of France, the better class of oils being obtained from
84 FLAVOURING MATERIALS
the plants grown on the higher slopes. English oils, which
are produced in the neighbourhoods of Mitcham, Hitchin,
Canterbury, etc., are recognised as being the finest in aroma
in the world ; at the same time they only contain 6 to 10
per cent, of esters as compared with 25 to 45 per cent, in
French oils. So that the ester value of lavender oils is no
guide to the comparative values of English and French
oils as many continental authorities claim. The chief
constituents of lavender oil are linalol, nerol, geraniol,
linalyl esters, limouene, cineol, a sesquiterpene and a
trace of pinene (P. & E.O.R., 1916, 50). Characters:
English Specific gravity, 0'883 to 0'890 ; optical rotation,
-5 to -10; refractive index at 25, 1-463 to 1-465; esters
(linalyl acetate), 6 to 10 per cent. ; soluble in 3 vols.
70 per cent, alcohol. French Specific gravity, 0'885 to
0*895; optical rotation, 3 to 9; refractive index at
25, 1-461 to 1-465 ; esters (linalyl acetate), 25 to 45 per
cent. ; soluble in 3 vols. 70 per cent, alcohol. Lavender
oil has been subjected to much scientific adulteration,
especially with synthetic esters of the type of ethyl
phthalate, citrate, tartrate, glycerine acetate, benzyl
benzoate, linalyl acetate, etc.
Spike lavender oil is distilled to the extent of 0*5 to
1 per cent, from the fresh flowering herb Lavandula spica,
which grows in the mountainous coastal regions of France,
Spain and Italy. Its odour is about midway between that
of lavender and rosemary oils. Its chief constituents are
linalol, camphor, borneol, cineol, d-camphene and a sesqui-
terpene. Characters: Specific gravity, 0'905 to 0918;
optical rotation, 2 to +4 (or even up to +6 or +7);
refractive index, 1*462 to T467 ; total alcohols (as borneol),
25 to 45 per cent. ; esters (linalyl acetate), 4 to 6 per cent.;
soluble in 6 vols. 65 per cent, alcohol and in 3 vols. 70 per
SYSTEMATIC SURVEY OF ESSENTIAL OILS 85
cent, alcohol (see P. & KO.R., 1916, 239). This oil is
occasionally adulterated with turpentine.
Marjoram Oil. Oil of sweet marjoram is distilled to the
extent of 0*3 to 0'4 per cent, from the fresh flowering
herb Origanum majorana, which is chiefly grown in Spain.
The chief constituents of the oil are terpineol, terpinene,
terpin hydrate, camphor arid borneol. Characters : Specific
gravity, 0'890 to O'QIO; optical rotation +5 to +18;
refractive index, 1'472 to 1'510 ; soluble in 3 vols. 80 per
cent, alcohol.
Origanum Oils. These are distilled from several species
of Origanum. For example, from Origanum dubium and
0. majoranoides (P. & KO.R, 1918, 70). The oil obtained
from Asia Minor is distilled from 0. Smyrnceum and other
species. The Trentino oil is distilled from 0. hirtum and
0. onites. As might be expected with oils of such varied
derivations the characters have rather wide limits. Char-
acters : Specific gravity, 0*915 to 0*980; optical rotation,
-13 to +3; refractive index, 1'500 to 1-510; phenols,
25 to 85 per cent. ; soluble in 3 vols. 70 per cent, alcohol.
All origanum oils contain principally carvacrol, together
with cymene and sometimes linalol.
Patchouli Oil. This is distilled to the extent of about
2 to 4 per cent, from the leaves of Pogostemon patchouli,
which is grown chiefly in the Straits Settlements, the
West Indies, Penang, Java, Ke*union and Mauritius
(P. & KOE., 1913, 369, 418 ; 1918, 291). Its chief con-
stituents are 40 to 45 per cent, of cadinene, an alcohol
melting at 56 (patchouli alcohol), small quantities of
benzoic and cinnamic aldehydes and other bodies. Char-
acters : Specific gravity, 0'950 to 0-995 ; optical rotation,
-40 to -68; refractive index, 1-504 to 1-520; saponi-
fication number, 4 to 18 ; saponification number (after
86 FLAVOURING MATERIALS
acetylation), 35 to 80 ; soluble in 5 to 6 vols. 90 per cent,
alcohol.
Peppermint Oils. These are obtained by steam distilla-
tion of one or two species of Mentha. The English oil is
derived from " black " and " white " Mentha piperita, the
white variety being superior in quality (P. & E.O.E., 1910,
6; 1911, 175). The following are the characters of the
English oil: Specific gravity, 0-900 to 0-910; optical
rotation, -22 to -33; refractive index, 1-460 to 1465;
total menthol, 55 to 70 per cent.; esters (as menthyl
acetate), 3 to 15 per cent, ("black" oil usually contains
7 to 10 per cent, esters and the " white " oil 11 to 15 per
cent.); soluble in 3 to 4 vols. of 70 per cent, alcohol.
Most peppermint oils improve with storing for a period.
The oils have a very widespread use both as flavouring
agents and in pharmacy.
American peppermint oil is derived from Mentha
piperita, which is grown chiefly in Wayne County,
Kalamazoo, etc. (P. & KO.R, 1910, 7; 1917, 60). It
differs from English oil in that it usually contains a lower
percentage of esters. The following are the characters of
American peppermint oil : Specific gravity, 0"900 to 0'920 ;
optical rotation, 18 to 33 ; refractive index, 1'458 to
1-467 ; total menthol, 50 to 65 per cent. ; esters (as menthyl
acetate), 6 to 10 per cent. ; soluble in 3 to 4 vols. 70 per
cent, alcohol when double-distilled, otherwise it usually
gives a cloudy solution in these proportions.
Japanese peppermint oil is derived from Mentha arvensis
(P. & E.O.R, 1911, 7 ; 1918, 32). It has a very woody
taste, and is used chiefly as a source of menthol, which
it contains to the extent of 70 to 90 per cent. The
dementholised Japanese peppermint oil on the market
usually contains 40 to 45 per cent, menthol. A rectified
SYSTEMATIC SURVEY OF ESSENTIAL OILS 87
dementholised Japanese peppermint oil has been offered
on the market during the last few years, the woody flavour
having been eliminated to an extent which permits the
use of the oil for blending purposes. The following
are the characters of Japanese peppermint oil : Specific
gravity, 0-900 to 0'915; optical rotation, -30 to -42;
refractive index, 1462 to 1468 ; total menthol, 70 to 90
per cent. ; esters (as menthyl acetate), 3 to 6 per cent. ;
soluble in 3 to 4 vols. 70 per cent, alcohol (P. & E.O.R.,
1918, 207).
The chief constituents of peppermint oils of all deriva-
tions are menthol, menthyl acetate, valerianate, etc.,
menthone, phellandrene, pinene, limonene, cadinene,
cineol and traces of dimethyl sulphide, aldehydes and
acids. Adulteration by means of copaiba oil, gurjiih
balsam, cedar oil, etc., may be determined by fraction-
ation ; glycerine acetate can be extracted with water or
5 per cent, alcohol.
Rosemary Oil. This is distilled to the extent of 1 to 2
per cent, from the dried leaves of Rosmarinus officinalis,
which is grown chiefly in Spain, Northern Africa
(P. & E.O.R., 1916, 214), Italy and France. The French
oil is considered to be of superior quality (P. & E.O.R.,
1910, 190; 1911, 109, 274). The chief constituents of
the oil are pinene, cineol, camphor, borneol, camphene
and bornyl acetate. Adulteration is sometimes practised
with camphor oil. Characters : Specific gravity, 0'895 to
0-920 ; optical rotation, - 3 to + 1 (or even up to + 1 5) ;
refractive index at 25, 1465 to 1475 ; total alcohols, as
borneol, 10 to 18 per cent. ; esters, as bornyl acetate,
2 to 6 per cent. ; soluble in 10 vols. 80 per cent, alcohol.
Sage Oil This is distilled to the extent of 1-25 to 2*5
per cent, from the fresh flowering herb, Salvia officinalis,
88 FLAVOURING MATERIALS
which grows in Mediterranean countries (P. & E.O.R.,
1916, 369). It contains chiefly cineol, pinene, borneol
and thujone. Characters : Specific gravity, 0'910 to
0*930 ; optical rotation, +10 to +25; refractive index,
1*462 to 1467 ; esters, 2 to 6 per cent. ; total alcohols,
20 to 25 per cent. ; thujone, 40 to 50 per cent. ; soluble
in 3 vols. 70 per cent, alcohol. Other oils of sage are
derived from Salvia triloba (Spanish sage) and S. sclarea
(Muscatel or " clary " sage). The former has a specific
gravity of 0*925 to 0*932 ; optical rotation, + 13 to + 19 ;
total esters (as linalyl acetate), 9 to 21 per cent. ; total
alcohols, 23 to 29 per cent. ; soluble in 6 vols. of 70 per
cent, alcohol. The latter has a specific gravity of 0*907
to 0*928 ; optical rotation, - 19 to - 24 ; and a content of
40 to 50 per cent, linalyl acetate. It possesses an odour
resembling lavender.
Spearmint Oil. This oil is distilled to the extent of
0*2 to 0*3 per cent, from the fresh green herb Mentha
viridis (American spearmint), and also from M. crispa
(German spearmint). Its chief constituents are carvone,
pinene, limonene and traces of esters. Characters :
Specific gravity, '0*920 to 0*940 ; optical rotation, -30 to
-52; refractive index at 25, 1*481 to 1*487; carvone,
50 to 60 per cent. ; soluble in an equal volume of 90 per
cent, alcohol, goes turbid with more alcohol.
Thyme Oils. Eed thyme oil is obtained to the extent
of 0*3 to 2*6 per cent, by distillation from the fresh and
dried herb Tliymus vulgaris, which is grown in
Mediterranean countries. It contains chiefly carvacrol,
thymol, cymene, pinene, linalol and borneol. Characters :
Specific gravity, 0*905 to 0*935 ; optical rotation, to 4 ;
refractive index, 1*485 to 1*498; phenols, 20 to 50 per
cent. ; soluble in 3 vols. 80 per cent, alcohol,
SYSTEMATIC SURVEY OF ESSENTIAL OILS 89
Lemon thyme oil (Spanish) is distilled from the flower-
ing herb Thymus hyemalis. It contains citral in addition
to carvacrol. Characters: Specific gravity, 0-900 to
0-920; citral, 10 to 20 per cent.; phenols, 8 to 12 per
cent, (see also P. & E.O.R., 1912, 212; 1915, 187).
Wild thyme oil is derived to the extent of 015 to 0'6
per cent, from Thymus serpyllum, which grows in Europe,
North America and Asia. It contains chiefly cymene
and terpenes, together with a trace of phenols. Char-
acters : Specific gravity, 0'890 to 0*920 ; optical rotation,
10 to 21. For oil of Thymus mastichina or wood
marjoram, see P. & E.O.R., 1911, 40 ; 1915, 187.
Lauraceae. Bois de Rose Oil (Male). This is distilled
from Ocotea caudata, which is grown in French Guiana.
The oil is similar in composition and odour to linaloe
oil. The " femelle " oil is obtained from Protium altissi-
mum and contains geraniol, nerol, terpineol, inethyl-
heptenone, etc. Characters : Specific gravity, 0'870 to
0-880; optical rotation, 15 to 17; soluble in 3 vols.
70 per cent, alcohol.
Camphor Oil is obtained by distillation of the wood of
Cinnamomum camphora, which grows chiefly in Formosa,
Japan and China. The process is subsidiary to the
manufacture of camphor. Two oils are obtained during
the distillation, namely, " light " and " heavy." The light
oils contain chiefly terpenes, e.g. pinene, limonene, phellan-
drene, dipentene, terpineol, cineol, borneol and camphor.
The heavy oils contain safrol, eugenol, camphor and
cadinene. Characters : Light Oil Specific gravity, 0'860
to 0-950; optical rotation, +12 to +32; refractive
index, 1*465 to 1-481. Heavy oil 0'950 to 1-100;
optical rotation, to +12; refractive index, 1*500 to
1-508,
90 FLAVOURING MATERIALS
Cassia Oil. This is distilled to the extent of 0*5 to 2
per cent, from the bark, leaves and twigs of Cinnamomum
cassia, which is grown chiefly in China. The chief con-
stituents are 70 to 90 per cent, of cinnamic aldehyde,
cinnamic esters, terpenes, salicylic aldehyde, coumarin
(P. & E.O.R., 1916, 7), and phenylpropyl-acetate. Char-
acters : Specific gravity, 1*050 to 1*065 ; optical rotation,
1 to +1 ; refractive index, 1*585 to 1*605; soluble in
3 to 4 vols. of 70 per cent, alcohol. The chief adulterants
are resin and mineral and fatty oils. The former
particularly has a very extensive use in this respect,
although improvement has been made of late years
(P. & E.O.R., 1916, 323). Lead, derived from the con-
tainers in which the oil is shipped, must also be looked
for in the oil.
Cinnamon Oil. This is distilled to the extent of 0*5 to
1 per cent, from the bark of Cinnamomum zelanicum,
which is grown chiefly in Ceylon. The oil contains 55
to 75 per cent, of cinnamic aldehyde, together with
pinene, cymene, phellaudrene, cuminic aldehyde, benzalde-
hyde, nonaldehyde, methyl-amyl-ketone and a small
quantity of eugenol. Characters: Specific gravity,
l/OOO to 1*040; optical rotation, to 1; refractive
index at 25, 1*565 to 1*590 ; soluble in 3 vols. of 70 per
cent, alcohol (see P. & E.O.R., 1910, 169).
The oil distilled from the leaves contains 75 to 90 per
cent, eugeuol and also a quantity of safrol. Its cinnamic
aldehyde content is very small. Characters : Specific
gravity, 1*045 to 1*065 ; optical rotation, -1 to +1; re-
fractive index at 25, 1*530 to 1*540 ; soluble in 3 vols.
70 per cent, alcohol.
The oil distilled from the roots contains eugenol,
camphor, safrol, benzaldehyde, benzoic esters, etc.
SYSTEMATIC SURVEY OF ESSENTIAL OILS 91
Laurel Oil. This is distilled to the extent of 1 to 3
per cent, from the leaves of Laurus nobilis, which is
cultivated in Mediterranean countries. It has an odour
resembling cajuput oil and contains chiefly cineol,
geraniol, eugenol, pinene, methyl-chavicol, esters, a
sesquiterpene and a sesquiterpene alcohol. Characters :
Specific gravity, O920 to 0-936 ; optical rotation, - 15 to
18; ester value, 47 ; cineol, 25 to 50 per cent. ; soluble
in 3 vols. 80 per cent, alcohol.
Shiu Oil. This is obtained from Japan and is chiefly
interesting because of its high content of linalol
(P. & E.O.R, 1912, 111, 124, 239). Characters : Specific
gravity, 0-870 to 0'883; optical rotation, -14 to -16;
refractive index, about 14606 ; total alcohols by acetyla-
tion, 47 to 62 per cent. Another interesting Japanese
oil is " Kuromoji," which is obtained from the leaves and
twigs of Lindera sericea (P. & KO.R, 1912, 263). This oil
contains 40 to 50 per cent, linalol, 10 per cent, esters
(as geranyl acetate), terpineol, 1-carvone, dipentene and
d-limonene. Its odour resembles that of coriander oil.
Characters : Specific gravity, 0*890 to 0'915 ; optical
rotation, 2 to 14; soluble in 4 vols. 70 per cent,
alcohol.
Sassafras Oil. This is distilled to the extent of 3 to 9
per cent, from the root-bark of the smaller roots of
Sassafras officinale, which is grown extensively in North
America. Its chief constituent is 80 to 90 per cent,
safrol, other constituents being pinene, camphor, phellan-
drene, cadinene and eugenol. Its most common adulterant
is camphor oil (which see). Characters : Specific gravity,
1-065 to 1-095; optical rotation, +1 to +4 ; refractive
index, 1/523 to T530 ; soluble in 2 vols. 90 per cent,
alcohol.
92 FLAVOURING MATERIALS
Leguminosse. Copaiba Oil This is derived, the yield
being about 40 to 65 per cent., from the balsam or oleo-
resin of Copaifera Langsdorffii and other species, which are
grown in the northern coastal sections of South America.
The constituents are chiefly sesquiterpenes (caryo-
phyllene). Characters: Specific gravity, 0'895 to 0918 ;
optical rotation, 7 to 25; refractive index at 25,
1493 to 1-500.
Mag noliacese. Star Anise Oil. This is obtained to the
extent of about 3 per cent, from the fruit of Illicium
.verum, which grows in Southern China and Tonkin. The
chief constituents of the oil are 80 to 90 per cent, anethol,
d-pinene, 1-phellandrene, para-cymene, anisic aldehyde,
anisic acid, methyl-chavicol, safrol, terpineol, cineol and a
sesquiterpene. Characters : Specific gravity (20/15),
0-975 to 0-990; optical rotation, -2 to +1; refractive
index at 25, 1*551 to 1'558; melting-point after solidifica-
tion, 17 to 19 ; soluble in 3 vols. 90 per cent, alcohol.
Japanese star anise oil derived from Illicium religiosum
contains eugenol, safrol and limonene ; its specific gravity
is about 1*006, and its optical rotation about 8.
Malvaceae. Oil of Ambrctte. This is derived, the yield
being about 0*2 per cent., from the seeds of Hibiscus
abelmoschus, which is grown in Java and Martinique.
The oil has a musk-like odour, is solid at ordinary
temperatures and contains palmitic acid. Characters :
Specific gravity, about O900 ; optical rotation, nil or very
slightly dextro ; melting-point, 30 to 35 ; saponification
number, 180 to 200.
Myristicacese. Nutmeg Oil. This is distilled to the
extent of 7 to 14 per cent, from the seeds of Myristica
fragrans, which grows in the Moluccas and especially in
the Banda and Sunda Islands. Characters: Specific
SYSTEMATIC SURVEY OF ESSENTIAL OILS 93
gravity, 0-865 to 0*930 ; optical rotation, +10 to +30;
refractive index at 25, 1-475 to 1-484; soluble in 3 vols.
90 per cent, alcohol.
Mace Oil This is distilled from the arillus enclosing
the seeds of Myristica fragrans. It contains chiefly
myristicol, which is a mixture of geraniol, terpineol,
linalol and borneol, and also 4 per cent, of myristicin,
iso-myristicin, myristic acid, safrol, pinene, dipentene,
camphene and small quantities of eugenol and iso-eugenol.
Characters: Specific gravity, 0'890 to 0'930; optical
rotation, +10 to +20; refractive index at 25, 1*476 to
1480 ; soluble in 3 vols. 90 per cent, alcohol.
Myrtaceae. Bay Leaf Oil. This is obtained to the
extent of 2 to 3 per cent, by distillation of the leaves of
Pimenta acris, which is grown in the West Indies
(P. & E.O.R., 1914, 425 ; 1916, 34). The chief constitu-
ents are eugenol, methyl-eugenol, phellandrene, an olefinic
terpene myrcene, and also traces of citral, chavicol and
methyl-chavicol. Characters : Specific gravity, 0*950 to
0-990 optical rotation, to 2; phenols (eugenol), 50 to
75 per cent. ; refractive index, 1*510 to 1*520 (see
P. & E.O.R., 1915, 33; 1916, 295).
Cajuput Oil. This is distilled from the leaves and twigs
of Melaleuca leucadendron, var. lancifolia or M. minor,
which grows in India, the East Indies and Australia
(P. & E.O.R., 1910, 121 ; 1911, 146 ; 1912, 243). The
chief constituents are cineol (45 to 55 per cent.), pinene,
terpineol and small quantities of benzaldehyde and valeric
aldehyde. Characters: Specific gravity, 0*919 to 0930;
optical rotation, to 4; refractive index at 25, 1*460
to 1*470; cineol, 45 to 55 per cent.; soluble in 3 vols.
80 per cent, alcohol.
Glove Oil. This is distilled to the extent of 15 to 19
94 FLAVOURING MATERIALS
per cent, from the dried flower-buds of Eugenia caryo-
phyllata, grown in Zanzibar, Penang, Madagascar,Mauritius,
Seychelles, the West Indies, the Moluccas, etc. (P. & E.O.R.,
1917, 308). The chief constituents are eugenol (85 to 95
per cent.), esters, furfural, caryophyllene, methyl alcohol,
also minute traces of amyl-methyl-ketone and methyl
benzoate. Characters: Specific gravity, T047 to T065
(this increases with exposure to light and air, see
P. & E.O.R., 1910, 243); optical rotation, to -2;
refractive index at 25, 1-528 to 1'540 ; phenols
(eugenol), 85 to 95 per cent.; soluble in 3 vols. 70
per cent, alcohol.
Eucalyptus Oil. This is distilled to the extent of 0'8 to
1-5 per cent, from the dried leaves of several species of
Eucalyptus, Q.g.Eucalyptusglobulus,E. polylractea, E. dumosa
and JE. oleosa (P. & E.O.R., 1913, 281; 1914, 22; 1915,
181), which are grown in Australia, New Zealand,
California, Spain and Algeria. The chief constituents are
cineol, phellandrene, pinene, cymene, piperitone, aroma-
dendral, a sesquiterpene aromadendrene, eudesmic esters,
eudesmol (melting-point, 79 to 80), also traces of aldehyde,
e.g. butyric, caproic and valeric, and amyl alcohol. Other
eucalyptus oils are derived from E. macarthuri, E. aggregata
and E. staigeriana. The first of these contains 60 to 75
per cent, of geraniol principally as geranyl acetate, the
second contains upwards of 50 per cent, amyl eudesmate
and the last contains 1-limonene and citral. Oil of E.
citriodora contains no cineol, the chief constituent being
citronellal together with esters. Oil of Backhousia citriodora
is composed almost wholly of citral (P. & E.O.R., 1912,
241 ; 1915, 92, 182). Oil of E. amygdalina is composed
largely of phellandrene. Characters of Eucalyptus oils :
Medicinal Oil (globulus) Specific gravity, 0-910 to 0'930 ;
SYSTEMATIC SURVEY OF ESSENTIAL OILS 95
optical rotation, 10 to +10; refractive index at 25,
1459 to 1470; cineol, 55 to 80 per cent. ; soluble in 3 to
10 vols. 70 per cent, alcohol. Amygdalina Oil Specific
gravity, 0'885 to 0'890; optical rotation, -25 to -80;
refractive index, 1475 to 1485 ; cineol, 5 to 25 per cent.
Citriodora Oil Specific gravity, 0'865 to 0'905 ; optical
rotation, to +2; refractive index, 1455 to 1460;
citronellal, 80 to 95 per cent. ; soluble in 4 to 5 vols.
80 per cent, alcohol. Oil of Backhousia Citriodora
Specific gravity, 0'895 to 0'900; refractive index, 14889;
citral, 90 to 95 per cent. ; soluble in 3 vols. 70 per cent,
alcohol (see P. & E.O.R., 1918, 249).
Pimento Oil. This is obtained to the extent of 3 to 4'5
per cent, from the unripe fruit of Pimenta officinalis,
which is grown in the West Indies. The chief constituents
are eugenol, the methyl ether of eugenol, 1-phellandrene,
caryophyllene, cineol, palmitic acid and resin. Characters :
Specific gravity, 1040 to 1*055 ; optical rotation, to
4; refractive index at 25, V508 to 1'535; phenols
(eugenol), 60 to 75 per cent. ; soluble in 2 vols. 70 per
cent, alcohol.
Oleaceae. Jasmine Oil. This is obtained by extraction
of pomade, made by the enfleurage process (see later
section), with acetone (P. & E.O.R., 1916, 36). Jasminium
grandiflorum is usually the species used in the South of
France for the preparation of the pomade. The com-
position of jasmine oil is roughly as follows : Benzyl
acetate, 65 per cent. ; linalol, 16 per cent. ; linalyl
acetate, 7 '5 per cent. ; benzyl alcohol, 6 per cent. ; to-
gether with small quantities of geraniol, methyl an-
thranilate, para-cresol, indol and a ketone "jasmone."
Characters : Specific gravity, 1*006 to 1'018 ; optical
rotation, +2 30' to +3 30'; esters (as linalyl acetate),
96 FLAVOURING MATERIALS
90'3 to 954 per cent. ; esters (as benzyl acetate), 69*1 to
73-0 per cent.
Piperaceaa. Gubeb Oil. This is distilled in steam to
the extent of 10 to 18 per cent, from the dried, unripe
fruit of Piper cubeba, which is grown chiefly in Java. It
is used in the compounding of certain liqueurs. Its chief
constituents are 1-pinene, camphene, dipenteue, cadinene
and cubeb camphor (melting-point, 68 to 70). Char-
acters: Specific gravity, 0910 to 0'930 ; optical rotation,
-25 to -40; refractive index at 25, 1485 to 1-502;
soluble in 3 to 10 vols. 90 per cent, alcohol.
Pepper Oil. This is distilled from the unripe berries of
Piper nigrum. It contains chiefly phellandrene and
sesquiterpenes. Characters : Specific gravity, 0'870 to
0'905: optical rotation, 5 to +2.
Rosaceae. Bitter Almond Oil. This is distilled, with
a yield of 0'5 to 1/0 per cent., from the seeds of Prunus
amygdalus amara, after the same have been pressed and
macerated with water. Essential oil of apricot and peach
kernels is similar in composition to oil of bitter almonds.
The essential oil is produced during the maceration process
by the action of the enzyme emulsin on the glucoside
amygdalin. The chief constituents of the oil are benzal-
dehyde, hydrocyanic acid and mandelic nitrile. Charac-
ters : Specific gravity, T045 to 1*060; optical rotation,
nil; refractive index, T542 to 1'556 ; soluble in 2 vols.
70 per cent, alcohol. The oil is also sold "free from
prussic acid." It is deprived of this body by treat-
ment with ferrous sulphate and lime and redistilling
(P. & E.O.R., 1916, 276).
Cherry Laurel Oil. This oil, which is very similar to
bitter almond oil, is distilled from the leaves of Prunus
laurocerasus, which is grown in Italy, Switzerland,
SYSTEMATIC SURVEY OF ESSENTIAL OILS 97
Germany, etc. Its chief constituents are benzaldehyde,
prussic acid and a trace of benzyl alcohol. Characters:
Specific gravity, 1*050 to T065 ; optical rotation, nil.
Otto of Rose. The Bulgarian otto is derived from the
fresh blooms of Rosa damascena, which grows on the
Balkan hillsides (P. & E.O.R., 1916, 11, 39; 1918, 277).
The chief constituents are citronellol, geraniol, nerol,
phenyl-ethyl-alcohol, farnesol and about 10 to 15 per
cent, of stearoptene, consisting of mixed paraffin hydro-
carbons (melting-point, 34). Characters : Specific gravity,
(30/15), 0-851 to 0-862; optical rotation at 25, -2 to
-4; refractive index at 25, 1460 to 1465; melting-
point, 18 to 22 ; total alcohols by acetylation (as geraniol),
65 to 75 per cent. ; citronellol by formylation, 30 to 38
per cent. Otto of rose which has been deprived of its
stearoptene has characters as follows: Specific gravity,
0-882 to 0-885; optical rotation, -3 to -5; refractive
index at 25, 1466 to 1468; total alcohols, 80 to 85 per
cent. ; citronellol, 40 to 45 per cent.
The use of French otto of rose has been gaining ground
during the last few years. This otto is produced from
various types of roses, e.g. Eose de Mai, Ulrich Brunner,
Paul Nabonand, etc., so that the proportion of constituents
and also the characters vary considerably, a fact which
is an advantage in that varying shades of rose odours can
be produced. The following are, however, the characters
given by one of the leading producers as average repre-
sentative figures : Specific gravity at 30, 0'864 ; optical
rotation, 1 to 4 ; ester value, 12 to 32 ; melting-point,
20 to 28 ; total alcohols, 70 to 80 per cent. ; geraniol,
about 32 per cent. ; citronellol, variable (see also
P. & E.O.R., 1917, 6, 220, 279, 330; 1918, 163, 168).
Wild Cherry Bark Oil. This is distilled to the extent
7
98 FLAVOURING MATERIALS
of about 0'2 per cent, from the bark of Prunus mrginiana.
It resembles oil of bitter almonds both as regards con-
stituents and characters.
Rutacese. Bergamot Oil. This is obtained by pressure
from the fresh peel of the fruit of Citrus bergamia, which
is grown in Southern Italy. The oil produced by distilla-
tion processes is of a distinctly inferior quality. The oil
contains limonene, pinene, octylene, linalyl acetate, linalol,
dipentene, camphene, dihydrocuminol, terpineol, limene
(bisabolene) and bergaptene (a stearoptene melting at
188). Characters: Specific gravity, 0'881 to O887 ;
optical rotation, +8 to +20; refractive index, 1460 to
T469 ; esters (as linalyl acetate), 35 to 40 per cent.; non-
volatile residue, 5 to 6 per cent.
BucTiu Oil. This is distilled to the extent of 1 to 2 per
cent, from the leaves of Barosma betulina, B. crenulata and
B. serratifolia, which grow in South Africa. The chief
constituents are diosphenol (a crystalline phenol melting
at 81 and boiling at 232), menthone, limonene and
dipentene. Characters : Specific gravity, 0'935 to 0'945
(betulina oil), 0'945 to 0'960 (serratifolia oil).
Citron or Cedrat Oil. This oil is obtained from the peel
of the Citrus medica. Mixtures of lemon, orange and
bergamot oils are occasionally offered on the market as
citron oils. The chief constituents are citral, limonene,
dipentene and a crystalline body which melts at 144 to
145. The oil is not much used in commerce. Characters :
Specific gravity, 0'850 to 0'870 ; optical rotation, +65 to
+ 80; refractive index, about 1*475; citral, 5 to 7 percent.
Lemon Oil. This is obtained from the fresh peel of
Citrus limonum, which is cultivated chiefly in Sicily,
Southern Italy, France and Spain. A new process for
the recovery of the oil from the peel is mentioned in the
SYSTEMATIC SURVEY OF ESSENTIAL OILS 99
P. & E.O.R., 1915, 91. The chief constituents of the oil
are citral, limonene, phellandrene, 1- and d-pinene, limene
(bisabolene), geraniol, linalol, esters, aldehydes (nonylic,
octylic and decylic) and citraptene (melting-point, 143).
Characters : Specific gravity, 0'857 to 0*862 ; optical rota-
tion, + 57 to +65; refractive index at 25, 1473 to
1476 ; citral, 3*5 to 5 per cent.
Limes Oil. .The hand-pressed variety is obtained from
the fruit of Citrus limetta, which grows in Italy, the dis-
tilled variety being obtained from Citrus medico, var. acida,
which is cultivated in the West Indies. The two oils
differ in both composition and characters. The constituents
of the hand-pressed oil are as follows : Citral (6 to 10 per
cent.), limonene, dipentene, pinene, linalol, linalyl acetate
and a stearoptene. Its characters are : Specific gravity,
0-872 to 0-885; optical rotation, +35 to +40; refractive
index, 1476 to 1485. The distilled oil contains chiefly
limonene, pinene, dipentene, cymene and limene, but
no citral. Its characters are: Specific gravity, 0*856 to
0-868; optical rotation, +34 to +54; refractive index,
1470 to 1478.
Neroli Oil. The " Bigarade " oil is obtained from the
fresh flowers of the bitter orange. The " Portugal " variety
is obtained from the flowers of the sweet orange. Both
oils are produced chiefly in the South of France, also to
some extent in Spain (P. & E.O.R., 1913, 137, 375). The
chief constituents of neroli oil are nerol, linalol and geraniol
and their esters, terpineol, limonene, pinene, camphene,
dipentene, jasmone, methyl-anthranilate, stearoptene and a
a trace of indol. Characters : Specific gravity, 0*870 to
0-885 ; optical rotation, to + 5 ; refractive index, 1468 to
1477 ; esters (as linalyl acetate), 7 to 20 per cent. ; soluble
in 3 vols. 80 per cent, alcohol.
ioo FLAVOURING MATERIALS
Orange Oil. This is obtained from the fresh peel of
Citrus aurantium and G. bigaradia, the former being the
sweet orange oil of commerce and the latter the bitter
orange oil The chief constituents are limonene, terpineol,
methyl-anthranilate, linalol, citraptene and less than 1 per
cent, of aldehydes (citral, decylic aldehyde, etc.). Charac-
ters : Bitter Orange Oil Specific gravity, 0'848 to 0'853 ;
optical rotation, +91 to +98; refractive index, 1'472 to
1-478. Sweet Orange Oil Specific gravity, 0'846 to
0-852; optical rotation, +96 to +99; refractive index,
1-472 to 1'478. The variety known as Mandarin Oil,
which is derived from C. Madurensis, contains chiefly
limonene, and has the following characters : Specific
gravity, 0-855 to 0*859; optical rotation, +65 to +75.
Petitgrain Oil. This is derived from the leaves and
young shoots of the bitter and sweet orange, the former
being known as " Bigarade." An inferior grade is pro-
duced in Paraguay, the best oils being obtained from
France, Spain and Italy. The chief constituents are
linalol and geraniol and their esters, limonene, sesquiter-
penes and stearoptene. Paraguay petitgrain oil contains
pinene, camphene, dipentene, terpineol and esters of
geraniol. The characters of the two types of oil are as
follows: Continental Specific gravity, 0'885 to 0'900 ;
optical rotation, 5 to +3; refractive index, 1-462 to
1'465 ; esters (as linalyl acetate), 50 to 80 per cent. ;
soluble in 3 vols. 70 per cent, alcohol. Paraguay
Specific gravity, 0-884 to 0*895 ; optical rotation, 2 to
+ 5; refractive index, 1-462 to 1-465; esters (as linalyl
acetate), 35 to 65 per cent. ; soluble in 2 to 3 vols. 80 per
cent, alcohol.
SantalaceaB. Sandalwood Oil. This is distilled, using
high-pressure steam, from the wood of Santalum album,
SYSTEMATIC SURVEY OF ESSENTIAL OTL aca
the yield being 2 to 6 per cent. The trees are grown
chiefly in India (P. & E.O.R., 1918, 18, 182) and an
inferior oil is produced by the natives using open fire
stills. Sandalwood oils of other derivations are described
in P. & E.O.R., 1911, 11, 79; 1913, 163. The chief con-
stituents are 90 to 97 per cent, of santalol (Pharm.
Journ., ii./08, 624; Chem. & Drug., ii./09, 581), which is a
mixture of sesquiterpene alcohols, the aldehyde santalal,
two sesquiterpenes a- and /3-santalene and santene (P. &
E.O.R., 1910, 192). Characters: Specific gravity, 0'973
to 0'985 ; optical rotation, 13 to 21 ; refractive index
at 25, 1-500 to 1*510 ; saponification number, 5 to 15 ;
soluble in 6 vols. 70 per cent, alcohol (see P. & E.O.R.,
1916,47, 116, 210, 254, 278; Am. Journ. Pharm., 1911,
335).
Umbelliferae. Ajowan Oil This is distilled to the
extent of 3 to 4 per cent, from the fruits of Carum ajowan
and C. copticum, which are grown in India, Persia,
Afghanistan and Egypt. The thymol of commerce is
obtained chiefly from ajowan oil. The chief constituents
are thymol, which crystallises out on cooling, cymene and
terpinene. Characters : Specific gravity, 0'900 to 0'930 ;
optical rotation, +1 to +2; thymol 40 to 55 per cent.
soluble in 3 vols. 70 per cent, alcohol.
Angelica Oil. This is distilled to the extent of 0'3 to
1*0 per cent, from the dried root, leaves and stems of
Angelica archangelica, which is grown in Greenland,
Eussia and Siberia. It contains pinene, phellandrene,
cymene, oxymyristmic acid, oxy-penta-decylic acid,
valerianic acid and a crystalline lactone melting at 83.
Characters: Specific gravity, 0'857 to 0*918; optical
rotation, +16 to +32; refractive index, 1479 to 1482.
Anise Oil. This is distilled to the extent of 1*5 to 6*0
;: FLAVOURING MATERIALS
per cent, from the fruits of Pimpinella anisum, which is
grown in France, Holland, Germany, Eussia, etc. Its
chief constituents are 80 to 90 per cent, of anethol,
together with methyl-chavicol. Characters: Specific
gravity (20/15), 0'975 to 0*990 ; optical rotation, to
2; melting-point, 15 to 19; soluble in 3 to 5 vols.
90 per cent, alcohol (P. & E.O.R., 1916, 59). It is some-
times adulterated with fennel oil (see later). As the oil
ages its specific gravity and solubility increase owing to
the formation of oxidation products.
Caraway Oil. This is distilled to the extent of 4 to 7
per cent, from the ripe fruit of Carum carvi, which is
cultivated in Europe and Asia. It contains chiefly
carvone and limonene. Characters : Specific gravity,
0-907 to 0-920 (the B.P. requires the specific gravity to be
not under 0'910); optical rotation, +70 to +82; refrac-
tive index at 25, 1'485 to 1'497 ; carvone, 50 to 60 per-
cent. ; soluble in 10 vols. 80 per cent, alcohol.
Celery Oil This is distilled to the extent of 2'5 to 3'0
per cent, from the fruit of Apium graveolens, which is
largely cultivated in European countries. The chief
constituents are about 90 per cent, of terpenes, consisting
of limonene, together with a sesquiterpene, selinene, and
traces of guaiacol, a phenol melting at 66 to 67,
sedanolid (a lactone), sedanolic acid, sedanonic anhydride
and palmitic acid. Characters : Specific gravity, 0'870 to
0*895; optical rotation, +67 to +79; refractive index,
1-479 to 1-481 ; soluble in 10 vols. 90 per cent, alcohol.
Coriander Oil. This is distilled to the extent of 0'4 to
1/0 per cent, from the ripe fruits of Coriandrum sativum,
which is grown in France, Italy, Holland and Kussia
(P. & E.O.E., 1918, 70). The known constituents of the
oil are d-linalol and d-pinene. Characters: Specific
SYSTEMATIC SURVEY OF ESSENTIAL OILS 103
gravity, 0'870 to O885 ; optical rotation, +8 to +14*;
refractive index at 25, 1463 to 1467; alcohols by
acetylation, 45 to 55 per cent. ; soluble in 3 vols. 70 per
cent, alcohol.
Cummin Oil. This is distilled to the extent of 2*5
to 4*0 per cent, from the fruits of Cummin cyminum,
which is grown in Malta, Egypt, Morocco, Syria, India,
the East Indies, etc. (P. & E.O.R., 1918, 70). It is also
known as Eoman caraway oil and contains cuminic
aldehyde, cymene and a terpene which boils at 156 (P. &
E.O.R., 1913, 43). Characters : Specific gravity, 0'893 to
0*930; optical rotation, +4 to +8; refractive index,
1-497 to 1-509; cuminic aldehyde, 20 to 30 per cent.;
soluble in 3 to 10 vols. 80 per cent, alcohol.
Dill Oil. This is obtained to the extent of 3 to 4 per
per cent, by distilling the fruit of Peucedanum graveolens,
which is cultivated in England, Germany, the Balkans,
etc. It contains 40 to 60 per cent, of carvone, also
phellandrene and limonene. Characters : Specific gravity,
0-895 to 0-915; optical rotation, +70 to +80; refractive
index at 25, 1'477 to 1488 ; soluble in 5 to 8 vols. 80 per
cent, alcohol and in 3 vols. 90 per cent, alcohol (P. &
E.O.R., 1917, 349).
Fennel Oil. This is distilled, with a yield of 4 to 6 per
cent., from the fruits of Foeniculum vulgar 'e, which is
cultivated in France, Italy, Germany, India, Japan, etc.
It contains 50 to 60 per cent, anethol, also fenchone,
dipentene and d-pinene. Characters: Specific gravity,
0-960 to 0-990; optical rotation, +6 to +24; refractive
index, T525 to 1*550 ; melting-point (after solidification),
3 to 6 ; soluble in 5 to 8 vols. 80 per cent, alcohol.
Parsley Oil. This is distilled to the extent of 2 to 6
per cent, from the fruit of Petroselinum sativum, which
104 FLAVOURING MATERIALS
grows in many countries of moderate climate. The chief
constituents are apiol and terpenes. Characters : Specific
gravity, 1-050 to 1100; optical rotation, -5 to -10;
refractive index, 1488 to 1 519.
Verbenaceae. Verbena Oil. This is distilled from
Verbena offi.cinalis and V. triphylla. It is largely sub-
stituted in commerce by lemon-grass oil, which resembles
it to some extent. The chief constituents of the oil are
citral, limonene, a stearoptene, a sesquiterpene and
geraniol. Characters : Specific gravity, 0*900 to 0'92u ;
optical rotation, 8 to 16; citral, 20 to 38 per cent.;
soluble in 3 vols. 80 per cent, alcohol. An oil derived from
Aloysia citriodora or Lippia citriodora is termed Spanish
Verbena oil (P. & E.O.R., 1915, 185).
CHAPTEE VII
TEEPENELESS AND SESQUITEEPENELESS OILS
THE production of concentrated essential oils by the
elimination of the terpene and sesquiterpene hydrocarbons,
which are valueless as regards flavouring capacity, has
assumed quite extensive proportions of late years. These
concentrated oils are particularly useful in the preparation
of soluble essences for the mineral water trade and for
purposes which require more soluble flavouring materials
than the ordinary essential oils. The manufacture of
concentrated oils is, however, a matter of considerable
difficulty, requiring much skill and experience; it fre-
quently occurs that the delicate aroma of an oil is spoiled
by careless concentration, and it is generally recognised
that it is not advisable to carry such concentration too
far, the oxygenated constituents which form the odorous
principles of the oils being particularly susceptible to
heat and to the general conditions involved in the
concentration process.
In the purchasing of concentrated oils it is advisable
that they should be stipulated " terpeneless " or " terpene-
less and sesquiterpeneless," as many oils sold under the
label "concentrated" are either ordinary essential oils
containing an admixture of additional odorous constituent
or purely mixtures compounded from synthetic odorous
bodies.
105
106 FLAVOURING MATERIALS
Most terpeneless and sesquiterpeneless oils are produced
by fractional distillation of the ordinary essential oils
under reduced pressure. The terpene constituents distil
over first, then the sesquiterpenes, and finally the odorous
constituents, or the latter may be steam distilled after
eliminating the sesquiterpenes. Another method of
obtaining oils free, to a great extent, from terpenes and
sesquiterpenes is to mix them first with weak alcohol and
then distil. The distillate separates into two layers, the
top being terpenes and the bottom an alcoholic solution
of the odorous constituents. The latter is returned to
the still and redistilled. At first the alcohol carries with
it a proportion of oxygenated odorous bodies, but as the
alcoholic strength of the solution in the still diminishes
the terpeneless oil separates out in an oily layer. This
second process is more troublesome than the ordinary
distillation under reduced pressure, but is said to yield
concentrated oils of greater delicacy.
The following gives some of the chief points of interest
with regard to the principal concentrated oils :
Terpeneless Oils. Angelica Oil has about twenty
times the concentration of the ordinary essential oil ; its
solubility is about 2'5 parts per 100 parts of 70 per
cent, alcohol and 85 parts per 100 parts of 80 per cent,
alcohol. It has a specific gravity of about 0*951 and a
rotation of about 3.
Aniseed Oil is 1/5 to 2 times as concentrated as the
natural oil, its solubility being 3 vols. per 100 vols. 70 per
cent, alcohol, and 9 vols. per 100 vols. 80 per cent, alcohol.
Bay Oil is 2 to 3 times as strong as the ordinary oil.
It has excellent solubility, 35 vols. being soluble in 100
vols. 60 per cent, alcohol and 90 vols. in 100 vols. 70 per
cent, alcohol. Its specific gravity is about 1*03 to 1'04.
TERPENELESS OILS 107
Bergamot Oil has 2*5 to 3 times the strength of the
natural oil, 9 vols. being soluble in 100 vols. of 60 per
cent, alcohol and 50 vols. in 100 vols. of 70 per cent,
alcohol. Characters : Specific gravity, 0*883 to 0'888 ;
optical rotation, 7 to 10.
Caraway Oil is about double the strength of the ordinary
essential oil. Its solubility is 25 vols. in 100 vols. 60 per
cent, alcohol and 60 vols. in 100 vols. 70 per cent, alcohol.
It has a specific gravity of about 0*963 to 0*965 and an
optical rotation of + 58.
Celery Oil has eight times the concentration of the
natural oil.
Cinnamon Oil is T5 to 2 times the strength of the
natural oil. It has a solubility of 60 vols. in 100 vols.
70 per cent, alcohol.
Citronella Oil is about twice the strength of the ordinary
oil. It has a solubility of 2 parts per 100 of 70 per cent,
alcohol and 150 parts per 100 of 80 per cent, alcohol. Its
specific gravity is about 0*91 to 0*92.
Clove Oil is 1*5 times the strength of the ordinary oil,
50 vols. being soluble in 100 vols. 60 per cent, alcohol
and 100 vols. in 100 vols. 70 per cent, alcohol. The
specific gravity is about 1*07, and the optical rotation nil.
Coriander Oil is about 1*5 to 2*5 times the strength
of the natural oil. It is soluble 25 vols. in 100 vols. 60
per cent, alcohol, and 60 vols. in 100 vols. 70 per cent,
alcohol.
Geranium Oil is 1*5 to 2 times the strength of the
ordinary oil, 60 vols. being soluble in 100 vols. 70 per
cent, alcohol. It has a specific gravity of 0'89 to 0*90,
and an optical rotation of 1 to 2.
Ginger Oil is 5 to 10 times the strength of the natural
oil. It has a specific gravity of about - 90 to 0*91.
io8 FLAVOURING MATERIALS
Hop Oil has 8 times the flavouring strength of the
natural oil.
Lavender Oil has about 1*75 to 2 times the strength of
the ordinary oil. Its solubility is about 15 parts per 100
parts of 60 per cent, alcohol, and 55 parts per 100 parts
of 70 per cent, alcohol. The chief constituents are linalol
and linalyl acetate. Characters: Specific gravity, 0*893
to 0*898; optical rotation, about 5.
Lemon Oil is the chief of these products and is about
20 times the strength of the ordinary oil. Its solubility
is 10 to 20 vols. in 100 vols. 70 per cent, alcohol, and in all
proportions of 90 per cent, alcohol. Characters : Specific
gravity, 0*896 to 0*900 ; optical rotation, usually to - 8 ;
hydrocarbon content, 20 to 25 per cent. Sachsse &
Co. give a process in the P. & E.O.R., 1914, 262, for the
estimation of the latter figure, as well as some useful data
regarding terpeneless and sesquiterpeneless lemon oils.
Much sophistication is practised in the adding of lemon
grass citral to the oils. Such oils usually have the
characteristic lemon-grass or verbena odour.
Lemon-grass Oil consists principally of citral and has a
strength of about 1*5 times that of the natural oil. Its
solubility is about 60 vols. in 100 vols. 70 per cent,
alcohol. It has a specific gravity of 0*896 to 0*897, and
an optical rotation of 1 to 1 40'.
Limes Oil (distilled) is about 12 to 16 times stronger
than the ordinary oil. It has a specific gravity of about
0*92 to 0*93, and an optical rotation of about 2.
Mandarin Oil has about 60 to 70 times the strength of
the natural oil, its solubility being about 1*5 to 3 vols.
per 100 vols. of 70 per cent, alcohol, and in about equal
proportions with 80 per cent, alcohol.
Orange Oil is 35 to 50 times stronger than the ordinary
SESQUITERPENELESS OILS 109
oil, its solubility being about 50 parts per 100 parts of
70 per cent, alcohol. The specific gravity is usually about
0'894, but the optical rotation varies between wide limits
according to the degree to which the terpenes have been
extracted.
Rosemary Oil has about 6 times the concentration of
the ordinary oil, its solubility being 20 vols. in 100 vols.
60 per cent, alcohol, and about 60 to 70 vols. in 100 vols.
70 per cent, alcohol. It has a specific gravity of 0'939
to 0-94.
Sassafras Oil is about 1*5 times the strength of the
natural oil. It is soluble 4 vols. in 100 vols. 70 per cent,
alcohol, and 15 vols. in 100 vols. 80 per cent, alcohol.
Characters: Specific gravity, about 1-088 to 1*09; optical
rotation, +1 to +2.
Sesquiterpeneless Oils. These are in most cases
slightly stronger than the terpeneless oils and have
increased solubilities, being mostly soluble in all propor-
tions of 60 per cent, alcohol. The following are the
characters of a typical Sesquiterpeneless lemon oil :
specific gravity, 0'9003 ; optical rotation, 3 35'; citral
(Burgess method), 61 perjcent.
SECTION III
FLORAL, FRUIT AND COMPOUNDED FLAVOURS
CHAPTEK VIII
THE PREPARATION OF FLOEAL PERFUMES
THE two chief methods of preparing floral perfumes are
by distillation and by extraction. The former of these
methods has been described under the Preparation of
Essential Oils, and consequently will not be dealt with
further in this section. Distillation is used in the pre-
paration of rose, lavender and orange flower perfumes.
For some of the more delicate products, however, this
process is too drastic, and extraction by means of volatile
solvents or by fixed oils is practised.
EXTRACTION BY VOLATILE SOLVENTS
The apparatus employed for the extraction of the
odorous constituents of flowers by means of volatile
solvents resembles a large-scale Soxhlet apparatus. The
flowers are placed in a suitable chamber and impreg-
nated with the volatile solvent, means being provided
for siphoning off the solvent when it reaches a certain
level in the extraction chamber. The solvent, containing
the odorous constituents of the flowers, together with
other bodies such as flower wax, is evaporated at a low
PREPARATION OF FLORAL PERFUMES in
temperature, the vapours being condensed and the
solvent again supplied to the extraction chamber. In
the hands of experts this method of extraction is
almost ideal.
The solvent used is frequently petroleum ether of low
boiling-point, this liquid fulfilling most of the desideratums
of a solvent for such a purpose. It is without chemical
action on the odorous material ; it has no residual odour
after evaporation ; it dissolves all the odorous constituents
of the flowers ; it boils at a very low temperature and is
comparatively cheap.
The residual floral perfumes which remain after evapo-
rating the solvent are termed "concretes." They are
usually semi-solid and contain, in addition to the odorous
bodies, the flower wax and natural colouring matter.
From these " concretes " natural flower oils or " absolutes,"
of great concentration and solubility, are obtained by
methods which entail the precipitation of the wax. This
wax is of no odour value but retains the perfume of the
flowers with very great tenacity, a fact which makes the
using of " concretes" a matter of some difficulty. The
flowers for which this process is well adapted are as
follows: Carnation, cassie, hyacinth, jasmine, jonquil,
mignonette, narcissus, orange, rose, tuberose and violet.
EXTRACTION BY NON- VOLATILE SOLVENTS
The solvents used in this case are either vegetable or
mineral oils or fats. Perfumed oils or pomades are pro-
duced by macerating successive lots of the flowers in
warm oils or fats until the latter are saturated with
perfume. The process is only suitable for flowers which
have a fairly stable perfume, such as cassie, orange, rose
and violet. The more delicate flowers are treated by a
ii2 FLAVOURING MATERIALS
process which is known as "cold enfleurage." This
process entails the use of sheets of glass, or other
material, in wooden frames, the whole being termed the
chassis. Both surfaces of the glass are covered with
perfectly odourless fat, and flowers are spread on the
upper surface. The chassis are then stacked, so that
each layer of flowers has fat above and below it, for a
sufficient time to permit the flowers to become exhausted
of perfume. The process is repeated exactly as before,
using fresh flowers, except that the chassis are reversed,
that is, the undersides are now turned uppermost and the
flowers strewn upon them; they are then left until the
flowers are exhausted, and so on until the fat is saturated
with perfume. Up to recent years the operations of the
cold enfleurage process were performed entirely by hand.
In 1918, however, Messrs. Lautier Fils patented a machine
for stripping the flowers from the chassis after exhaustion,
and saving thereby much of the perfumed fat (see P. &
KO.R, 1918, 326).
The fats, lards, pomades or perfumed oils are repeatedly
extracted with alcohol, which is then chilled to remove
the fat, and in this manner floral extracts are obtained
which serve as the basis for the preparation of ottos for
the flavouring of cachous, creams, etc.
PRINCIPAL FLOWERS AND THEIR ODOURS
Carnation. The carnation, ceillet, or Diantkus caryo-
phyllus, is indigenous to Northern Africa and Europe. It
is grown extensively in France for its perfume. More
than two thousand many-tinted varieties are in existence.
The carnation plant is propagated from seeds, layers and
suckers. The perfume of the carnation has a decidedly
clove-like odour ; most synthetic carnation ottos are in
PREPARATION OF FLORAL PERFUMES 113
fact built up on a basis of iso-eugenol together with
methyl iso-eugenol.
Cassie. Cassie perfumes are prepared from the flowers
of Acacia Farnesiana, which was indigenous to the West
Indies, but is now grown in many countries, for example,
America, Africa, India, the Philippines, the. Levant and
Southern France. The plants are propagated from seeds,
and the bushes at maturity reach a height of 15 to 16 feet.
The crop of blossoms is taken from October to February,
each tree yielding about 1J to 2 Ib. of flowers. Cassie
perfumes are produced by extracting the flowers with both
fixed and volatile solvents. The pomade is produced by
the warm maceration method, and perfumed oils are also
produced by extracting the flowers with almond or olive
oil. Concretes and absolutes of cassie, produced by ex-
traction with volatile solvents, are offered on the market,
and these form convenient articles, from a perfumery
standpoint, because of their concentration. Other species
of cassie flowers, such as those derived from A. cavenia and
A. dealbata (Wattle), are worked up for their odorous
constituents. The constituents which up to the present
have been found in cassie extracts are : geraniol, linalol,
farnesol, benzyl alcohol, anisic aldehyde, cuminic and
decylic aldehydes, methyl salicylate and a violet-like
ketone.
Heliotrope. Many species of heliotrope are in existence,
the plant which grows in this country being Heliotropium
peruvianum. The heliotrope flowers grown in Southern
France are macerated for twenty-four hours in melted fat
to which they yield their perfume. Heliotrope extract is
produced by shaking the pomade with alcohol.
Hyacinth. The principal country as regards hyacinth
culture at present is Holland. Although many hyacinth
ii4 FLAVOURING MATERIALS
perfumes and flavourings occur on the market, they are
chiefly of synthetic derivation. It has been found to be
exceedingly difficult to obtain satisfactory results from the
flower. Enfleurage cannot be practised on account of the
flowers being gathered damp. Extraction with volatile
solvents yields as good results as can be obtained with
this flower, and it has been demonstrated that the best
yields of concretes are obtained from light-coloured single
blooms.
Jasmine. The jasmine which is grown in Southern
France for its perfume is the Spanish variety Jasminium
grandiflorum. It is grafted upon cuttings of English
jasmine, or white jasmine (J. officinale). The flowers
are harvested from July to October, the midday from
11 a.m. to 3 p.m. being the most suitable time for
collection. The cold enfleurage process was until recently
mainly used for the extraction of the perfume. Much of
the crop is now treated with volatile solvents for the
production of concretes and absolutes. The following are
the constituents of natural jasmine perfume : benzyl
acetate, linalol, linalyl acetate, benzyl alcohol, jasmone,
indol and methyl anthranilate. In the Chem. Zeit., 1910,
34, 910, mention is made of the finding of geraniol,
cinnamyl acetate, paracresol and p-cresol methyl ether.
Jonquil. The jonquil (Narcissus jonquilla, N.O. Amary-
llidacese) is cultivated at Grasse in Southern France for
its perfume. The bulbs are planted in September and
they flower in March. The perfume is extracted by en-
fleurage and by maceration with oils.
Lily of the Valley. Most lily of the valley perfumes
of commerce are derived from synthetic sources. The
natural perfume is chiefly obtained from the Convallaria
majalis, although the flowers of other plants are some-
PREPARATION OF FLORAL PERFUMES 115
times used in the production of " Muguet." The perfume
is extracted by the enfleurage process, and on account of
the small quantity of odorous material contained in the
flowers such pomades are very expensive.
Rose. Otto of rose, produced by distillation, has been
described under Essential Oils. In recent years, however,
concretes and absolutes produced by extraction with
volatile solvents have been offered on the market.
Tuberose. The tuberose, Polyanthes tuberosa, was in-
digenous to Mexico, but is now largely grown in Southern
France for its perfume. The harvest is gathered from
July to October, and the perfume is extracted by both
volatile solvents and enfleurage. The perfume obtained
by enfleurage contains methyl anthranilate, methyl salicy-
late, methyl benzoate, benzyl benzoate and benzyl alcohol.
Violet. The violet, Viola odorata, is grown over a very
wide area. Its cultivation for perfumery purposes is,
however, chiefly carried on near Grasse in Southern
France. The crop is gathered in November and December,
the flowers being picked in the morning. The flowers are
extracted with volatile solvents and with hot oils and
fats. Violet leaves are also extracted with volatile
solvents to produce a semi-solid, green paste which has
the odour of the leaf and which is used in violet
perfumes.
CHAPTEK IX
NATUEAL FEUIT PKODUCTS
Fruit Juices and Syrups. Natural fruit juices, just as
pressed from the fruit, that is, in an unconcentrated
condition, but which have been specially treated to prevent
deterioration, have a widespread usage in many branches
of foodstuff manufacture. The preparation of the juices
is mainly as follows : The fruits are first crushed between
stone rollers and then pressed to separate the juice from
the pulp. The flavours of several fruit juices, such as
black currants, gooseberries, blackberries, pears, apples,
plums, apricots, etc., are developed by a fermentation
process previous to pressing ; others, such as strawberry,
pine-apple, etc., are spoiled by fermentation, and the
fruit must therefore be treated in a fresh condition.
When such a fermentation is to be permitted, about
3 per cent, of sugar is added to the crushed fruits and the
mass allowed to stand for a week at a temperature of
80 F. The development of alcohol in the mixture assists
the precipitation of the pectinous matters, so that when
the mass is pressed the resultant juice is clearer than
that prepared from fresh fruit. After pressing, the
residual pulp is washed with a small quantity of water
to remove the remaining juice. The juice is then sterilised
at a temperature of 180 F. and stored in hermetically
sealed containers or in sulphured casks. During storage
the final clarification of the juice occurs.
116
NATURAL FRUIT PRODUCTS 117
A recent method of preparing fruit juice is described
in Ceil. Citrog., 1920, 5, 264. In this method the juice is
heated to 85 C. in a special pasteuriser, and then allowed
to settle at 50 C. It is then mixed with kieselguhr and
filtered through a filter press, again sterilised and finally
run into a sterile receptacle. Bulletin No. 241 of the
United States Department of Agriculture, entitled
"Studies in Fruit Juices," gives the result of some
experiments in the preparation and storage of fruit juices.
Syrups are made by mixing 13 parts of sugar with
7 parts of fruit juice and heating to about 170 F. to co-
agulate the albumen, which is then filtered off. If instead
of heating in an open vessel the syrup is brought to the
boil in a vacuum still, the vapours which distil over can
be condensed, and the first runnings, which contain odorous
bodies from the fruit, added to the syrup.
Concentrated Fruit Juices. Concentrated fruit juices,
fruit extracts or "concretes" of fruits are prepared by
several methods, most of which involve the concentration
under reduced pressure of the juice at as low a temperature
as possible. The usual method of making concentrated
fruit juice is to distil the ordinary juice in a vacuum still
at a low temperature until the required concentration is
achieved, collecting the first 10 per cent, of the distillate,
which contains the volatile odorous principles of the
juice. This first 10 per cent, of the distillate is again
distilled under reduced pressure, and the first runnings
added to the concentrated fruit juice, which is the residue
in the first distillation.
If it is desired to obtain a concentrated juice free from
pectin, the ordinary juice is concentrated in vacuum to a
certain bulk, an equal volume of alcohol added to pre-
cipitate the pectin and the liquid is filtered. The alcohol
u8 FLAVOURING MATERIALS
is then distilled off, the first runnings being redistilled
and added to the concentrated juice.
Ger. Pat., 285, 304, 1914, describes the preparation of
concentrated fruit juice by first dialysing the ordinary
juice in a cold chamber, to reduce its acid content, and
then concentrating under reduced pressure.
Fruit Aromas. Natural fruit aromas or aroma oils
are obtained by first extracting the fruit several times
with alcohol, then shaking the alcoholic extract with
specially purified petroleum ether. The petroleum ether
extract is distilled at a low temperature, and there remains
as residue the odorous constituents of the fruit, together
with fruit wax. The wax is eliminated by dissolving the
mass in alcohol and chilling the solution, when the wax
separates out and may be filtered off.
CHAPTEK X
COMPOUNDED FLAVOURS
NUMEROUS books have been published during the last few
years giving hundreds of perfumery and flavouring essence
recipes of more or less value, and to these the reader must
refer if he is in search of such. In preference to following
this procedure it is proposed to indicate the more im-
portant types of flavours (the principal ingredients being
marked A), making especial note of the bodies (marked
B) which are used for varying these types to yield dis-
tinctive products. The figures quoted represent quantities
which are in all cases given merely to form a basis for the
evolutions of new flavours.
Bitters. These are prepared by macerating mixtures
of vegetable bodies with equal quantities of alcohol and
water. The following are types of the most important :
Angostura. (A) Angostura bark 20, bitter orange peel
5, cinnamon bark 5, cinchona bark 5, tonka beans 5,
galanga root 5, cardamoms 10, ginger 5, cloves 10 ;
(B) zedoary root, cassia buds, gentian root, carob, calisaya
bark, lemon peel, chamomile.
Hamburg. (A) Cinnamon bark 20, cassia buds 20,
ginger 10, gentian root 15, cardamoms 5, bitter orange
peel 2 ; (B) nutmeg, cloves, zedoary root, centaury, galanga
root, grains of Paradise, quassia, laurel berries, buckbean
leaves.
120 FLAVOURING MATERIALS
Hop. (A) Hops 20, centaury 2, wormwood 1, gentian 1 ;
(B) zedoary, galanga root.
Orange. (A) Bitter orange peel 20, gentian root 15,
citron peel 10, cascarilla bark 5 ; (B) ginger, cusparia,
chiretta.
Essences for bitters are also prepared by the addition
of essential oils to the extracts prepared as above from
vegetable bodies.
Bouquet Essences. Natural floral flavours are in
many cases strengthened and cheapened by judicious
additions of synthetic perfumes, the types of synthetic
perfumes mentioned later being suitable for this purpose.
Many floral and bouquet perfumes, which are used as
flavouring agents, are compounded from combinations of
essential oils, floral extracts, animal and balsam tinctures
and synthetic products, the following being types :
Ambre Bouquet. (A) Essence of musk 10, vanillin 1,
essence of ambergris 40, benzyl acetate 2, otto of rose 1,
tinct. of benzoin 2, tinct. of styrax 2 ; (B) patchouli oil,
geraniol.
Bouquet de Fleurs. (A) Lemon oil 2, orange oil 2,
bergamot oil 3, lavender oil 1, triple extract of rose 4,
triple extract of violets 4; (B) tinct. of musk, tinct. of
ambergris, vanilla.
Carnation Bouquet. (A) Triple extract of rose 20,
orange flowers 20, violet 10, cassie 10, vanillin 2, oil of
bitter almonds 1 ; (B) oil of ylang-ylang, tinct. of civet,
oil of cloves.
Honeysuckle. (A) Triple extract of rose 40, vanillin 1,
benzaldehyde 1, triple extract of jonquil 50, methyl
anthranilate 1, oil of orris 10 ; (B) tinct. of benzoin,
esters of geraniol and citronellol, pimento oil, cedrat
oil, origanum oil.
COMPOUNDED FLAVOURS 121
Jasmine. (A) Linaloe oil 1, neroli oil 1, triple extract
of jasmine 40, bergamot oil 2 ; (B) tinct. of ambergris,
methyl anthranilate.
Lilac. (A) Tinct. of civet 10, oil of bitter almonds 1,
neroli oil 2, triple extract of tuberose 30 ; (B) benzyl
acetate, ylang-ylang oil, terpineol.
Narcissus. (A) Triple extract of tuberose 20, otto of
rose 1, triple extract of jonquil 20, benzyl acetate 2 ;
(B) tincts. of styrax and tolu, vanillin, heliotropin,
neroli oil.
Opoponax. (A) Neroli oil 1, otto of rose 1, triple
extract of jasmine 10, tinct. of musk 5, vanillin 2, oil
of bergamot 3, oil of lemon 1 ; (B) patchouli oil, tinct.
of orris, ionone, tinct. of benzoin.
Stephanotis. (A) Tinct. of musk 20, tinct. of orris
40, oil of bergamot 2, otto of rose 2, neroli oil 2 ; (B)
triple extracts of tuberose, jasmine, linalyl acetate, ylang-
ylang oil.
Violet. (A) Ionone 100 per cent. 10, oil of orris
20, triple extract of violet 30, otto of rose 1, triple
extract of jasmine 5 ; (B) linalyl acetate, triple extracts
of cassie and jonquil, tinct. of musk, ylang-ylang oil,
vanillin.
Cake Flavours. These are usually mixtures of essential
oils and synthetic materials diluted with alcohol. The
following are types :
Suiter Ess. (A) Butyric acid 100 per cent. 20, sweet
orange oil 10, benzaldehyde 2; (B) lemon oil, vanillin,
coriander oil.
Fruits. (A) Lemon oil 20, orange oil 30, vanillin 2,
strawberry essence 10, neroli oil 1, benzaldehyde 10 ; (B)
coriander oil, cinnamon oil, cardamon oil, clove oil.
Spice. (A) Cinnamon bark oil 20, clove oil 30, bitter
122 FLAVOURING MATERIALS
almond oil or benzaldehyde 60, lemon oil 60, sweet orange
oil 60 ; (B) fennel oil, nutmeg oil.
Floral Flavours. Natural. These consist of the
pomades, flower oils, concretes, etc., extracted with or
dissolved in the requisite amount of specially purified,
odourless alcohol to yield perfumes of the strengths of
triple extracts, quadruple extracts, etc., small quantities
of benzoin, tolu balsam, Peru balsam, styrax, cinnamic
alcohol, benzyl benzoate, musk, vanillin, coumarin, etc.,
being added to act as fixatives. Essential oils which are
extracted from flowers, such as neroli, lavender and rose
oils, are in many cases used either alone or in admixtures
because of their great strengths.
Synthetic. Acacia. (A) Anisic aldehyde 9, benzyl
acetate 1, phenyl acetic aldehyde 1 ; (B) geraniol, citronellol,
nonylic aldehyde. Or (A) Yara-yara 10, citronellol 2,
nerolin 1, cinnamic alcohol 1 ; (B) geraniol, methyl an-
thranilate, cinnamic aldehyde, methyl acetophenone.
Cassie. (A) Cinnamic aldehyde 12, ionone 100 per
cent. 1, indol 1, tinct. of musk 8, tinct. of civet 1 ; (B)
benzyl acetate, methyl eugenol, methyl iso-eugenol.
Carnation. (A) Eugenol 6, terpineol 8, iso-eugenol 6,
tinct. of musk 1, tinct. of benzoin 1 ; (B) coumarin.
Clover. (A) Iso-butyl salicylate 20, coumarin 10, helio-
tropin 10, vanillin 10 ; (B) linalyl acetate. Or (A) Benz-
aldehyde 2, eugenol 2, terpineol 6, amyl salicylate 2 ; (B)
geraniol, nerolin, ionone, tincts. of orris, civet and storax.
Cyclamen. (A) Linalol 10, phenyl ethyl alcohol 2,
phenyl acetic aldehyde 1, ionone 2 ; (B) nonylic aldehyde,
decylic aldehyde.
Hawthorn. (A) Anisic aldehyde 20, vanillin 5, geraniol
6, benzyl acetate 5 ; (B) heliotropin, coumarin, benz-
aldehyde, nonylic alcohol.
COMPOUNDED FLAVOURS 123
Hyacinth. (A) Phenyl acetic aldehyde 10, terpineol 4,
cinnamic alcohol 1 ; (B) methyl acetophenone, benzylidene
acetone.
Jasmine. (A) Benzyl acetate 10, indol 1, linalol 1,
methyl anthranilate 1 ; (B) nerolin, ionone, linalyl acetate,
geraniol, citronellol.
Lilac. (A) Terpineol 2, linalol 6, phenyl ethyl alcohol
3, cinnamic alcohol 1 ; (B) benzylidene acetone, phenyl
acetic aldehyde, decylic aldehyde.
Lily of the Valley. (A) Linalol 5, benzyl acetate 1,
phenyl ethyl alcohol 2, terpineol 3; (B) duodecylic
aldehyde, vanillin. Or (A) Linalol 10, nerolin 3, ter-
pineol 10 ; (B) benzyl acetate, ionone.
Moss Eose. (A) Geraniol 10, citronellol 2, cinnamic
alcohol 1, geranyl valerianate 1, citronellyl valerianate 1 ;
(B) octylic aldehyde, santalol.
Parma Violet. (A) Ionone 40, vanillin 2, synthetic
jasmine 20 ; (B) violet leaf extract.
Rose d'Orient. (A) Geraniol 5, citronellol 3, benzyl
acetate 1, cinnamic alcohol 1 ; (B) esters of geraniol and
citronellol, phenyl ethyl alcohol.
Tuberose. (A) Linalol 10, benzyl acetate 8, methyl
anthranilate 1 ; (B) duodecylic aldehyde.
Violet. (A) Ionone 5, benzyl acetate 2, indol 1, tinct.
of musk 4 ; (B) synthetic cassie, santalol.
White Lilac. (A) Terpineol 40, phenyl acetic aldehyde
4, methyl anthranilate 6 ; (B) benzyl acetate, tinct. of
benzoin, acetophenone.
White Eose. (A) Citronellol 10, phenyl ethyl alcohol
10, synthetic rose d'orient 20 ; (B) nonylic alcohol.
Fruit Flavours. These may be divided into two main
groups: (a) for flavouring clear beverages (soluble
essences), (b) for flavouring confectionery.
124 FLAVOURING MATERIALS
Soluble essences are made up by dissolving terpeneless
or sesquiterpeneless essential oils in alcohol, by shaking
ordinary essential oils, such as citrus oils, with alcohol or
mixtures of alcohol and water and separating the alcoholic
layer from the terpene layer, by preparing natural fruit
extracts in such a manner that they give clear solutions
on dilution and by compounding such natural fruit extracts
with artificial fruit esters.
Confectionery essences may be derived from natural
fruit extracts, from natural fruit extracts with additions
of artificial fruit esters and from artificial fruit esters
alone. The majority consist of a basis of natural fruit
extract strengthened and supplemented by artificial fruit
esters,' essential oils and synthetic chemicals. Such
mixtures of esters, essential oils and synthetic bodies as
the following are used for this purpose :
Apricot. (A) Ethyl butyrate 10, butyl butyrate 10,
ethyl acetate 5. ethyl valerianate 5, amyl acetate 7, amyl
alcohol 1 ; (B) benzyl acetate, benzyl propionate, eugenol,
anethol, synthetic peach oil, petitgrain oil, vanillin.
Banana. (A) Benzyl acetate 10, benzyl propionate 10,
ethyl butyrate 5, amyl butyrate 10, amyl acetate 5, sweet
orange oil 3, lemon oil 4 ; (B) petitgrain oil, vanillin,
ethyl sebacate, cinnamon oil, clove oil.
Cherry. (A) Amyl formate 10, oenanthic ether 6, ethyl
acetate 15, ethyl pelargonate 2, benzaldehyde 1, amyl
alcohol 1 ; (B) clove oil, vanillin, neroli oil, cinnamon oil,
ethyl cinnamate, ethyl benzoate.
Peach. (A) Amyl acetate 10, ethyl acetate 5, synthetic
peach oil 5, ethyl butyrate 2, benzaldehyde 1 ; (B) amyl
butyrate, vanillin, lemon oil, orange oil, petitgrain oil,
cardamom oil.
Pear. (A) Amyl acetate 20, lemon oil 2, orange oil 5,
COMPOUNDED FLAVOURS 125
bergainot oil 5 ; (B) ethyl acetate, amyl butyrate, clove
oil, vanillin, petitgrain oil, geranyl butyrate, geranyl and
citronellyl formates.
Pine-apple. (A) Ethyl butyrate 20, amyl butyrate 40,
amyl acetate 5, ethyl acetate 10 ; (B) ethyl pelargonate,
orange oil, lemon oil, vanillin.
Raspberry. (A) Amyl acetate 20, amyl butyrate 20,
ethyl acetate 5, butyl acetate 30 ; (B) oil of orris, ionone,
petitgrain oil, vanillin, clove oil, orange oil, ethyl nitrite,
amyl valerianate, benzyl acetate, methyl salicylate,
cinnamon oil.
Strawberry. (A) Benzyl acetate 10, amyl acetate 20,
amyl butyrate 10, ethyl butyrate 20, ethyl acetate 5,
methyl salicylate 1, ethyl cinnamate 1 ; (B) ethyl benzoate,
nerolin, coumarin, cinnamon oil, vanillin.
Fruit essences are usually dissolved or reduced to a
standard strength in mixtures of alcohol and water or
alcohol, glycerine and water. The high duty on alcohol,
however, has during the past few years caused a great deal
of experimenting to be done with a view to providing
other vehicles. For example, fruit essences are now being
offered on the market suspended in mucilages or emulsions
of gum acacia, tragacanth, etc. For special flavouring
purposes, vegetable fat, of a perfectly odourless and taste-
less nature, has been strongly flavoured with various
flavouring bodies and offered to foodstuff manufacturers,
for use in such goods as contain fat.
Herbal Beverage Extracts. These are prepared by
infusing the vegetable matters with hot water and con-
centrating the extracts Bunder reduced pressure. The
following are several types of vegetable mixtures:
Dandelion. (A) Dandelion root 2,0, ginger 15, liquorice
extract 10 ;/(<B) gentian, quassia.
126 FLAVOURING MATERIALS
Hop Ale.-A^ Hops 10, ginger 10, quillaia bark 5,
liquorice extract 3 ; (B) wormwood.
Horehound. (A) Horehound herb 10, ginger 2, liquorice
extract 5 ; (B) lemon peel, chillies, balm herb, gentian,
coriander seeds.
Sarsaparilla. (A) Sarsaparilla root 20, sassafras bark
30, liquorice extract 10 ; (B) ginger.
Liqueur Essences. These are prepared by maceration
of vegetable bodies with alcohol and water, either with or
without the addition of essential oils. The following are
two examples of the former type :
Benedictine. (A) Angelica root 30, angelica seeds 20,
cloves 6, balm herb 30, cinnamon bark 5, mace 5, arnica
flowers 5 ; (B) thyme, calamus, vanilla beans, tonka beans.
With the addition of (A) oils of peppermint 1, lemon 2;
(B) cardamom, orange, coriander.
Chartreuse. (A) Bitter orange peel 20, ginger root 5,
cinnamon bark 3, zedoary root 15, calamus root 10, iva
herb 10 ; (B) balm herb, galanga root, angelica, calisaya
bark, anise. With the addition of (A) oils of coriander 1,
angelica 1, thyme 1 ; (B) lemon, orange, oenanthic and
acetic ethers.
In some cases also mixtures of essential oils are used,
without vegetable extracts, as liqueur flavours.
SECTION IV
ODOROUS CHEMICAL PRODUCTS
CHAPTEK XI
ALCOHOLS, PHENOLS AND ALDEHYDES
Alcohols and Phenols. Anethol is similar in odour
and flavour to aniseed oil, from which it is obtained by
chilling. It is used as a flavouring material in many
classes of foodstuffs and beverages. Its melting-point is
22-5 to 23; congealing-point, 21 to 22; specific
gravity, 0'985 at 25 ; boiling-point, 235 ; and solubility,
1 vol. in 2 to 3 vols. 90 per cent, alcohol. Anethol has
been prepared by several methods. For example, Wallach
synthesised it from anisic aldehyde in 1907, while
Klages in 1902 devised a synthesis starting from anisol.
Benzyl Alcohol has a faint odour resembling jasmine.
In fact, it occurs naturally in jasmine and several other
flower oils, and also in small quantities, accompanied by
benzyl esters, in Peru balsam. Its chief use is as a
solvent in the preparation of non-alcoholic perfumes ;
especially is it useful in dissolving artificial musks. It is
also used as a fixative in floral extracts. Several methods
may be employed in its preparation, one of the simplest
being the boiling of benzyl chloride with water and lead
hydroxide. It is also obtained by reducing benzalde-
127
128 FLAVOURING MATERIALS
hyde and by boiling Peru balsam with aqueous caustic
potash. The pure alcohol boils at about 206 and has a
specific gravity of 1/0507 at 15. It is slightly soluble in
water, soluble in alcohol and ether.
Cinnamic Alcohol (Styryl alcohol) has an odour re-
sembling hyacinths to some extent. It is used principally
as a fixative for other perfumes in place of storax, from
which it is obtained. Cinnamyl cinnamate (styracin)
yields cinnamic alcohol when distilled with aqueous
potash. Cinnamic alcohol has a melting-point of about
33 C. and a boiling-point of 254 to 255 C.
Citronellol is one of the most important odorous bodies,
being used extensively in rose perfumes. Together with
geraniol, it forms the product which is known as rhodinol.
Citronellol may be obtained synthetically from menthol
and also by reduction from citronellal. It is, however,
usually obtained from Bourbon geranium and Java
citronella oils. It can be separated from geraniol by
heating the oil with 95 per cent, formic acid, which de-
composes the geraniol and reacts with the citronellol to
give citronellyl formate. Other methods of separating
citronellol from oils in which it is contained, admixed
with geraniol, are by heating the oil to 250 in an auto-
clave along with water and by heating with phthalic
anhydride. In both cases the geraniol is decomposed.
The commercial preparation of citronellol from geranium
oil is a matter of difficulty. The oil is first saponified
with alcoholic potash, the geraniol being partly converted
into methyl heptanol. Eepeated distillation under
reduced pressure is necessary to separate the methyl
heptanol owing to the similarity in boiling-points. The
separation of the geraniol and citronellol is then accom-
plished by means of formic acid or, preferably, phthalic
ALCOHOLS, PHENOLS AND ALDEHYDES 129
anhydride, as indicated above. The citronellol is purified
by redistillation.
The characters of citronellol are as follows : Specific
gravity, 0-858 to 0-862 ; refractive index, 1456 to 1/460 ;
optical rotation, -2 to +4; boiling-point, 225 to 226.
Great variations occur in the odour values of commercial
citronellols owing to the difficulty of eliminating
impurities.
Decylic Alcohol (n-primary) or Alcohol C 10 has a fatty
odour and is used in small quantities for producing dis-
tinctive tones in floral extracts. It is formed by the re-
duction of capric aldehyde with zinc dust and acetic acid.
It melts at -10 to -8 arid boils at 110 at 13 mm.
Duodecylic Alcohol (n-primary) or Alcohol C 12 is similar
in properties to decylic alcohol, being used along with
Narcissus and Tuberose extracts and also with neroli
perfumes as a fixative. It is formed by the reduction of
lauric aldehyde with zinc dust and acetic acid. It melts
at 13 to 15 and boils at 142 at 13 mm.
Eugcnol is the principal odorous constituent of clove
oil. It is used as the starting-point in the preparation of
vanillin, and also finds employment in many essences and
extracts, e.g. carnation. Its extraction from oil of cloves
is accomplished by treating the oil with potash. The
potassium salt of eugenol separates out, is pressed free
from terpenes, washed with alcohol and decomposed, with
the formation of eugenol, by adding mineral acid. An
alternative method utilises the combination of eugenol
with sodium acetate to form a separable compound.
The pure product is a colourless liquid boiling at 248,
having a specific gravity of 1*072 and a refractive index
of T544. It reddens litmus and reduces ammoniacal
silver solutions on standing, but not Fehling's solution.
9
130 FLAVOURING MATERIALS
When tested with ferric chloride in alcoholic solution it
gives a blue colour. With sulphuric acid it gives at first
a brown colour, then purple and finally claret. The
Analyst, 1900, 25, 265, describes a reagent specially
devised for testing for eugenol. It is made up by dis-
solving 10 gms. of a mercuric salt in 25 per cent,
sulphuric acid and diluting to 100 c.c. When 2 c.c. of
eugenol are shaken with 5 c.c. of the reagent and allowed
to stand, a pale violet colour develops.
Iso-eugenol, which occurs in small quantities in nutmeg
and ylang-ylang oils, has a finer odour than eugenol. It
is used in compound floral perfumes of the wallflower and
carnation types. It is produced by an isomerisation
process from eugenol, potash and heat being applied and
amyl, methyl, ethyl or butyl alcohols being used as
solvent, although processes have been invented of accom-
plishing the isomerisation by using water alone or by
dry-heating out of contact with air. Iso-eugenol is a
colourless liquid of boiling-point 262 ; specific gravity,
1-090 ; refractive index, 1'5685 to 1-5720. Ferric chloride
in alcoholic solution gives with iso-eugenol an olive-green
colour and sulphuric acid a pink colour changing to
brown.
Methyl eugenol and methyl iso-eugenol are constituents
of cassie and ylang-ylang perfumes. They are used in
extracts and essences of the carnation type. Eugenol-
methyl ether is prepared from eugenol by the action of
methyl iodide and caustic potash. Iso-eugenol-methyl
ether is prepared from eugenol-methyl ether by warming
it with alcoholic potash, or from iso-eugenol by the action
of aqueous potash and dimethyl sulphate. The boiling-
points of these two compounds are 247 and 263 re-
spectively.
ALCOHOLS, PHENOLS AND ALDEHYDES 131
Geraniol is one of the most commonly used odorous
bodies ; it forms the basis, along with citronellol, of many
rose perfumes. It is obtained commercially from citron-
ella and palma-rosa oils. The fact that geraniol forms a
crystalline compound with calcium chloride, which is
insoluble in organic solvents but is decomposed by water
into geraniol and calcium chloride, is utilised in the pre-
paration of pure geraniol. The following are the characters
of geraniol : Specific gravity, 0'883 to 0'886 ; refractive
index, 1476 to 1'478; boiling-point, 229 to 231.
Iso-styrone is a body possessed of a distinct rosy odour.
It is used to some extent as a fixative and basis for
perfumes of a rose and jasmine description.
Linalol is the chief odoriferous principle of several
essential oils, e.g. linaloe and bois de rose femelle oils.
It also occurs in a vast range of natural perfumes, e.g.
orange flowers, bergamot, ylang-ylang, jasmine, etc. Its
odour is about midway between lemon and rose oils, and
it is used in a great variety of perfumes of the same
nature as those mentioned above. It blends very well
with synthetics of the nerolin type. The linalol of
commerce is usually obtained by the fractional distillation
of linaloe oil. It may also be obtained by acting upon
geraniol with hydrochloric acid and saponifying the
product. Its specific gravity is 0'870 to O874 ; optical
rotation, -20 to +20; refractive index, 1464 to 1467 ;
boiling-point, 198 to 199.
Menthol is a crystalline body obtained by chilling from
Japanese peppermint oil. It finds a varied application
in the flavouring of many foodstuffs, medicinal prepara-
tions and toilet requisites. It has a melting-point of 42,
a boiling-point of 212 and an optical rotation of 43
to -50.
132 FLAVOURING MATERIALS
Nerol occurs, chiefly in the form of esters, in neroli,
rose, petitgrain, etc., oils. It is a stereo-isomer of geraniol,
and is formed along with terpineol and geraniol when
linalol is treated with acetic anhydride. Unlike geraniol,
it does not form a crystalline product with calcium
chloride. It has a specific gravity of about 0'881, boils
at 226 to 227 and is optically inactive.
Nonylic Alcohol or Alcohol C 9 has a rose-like, fatty
odour, blending well with essence of sweet orange and
perfumes of a rose, jasmine and neroli type. It is also
used in the production of bouquet perfumes and essences
of the milleneurs, eau de Cologne, etc., description. Its
caprylic ester occurs in sweet orange oil. It has a specific
gravity of about O840, a boiling-point of 211 to 213 or
102 at 13 mm. and a melting-point of 11.
Odylic Alcohol or Alcohol C 8 has a fatty odour re-
sembling lemon to some extent. Several octylic esters
occur in essential oils, e.g. male fern. The alcohol is
used in perfumes of the eau de Cologne type. It is
obtained from its acetyl derivative. It has a specific
gravity of 0'828 to 0'830 and boils at 196 to 197 or
95 at 13 mm. On oxidation it yields caprylic acid, which
melts at 16-5.
Phenyl-Ethyl Alcohol has a honey-rose odour and occurs
in otto of rose. It is a constituent of Grasse rose essence
and, being very soluble, is particularly to be found in
rose waters. During the last few years it has come to be
very largely used in synthetic rose perfumes and also for
harmonising many floral extracts. The a alcohol is
obtained by reducing acetophenone with sodium amalgam.
It boils at 203. The /3-alcohol, boiling at 212, is formed
by reducing phenyl-acetic aldehyde with sodium amalgam.
The commercial alcohol has a specific gravity of 1'020 to
ALCOHOLS, PHENOLS AND ALDEHYDES 133
T025, a refractive index of T530 to T535, is optically
inactive and boils at about 220.
Phenyl-Propyl Alcohol is contained in storax, from
which it is obtained in the manufacture of cinnamic
alcohol. It is also prepared synthetically. Its hyacinth
odour is less pronounced than is the case with cinnamic
alcohol, resembling more nearly phenyl-ethyl alcohol. It
is used for similar purposes to phenyl-ethyl and cinnamic
alcohols and also in extracts of a reseda type. Its pre-
paration is accomplished by reducing cinnamyl alcohol
with sodium amalgam.
Safrol is contained in sassafras and camphor oils. It
is prepared from the latter by chilling out the camphor
and repeatedly fractionating the remaining oil. In the
pure condition it is a liquid with a congealing-point of
11, a specific gravity of T106, a refractive index of
1-5385 and a boiling-point of 233.
Iso-safrol is prepared from safrol by heating the latter
with sodium ethylate to 200. It has a specific gravity
of 1127, a refractive index of T580 and a boiling-point
of 253.
Santalol is obtained by the fractional distillation of
sandalwood oil. It is used in the production of essences
and in medicine. Commercial santalol is a mixture of
two santalols, a-santalol and j8-santalol. a-Santalol has
a specific gravity of 0'980 to 0'984, an optical rotation
of to -1, a refractive index of 1-505 to T509 and a
boiling-point of 300. The characters of j8-santalol are
as follows: Specific gravity, 0*985 to 0'986, optical
rotation, -51 to -56; refractive index, 1-505 to 1-509;
boiling-point, 309 to 310.
Terpineol is very largely used as the basis of cheap
lilac, lily of the valley and similar perfumes. It is
134 FLAVOURING MATERIALS
necessary that the terpineol should be of a high degree
of purity when used for perfumery purposes. Eose,
geranium and ylang-ylang oils blend well with terpineol,
as also do benzyl acetate, geraniol, citronellol, heliotropin,
etc. Terpineol is obtained by the action of alcoholic
sulphuric acid upon pinene, or by distilling terpin with
very dilute hydrochloric acid. The commercial article is
a thick liquid with a specific gravity of 0*940, a boiling-
point of 216 to 218 and a refractive index of about
1-480.
Thymol is extracted from thyme and ajowan oils. It
is a powerful antiseptic, is soluble in 1100 parts of cold
water, in 900 parts of boiling water and readily in alcohol,
ether, chloroform, acetic acid, etc. It melts at about 51
and boils at about 233.
Undecylic Alcohol or Alcohol C n has a powerful and
retentive, fatty odour. It is used as a tixative because of
its stable nature. It melts at 12 to 11 and has a
boiling-point of 128 at 13 mm.
Aldehydes and Ketones. Acetophenone is a white
crystalline body melting at 21 to 22. It has a powerful
odour and is sometimes used in perfumes of the lilac,
mimosa, syringa, new-mown hay, etc., types. It is, how-
ever, rather acrid and is frequently substituted by methyl-
acetophenone, which is of a much more pleasant nature.
It blends well with terpineol, benzyl acetate, etc.
Acetophenone may be obtained by distilling calcium
benzoate with calcium acetate. It is, however, usually
prepared by the interaction of benzene, acetyl chloride
and aluminium chloride.
Anisic Aldehyde or Aubepine occurs in small quantities
in fennel and aniseed oils. It has the odour of hawthorn
blossom, is soluble in all proportions of alcohol and fatty
ALCOHOLS, PHENOLS AND ALDEHYDES 135
oils and forms an excellent basis for perfumes of the
hawthorn and new-mown hay types, blending well with
orange, petitgrain, ylang-ylang and neroli oils and also
with heliotropin, coumarin, etc. When exposed to the
air it oxidises rapidly to anisic acid, which has no odour
value, also it is affected by light and heat and consequently
it is necessary to keep it in full, coloured bottles in a
cool place. It is prepared by the methylation of p-oxy-
benzaldehyde or by the oxidation of anethol. It boils at
about 246 and has a specific gravity of 1*125 to 1*126.
Benzaldehyde is the chief odorous constituent of essential
oils of bitter almonds, peach kernel and apricot kernel.
For flavouring purposes it is necessary that the product
should be free from chlorine, and, as most artificially pro-
duced benzaldehyde on the market contains traces of
chlorine, this impurity should be tested for very rigorously.
Benzaldehyde is used as a substitute for bitter almond
oil in maraschino and other flavours. It is a colourless
liquid which rapidly oxidises to benzoic acid on exposure
to the atmosphere. Its specific gravity is 1 - 051 to 1*055,
it is optically inactive, its refractive index is about 1*545
and its boiling-point, 177 to 179.
Benzaldehyde may be prepared by many methods.
The Lauth and Grimaux process is as follows : Benzyl
chloride is boiled with "nitrate of lead or copper under a
reflux condenser for eight hours. The product is sub-
sequently purified by combining it with bisulphite of
soda, decomposing with sodium carbonate and steam
distilling. Several syntheses commence with benzal
chloride, e.g. Hermann-Schmidt oxidises this compound
with manganese dioxide and water, Caro heats it with
milk of lime under pressure and Bigot employs lead
oxide and water. When either benzyl or benzal chloride
136 FLAVOURING MATERIALS
is used as raw material, the finished benzaldehyde contains
traces of chlorine which are difficult to remove. Such,
however, is not the case if the product is manufactured
by the direct oxidation of toluene according to the follow-
ing patents: G-er. Pat., 101221, 1897, using finely divided
manganese dioxide in presence of sulphuric acid, DM.P.,
127388, 1900, using nickel oxide at 100 and Ger. Pat.,
175295, 1903, using manganese sulphate. An interesting
process for the catalytic production of aldehydes is also
described in Berichte, 1918, 51, 585. In this process
palladinised barium sulphate, containing 5 per cent, of
metal, is used, and excellent results are said to be obtained.
Chlorine may be tested for in benzaldehyde by heating
the latter with sodium and testing for chlorine as in
ordinary organic analysis, or by heating the benzaldehyde
with chlorine-free slaked lime to redness. The mixture
is then cooled, a small quantity of water added and then
pure nitric acid used as solvent, the acid solution being
tested for chlorine with silver nitrate. For a comparison
of the various methods of estimating chlorine in benz-
aldehyde, see P. & E.O.R., 1917, 41.
Benzaldehyde is best assayed by means of saturated
sodium bisulphite solution. The U.S.P. method makes
use of the phenyl hydrazone, but both this and the neutral
sodium sulphite method give unsatisfactory end reactions.
Benzylidene-acetone (Cumaranol or Cinnamyl-ketone) has
a very powerful and retentive coumarin-like odour. It is
used in perfumes of the sweet-pea, new-mown hay,
lavender, syringa, etc., types. It is formed when benz-
aldehyde and acetone are condensed according to Claisen's
reaction, using caustic soda as catalyst. Benzylidene-
acetone is soluble in alcohol and ether and forms a
crystalline compound with bisulphite of soda. It gives
ALCOHOLS, PHENOLS AND ALDEHYDES 137
an orange- coloured solution with concentrated sulphuric
acid.
Oarvone is contained in caraway, dill and spearmint
oils, from which it is extracted. It has a usage in the
flavouring of certain liqueurs. Its characters are as
follows: Specific gravity, 0-964; optical rotation, 60 to
60; refractive index, 1498 to 1-500; boiling-point,
225 to 230.
Cinnamic Aldehyde, which occurs chiefly in cinnamon
and cassia oils, is made synthetically by what is termed
the croton condensation between benzaldehyde and acet-
aldehyde in the presence of caustic soda and other alkalies,
alcohol being occasionally added to the mixture to assist
the reaction. Cinnamic aldehyde is a colourless to light
yellow liquid, having a pure cinnamon odour and the
following characters : Specific gravity, 1'055 to 1'058 ;
refractive index, about 1-6195; boiling-point, 248 to 252
(with decomposition), or 129 to 130 at 20 mm. pressure.
Citral is the chief odorous principle in lemon and lemon-
grass oils. The product on the market is prepared from
both sources ; the quality of that prepared from lemon-
grass oil is very much inferior in delicacy of odour to that
prepared fro-m lemon oil, and the price is proportionately
less. Citral has a very large range of usage for all
manner of flavouring purposes where a suggestion of
lemon is required. It is especially used in the prepara-
tion of soluble essences for use in the mineral water
trade. So-called " synthetic lemon oils " are produced
using lemon terpenes and lemon-grass citral ; these, how-
ever, are deficient in delicacy of aroma and can usually be
detected by their odour. Citral is interesting in that it
is the starting-point for the synthesis of violet perfumes
of the ionone type. It has the following characters:
138 FLAVOURING MATERIALS
Specific gravity, O895 ; optically inactive ; refractive
index, about 1-488; boiling-point, 228 to 229. An
interesting series of optical determinations on citral and
ionones is detailed in J. pr. CJiem., 1921, ii. 102, 305-331.
Citronellal occurs in citronella oil. The pure product
has about three times the odour value of the latter oil.
It has an intense melissa odour and is used in lemon,
geranium, eau de Cologne, etc. essences. The following
are its characters : Specific gravity, about 0'855 ;
optically inactive; refractive index, 1444 to 1*448;
boiling-point, 207 to 208.
Hydroxy citronellal is a fresh-smelling product which is
specially suitable for use in perfumes, such as lilac, lily of
the valley, cyclamen, etc. To be of any value it should
be pure and free from terpenes. 5 c.c. of the compound
should be soluble when shaken with 100 c.c. of 40 per
cent, sodium bisulphite solution.
Decylic Aldehyde or Aldehyde C 10 occurs in exceedingly
small quantities in oils of sweet orange, orris, neroli,
lemon-grass, etc. It has a soft, fatty odour and a medium
volatility. Its boiling-point is 75 to 76 at 2 mm., and
in a pure state it is a crystalline body melting at 23. It
is prepared, as are most of the fatty aldehydes of this
series, by distilling under reduced pressure the calcium or
barium salt of the corresponding fatty acid with barium
formate.
Duodecylic Aldehyde or Aldehyde C 12 is a very in-
teresting aldehyde, having in a diluted state a very fresh
odour. It blends well with essence of orange and violet
perfumes. Its boiling-point is 101 to 102 at 2 mm.,
and its melting-point 24. It usually appears on the
market dissolved in a solvent, e.g. benzyl alcohol.
Heliotropin is a white crystalline body possessing a
ALCOHOLS, PHENOLS AND ALDEHYDES 139
pleasant heliotrope odour. It melts at about 36-5 and is
soluble in 5 parts 95 per cent, alcohol. It is manufactured
from safrol. This latter body is converted into iso-safrol
by treatment with caustic soda at 105, and the iso-safrol
is then oxidised with potassium dichromate and sulphuric
acid, heliotropin being formed.
Heptylic Aldehyde (GCnanthol) or Aldehyde C 7 is a
body possessing an intense, even offensive odour. It must
be used with great discretion and in small quantities. Its
chief property is that it gives a note of freshness to other
odours.
lonone, Methyl- lonone and Artificial Violet Perfumes
find a very extensive use in the preparation of floral ottos,
extracts, etc. These latter contain both ionone itself and
the derivatives of a-ionone and |3-ionone, which are
combined in ionone. The delicacy of the finished artificial
violet perfume depends to a large extent on the purity
and derivation of the raw materials. Citral, derived from
lemon-grass oil, is the chief of these, and is obtained
from the oil by careful fractionation. Pseud o-ionone, or
homologous bodies, is first prepared by shaking with
acetone, or homologues of acetone, in presence of baryta
or sodium ethylate for two or three days. After the
separation and purification of the pseudo-ionone, it is
converted into ionone by an isomerisation process, using
sulphuric acid, hydrochloric or phosphoric acid, accord-
ing to whether a- or 0-ionone is required in pre-
dominance. As regards odorous properties, |3 -ionone is
rather more acrid than a-ionone, approximating more
nearly to natural violet perfumes than the latter, which
has an orris odour.
Methyl Acetophenone is possessed of a finer odour than
acetophenone ; it resembles coumarin, but is much stronger.
140 FLAVOURING MATERIALS
Its odour blends well with hello tropin, terpiueol, geranium
oil, cassie extract, etc., and forms the basis of mimosa
perfumes.
Methyl- Nonyl Acet aldehyde or Aldehyde C 12 has an
odour of the lemon or mandarin type ; it is used in eau de
Cologne and other bouquet perfumes.
Nonylic Aldehyde or Aldehyde C 9 is a fine, fatty odorous
body which occurs in small quantities in oils of rose, orris,
mandarin, and probably in limes. It boils at 69 to 70
at 2 mm., and melts at 5 to 7.
Octylic Aldehyde or Aldehyde C 8 occurs in oils of lemon,
orange and jasmine. It should only be used in extracts
in very small quantities. Its boiling-point is 56 at
5 mm., and its melting-point 13 to 10.
Phenyl Acetaldehyde (toluylic aldehyde), or Jacinthea, is
a liquid possessing an intense odour resembling hyacinth.
Its chief drawback is that it has a tendency to polymerise
quickly, so that it is necessary to keep it in full bottles in
a cool, dark place, or to dilute the pure liquid with an
equal volume of alcohol. In any case it is advisable to
specify that any of the product supplied is freshly
manufactured. It may be produced by an isomerisation
process from acetophenone, or from phenyl acetic acid by
heating with calcium hydroxide. It is, however, produced
in bulk from cinnamic or lactic acid. Jehl has devised a
process for its preparation by treating methyl cinnamate
in methyl alcohol solution with bromine followed by
caustic soda. The mixture is subsequently neutralised
with sulphuric acid, sodium carbonate added and steam
distilled, the phenyl acetaldehyde in the distillate being
extracted with ether. It boils at 209 to 210.
Vanillin is probably the most important and widely
used of all the synthetic flavouring materials. It is
ALCOHOLS, PHENOLS AND ALDEHYDES 141
extensively used in place of vanilla beans. The chief
method of production is by the oxidation of iso-eugenol.
It is also formed, however, by the oxidation of coniferyl
alcohol or coniferin, and by heating guaiacol with chloro-
form and caustic soda solution. It is said that a 95 per
cent, yield and an exceedingly pure product is obtained
by oxidising eugenol, iso-eugenol, coniferin or coniferyl
alcohol with air and ultra violet rays simultaneously at
a temperature of 50 to 60 (Journ. Soc. Chem. Ind., 1910,
1036).
Vanillin occurs in white monoclinic needles. It has a
melting-point of 81 and a boiling-point of 170 at 15 mm.
In hydrochloric acid solution it gives well-marked colour
reactions with ketones, phenols and other substances
contained in essential oils ; such a solution is in fact used
in the identification of essential oils. Vanillin is soluble
in 100 parts of water at 14, and readily soluble in alcohol
and ether. With ferric chloride it gives a blue coloration.
The adulterants which have been found in vanillin
are acetanilide, coumarin, heliotropin, acetyl iso-eugenol,
acetyl-salicylic acid, phthalic acid, sugar, guaiacol carbon-
ate and benzoic acid. Acetanilide may be detected by
boiling with potash, aniline being formed if acetanilide is
present. Vanillin is estimated by conversion into its
bisulphite compound, decomposing the same with acid
and extracting the vanillin with ether. The Chem. Zeit. }
1914, 38, 402, describes in detail the detection of adulter-
ants in vanillin, and this description is abstracted in the
P. & E.O.R, 1914, 150.
CHAPTEK XII
ESTERS AND UNCLASSIFIED ODOROUS BODIES
Esters. Amyl Acetate has a powerful odour resembling
" pear " and is known as pear essence. Its preparation is
accomplished by the reaction of amyl alcohol and sodium
acetate in presence of sulphuric acid. A method for the
commercial preparation of amyl acetate from the mono-
chlor derivatives of saturated hydrocarbons (pentyl and
hexyl chlorides) is described in Journ. Am. Chem. Soc.,
1916, 38, 1368. Amyl acetate has a specific gravity of
0-860 to 0*863, a refractive index of about 1400 and a
boiling-point of 138 to 139.
Benzyl Acetate is an important constituent of oils of
jasmine, ylang-ylang, neroli and essence of cassie. The
acetate prepared from benzyl alcohol and acetic acid is
usually less acrid than that prepared from other sources.
The product is offered on the market free from chlorine.
Synthetic jasmine oils and essences are based on benzyl
acetate, which is one of the most widely used synthetic
perfumes. It has a specific gravity of T061 to T064, a
refractive index of 1*500 to 1/504 and a boiling-point of
205 to 206.
Bornyl Acetate is contained in pine-needle oils, of which
it has the characteristic odour. It is prepared by heating
together borneol and acetic acid in presence of sulphuric
acid. Its specific gravity is 0'990 to 0'993 ; optical rotation,
142
UNCLASSIFIED ODOROUS BODIES 143
-39 to -37; refractive index, 14655 to 1-4665 ; and
boiling-point, 98 at 10 mm. For recent .work on the
preparation of bornyl esters, see Journ. Chem. Soc., 1921,
i. 115.
Citronellyl Acetate has an odour of a fruity type
resembling lavender to some extent. It is used for
shading the perfumes of rose, lavender, bergamot and also
in some bouquet extracts. It boils at 119 to 120 at
15 mm. ; its specific gravity is 0*892 to 0*901 ; and its
refractive index, 14455 to 1^490.
Ethyl Acetate finds a widespread application in the
preparation of artificial fruit essences. It has a character-
istic, pleasant, ethereal odour. Its preparation is
accomplished by distilling alcohol and acetic acid in
presence of sulphuric acid, or by heating together fused
sodium acetate, alcohol and sulphuric acid. It boils at
77'5, has a specific gravity of 0'903 to 0'906 and a
refractive index of 1-370 to 1'375.
Ethyl-Phenyl Acetate is a body having a honey-like odour.
It is used in perfumes, such as honey, and in essences
requiring a suggestion of wax.
Geranyl Acetate has an odour of a rose-lavender type.
It is used in rose, geranium, lavender, ylang-ylang and
rosemary perfumes. Its specific gravity is 0*914 to 0'918 ;
refractive index, 1462 to 1464; and boiling-point, 242
to 244.
Linalyl Acetate is a very widely used odorous body. It
is contained in very large proportions in bergamot, linaloe,
bois-de-rose femelle, etc., oils. Its chief usage is in blended
perfumes of the lavender, bergamot, etc. types. Artificial
bergamot oil contains linalyl acetate together with lemon,
orange or bergamot ter penes, and sometimes terpinyl
acetate. Linalyl acetate is usually made from oils of
144 FLAVOURING MATERIALS
Mexican linaloe and bois-de-rose feinelle, the latter
yielding the finer product. It may be produced in a pure
state by first preparing linalol-sodium and acting upon
the same with acetic anhydride. Linalyl acetate boils at
105 to 106 at 11 mm. or at 220 with decomposition; it
has a specific gravity of 0*905 to 0'912 and a refractive
index of 1452 to 1'453.
Phenyl-Ethyl Acetate is a compound which has a marked
fruity odour resembling peach to some extent ; it is Used
in conjunction with phenyl-ethyl alcohol in floral perfumes.
It has a specific gravity of 1*038 and a boiling-point of
232 to 233.
Phenyl-Propyl Acetate is possessed of a flowery odour
resembling, to some extent, linalyl acetate.
Terpinyl Acetate is used for the same purposes as geranyl
acetate in perfume blending. It occurs in several essential
oils, such as bergamot and lavender, and is produced
commercially from both turpentine and terpineol, the
latter yielding the finer product. It is particularly used
in cheap eau de Cologne and bouquet perfumes," and also
in essences for the perfuming of tobacco. It may be
produced in a pure state by boiling terpineol with acetic
anhydride and sodium acetate under a reflux condenser.
Its specific gravity is 0*955 to 0*960 ; refractive index,
1*464 to 1*465 ; and boiling-point, about 220.
Methyl Anthranilate occurs in neroli, tuberose, ylang-
ylang, gardenia and jasmine perfumes. It is used chiefly
in the blending of perfumes ^ this type, its chief
disadvantage being that it colours the extracts in which it
is used. Methyl anthranilate may be obtained by fusing
indigo with caustic potash, the potassium salt of
anthranilic acid being formed. The anthranilic acid is
set free and esterified by passing dry hydrochloric acid
UNCLASSIFIED ODOROUS BODIES 145
gas through its solution in methyl alcohol. It may
also be obtained from ortho-nitro-toluene by oxidation to
o-nitrobenzoic acid, this being then reduced to anthranilic
acid. Methyl anthranilate has a specific gravity of 1*168
and a melting-point of 24.
Amyl Benzoate has an amber-like odour and is used as a
fixative in the blending of perfumes. It is prepared by
passing dry hydrochloric acid gas through a mixture of amyl
alcohol and benzoic acid. It has a specific gravity of
1-002 to 1-003 and a boiling-point of 258 to 260.
Benzyl Benzoate is a practically odourless body melting at
20 to 21. It occurs naturally in Peru balsam and is used
as a substitute for the same in the fixing of extracts. It
is a good solvent for artificial musk. Its specific gravity
is 1120 to 1123; refractive index, 1'570 ; and boiling-
point, 324*.
Ethyl Benzoate is similar in odour to methyl benzoate
(see later), being used in essences such as new-mown hay,
meadowsweet, etc. It is prepared by passing dry
hydrochloric acid gas through a solution of benzoic acid in
alcohol. Its characters are as follows : Specific gravity,
about T050; refractive index, T504 to 1-505; boiling-
point, 210 to 213.
Methyl Benzoate (Artificial Niobe Oil) is used in
essences such as new-mown hay and meadowsweet. It is
obtained by distilling methyl alcohol and benzoic acid in
presence of sulphuric acid. Its characters are as follows :
Specific gravity, 1'094; refractive index, 1-518; and
boiling-point, 200.
Amyl Butyrate has an ethereal odour resembling
pine-apple to some extent. It is used in fruit essences
of the pine-apple, apricot type. Its preparation is
accomplished in a similar manner to that of ethyl
10
146 FLAVOURING MATERIALS
butyrate (see later), using, however, in this instance fusel
oil in place of alcohol. It has a specific gravity of 0'866
to 0'867, a refractive index of 1/413 and a boiling-point
of 170 to 180.
Benzyl Butyrate has an odour resembling jasmine, like
other benzyl esters. It is occasionally used in fruit
essences, e.g. apricot, banana.
Ethyl Butyrate of commerce is a liquid possessing a
pungent odour resembling pine-apple. It is used largely
in the manufacture of fruit essences. Its preparation is
achieved by distilling butyric acid and alcohol in presence
of sulphuric acid. Its boiling-point is 110 to 121;
specific gravity, 0'883 to 0'884 ; and refractive index, 1'392.
Geranyl Butyrate has a fine, rosy odour. It is used in
giving distinctive tones to rose, geranium, etc., perfumes.
It boils at 142 at 13 mm.
Phenyl-Ethyl Butyrate has a distinctive odour resem-
bling tea-rose. It is used in the blending of floral extracts.
Phenyl-Propyl Butyrale resembles benzyl butyrate in
odour, but is not so powerful.
Benzyl Cinnamate is used for similar purposes to ethyl
cinnamate. It is a solid body with a characteristic odour
resembling Peru balsam. Its boiling-point is 337 to 340
and its melting-point 32.
Ethyl Cinnamate has a fine odour resembling apricot.
It is used in the preparation of perfumed waters and eau
Cologne, in the latter case acting as fixative. It has a
cific gravity of about T054, a refractive index of 1'557
and a boiling-point of 260 to 265.
Methyl Cinnamate is a body of balsamic odour which is
used for similar purposes to ethyl cinnamate. Its specific
gravity at 36 is 1*041, its melting-point is 36 and its
boiling-point, 263.
UNCLASSIFIED ODOROUS BODIES 147
Benzyl Formate is an aromatic liquid of a sweet, cinna-
mon-like odour. It is used in heliotrope, jasmine, etc.
perfumes and in certain fruit flavours.
Citronellyl Formate has a rose-bergamot odour, which
makes it invaluable in the shading of perfumes of the
lavender, rose, eau de Cologne types. It has a specific
gravity of 0'905 to 0'913, a refractive index of 1450 to
1-453 and a boiling-point of 98 to 100 at 10 mm.
Ethyl Formate is used in artificial rum essences. It .is
prepared by distilling a mixture of alcohol, glycerine and
oxalic acid. It is a very volatile liquid, boiling at about
54-5.
Geranyl Formate has an odour resembling wild-rose. It
is used along with other geranyl esters and geraniol in
producing distinctive types of rose perfumes. It has a
specific gravity of about 0'925, a refractive index of 1451
to 1460 and a boiling-point of 113 to 114 at 15 mm.
Phenyl-Ethyl Formate is possessed of a very sweet,
pungent odour of the chrysanthemum type.
Phenyl-Propyl Formate has a distinctive odour recalling
honey and cinnamic alcohol.
Amyl Heptylate is possessed of a strong, fruity odour
and is used in extremely small quantities to create per-
fumes of a distinctive type.
Benzyl Propionate has a fruity odour and is used to
some extent in fruit essences of the banana, apricot, etc.
types. It is also employed in jasmine perfumes to add a
distinctive tone to the benzyl acetate.
Citronellyl Propionate has a fresh rosy odour and is used
to some extent in rose perfumes.
G-eranyl Propionate has an odour resembling bergamot.
It is used in perfumes such as lavender, bergamot, rose,
etc.
148 FLAVOURING MATERIALS
Phenyl- Ethyl Propionate is possessed of a fruity odour
of a rose type and is used for giving distinction to floral
extracts.
Amyl Salicylate is a liquid with a distinct clover-like
odour. It is used extensively as the basis of perfumes,
such as Calif ornian poppy, clover, trelie, orchidee, etc.,
and blends well with musk ambrette. Its specific gravity
is T050 to 1*053; refractive index, 1*505 to 1-507; optical
rotation, about +1 30'; and its boiling-point, 270 to 277.
Ethyl Salicylate has an odour resembling methyl salicy-
iate, or oil of wintergreen (see later). It is, however,
more delicate, sweeter, and altogether finer. It has a
specific gravity of 1*135, a refractive index of 1*523 and a
boiling-point of about 230.
Methyl Salicylate (Artificial Oil of Wintergreen) is used
in meadowsweet and new-mown hay perfumes. It is the
chief constituent of oil of wintergreen. Its characters are
as follows : Specific gravity, 1*185 ; refractive index, 1*537 ;
and boiling-point, 224. The Journ. Am. Chem. Soc.,
1917, 39, 820, gives an optical method for detecting im-
purities in methyl salicylate, using the benzoyl derivatives
of the ester. See also P. & E.O.R., 1914, 60, for a colour
test to distinguish synthetic and natural oils of winter-
green.
Ethyl Sebacate is used fairly extensively in fruit essences.
It has a specific gravity of 0'962 to 0'963 and a refractive
index of about 1*437.
Ethyl Succinate has the following characters : Specific
gravity, about 1*050; refractive index, 1*42 to 1*43; boil-
ing-point, 210 to 215.
Amyl Valerianate is possessed of a pronounced apple-
like odour ; it is in fact known as apple oil and is used
in fruit essences of an apple type. It is produced by
UNCLASSIFIED ODOROUS BODIES 149
oxidising amyl alcohol, or by distilling sodium valerianate
with amyl alcohol in presence of' sulphuric acid. It has a
specific gravity of about 0'857 to 0*860, a refractive index
of 1410 to 1-417 and a boiling-point of about 188.
Benzyl Valerianate has a flowery odour somewhat re-
sembling phenyl-ethyl acetate.
Bornyl Iso- Valerianate is a colourless liquid possessing
a powerful, camphor-like odour. It is used to a small
extent in perfumery. Its preparation is achieved by
esterifying borneol with iso-valerianic acid. Its physical
properties are as follows : Specific gravity, 0'954 to 0*956 ;
refractive index, about 1462 ; optical rotation, about 35 ;
and boiling-point, 255 to 260.
Ethyl Valerianate has the characteristic odour of pine-
apple and is used in fruit essences of many types. It is
prepared by distilling sodium valerianate with alcohol in
presence of sulphuric acid. Its specific gravity is about
0-895 and its boiling-point 133 to 134.
G-eranyl Iso-Valerianate has an odour of a rose type
and is used for giving distinction to rose perfumes. It is
prepared by esterifying geraniol with iso-valerianic acid.
It boils at 135 to 138 at 13 mm.
Phenyl-Ethyl Valerianate is a liquid with a pronounced
rose-leaf odour.
Styrolyl Valerianate has a strong odour of jasmine, and
is used in very small quantities in jasmine and narcissus
perfumes.
Other Odorous Bodies. Coumarin is a white crystal-
line body with an odour resembling new-mown hay. It
is the chief odorous constituent of tonka beans and has an
extensive usage, both alone and in combination with other
odorous bodies, as a flavouring agent. The starting-point
in the preparation of coumarin is phenol, this being
150 FLAVOURING MATERIALS
condensed with chloroform by heating to a temperature
of 60 to 65 in the presence of caustic soda to form
salicylic aldehyde. This latter substance is purified
and heated with acetic anhydride and sodium acetate,
coumarin and aceto-coumaric acid being formed. The
mixture is heated with water and the aceto-coumaric
acid is decomposed, giving coumarin and acetic acid.
Coumarin is recovered from the reaction mixture by
steam distillation. Other methods of preparing cou-
marin are by heating phenol with malic acid and zinc
chloride or sulphuric acid and by treating o-oxy-phenyl
propionic anhydride with bromine at 170. Coumarin has
a melting-point of 67 and a boiling-point of 290. The
P. & E.O.R., 1918, 81, cites a case in which terpin hydrate
was discovered as an adulterant of coumarin to the extent
of 30 per cent.
Brom-styrol (Hyacinthine) is a body having an intense
hyacinth-like odour. It has the advantage of being more
stable than phenyl acetaldehyde. It blends very well
with, and has a distinct freshening effect upon, lilac, helio-
trope, new-mown hay and rose perfumes. Alpha-brom-
styrol is prepared by heating dibrom-hydrocinnarnic acid
with water. The auto-oxidation of brom-styrol to brom-
acetophenone is explained in Compt. Rend., 1921, 172,
162-165.
Diphenyl Ether is a crystalline body which has an odour
resembling geranium. It is formed by extracting a mole-
cule of water from two molecules of phenol. Sabatier and
Mailhe achieved this by dropping melted phenol into
thorium oxide at 400. This method, which was published
in 1913, is very interesting in that many similar compounds
having geranium odours can be produced in the same
manner, e.g. phenyl-cresyl ether, etc. (see also nerolin).
UNCLASSIFIED ODOROUS BODIES 151
Another method of producing diphenyl ether is to heat
sodium phenate with monobrom-benzene in presence of
powdered copper at a temperature of 200, the diphenyl
ether being recovered by distilling in steam. Diphenyl
ether melts at 28 and boils at 253.
Diphenyl Methane has an odour of green geranium
leaves. It is used in the production of cheap and lasting
geranium perfumes. It may be made by heating together
benzene and paraformaldehyde in presence of sulphuric
acid, or by the action of benzene on methylene chloride in
presence of anhydrous aluminium chloride. Its com-
mercial preparation is usually accomplished by the
ordinary Friedel Crafts reaction of benzene and benzyl
chloride in presence of anhydrous aluminium chloride.
Diphenyl methane melts at 26*5 and boils at 261.
Indol is contained to some extent in neroli, jasmine,
tuberose and other perfumes. It is very powerful in
odour and requires to be used with great care. It has
the drawback of colouring essences and extracts of which
it forms a component. The auto-oxidation of indol and
skatol has recently been the subject of a research, for
which see Jo urn. Chem. Soc., 1921, i. 127. It is synthe-
sised from anthranilic acid, also it is formed when o-nitro-
cinnamic acid is distilled with caustic potash and iron
filings, or when oxindol is distilled with zinc dust. The
usual method of preparation is by heating together aniline
and dichlorether. Indol is a colourless crystalline sub-
stance, melting at 52 and boiling at 253 with partial
decomposition. It is soluble in boiling water and distils
easily in steam.
Nerolin, Yara-yara and Bromelia. These bodies consist
of the ethyl and methyl ethers of naphthol. The com-
pounds, which are usually sold under the names nerolin
152 FLAVOURING MATERIALS
and bromelia, are the ethyl ether, and have an agreeable
odour somewhat resembling neroli. Yara-yara is the
methyl ether and has a powerful odour resembling acacia.
Nerolin and yara-yara are used in cheap eau de Cologne
perfumes and sachet powders. They can be produced by
several methods, e.g. |3-naphthol, hydrochloric acid and
ethyl or methyl alcohol are heated together in an autoclave
for eight hours, or the sodium salt of /3-naphthol is heated
on a water bath with ethyl or methyl bromide or iodide, in
ethyl or methyl-alcohol solution. A method devised by
Sabatier and Mailhe makes use of thorium oxide as a
catalytic agent. |3-naphthol in ethyl or methyl-alcohol
solution is passed over the thorium oxide at a temperature
of 240 to 260. Nerolin melts at a temperature of 37,
while yara-yara melts at 70 and boils at 294 to 295.
Par a-Cresol-Methyl- Ether is a constituent of natural
ylang-ylang and canaga oils. It has a powerful odour
and forms the basis of synthetic perfumes of this type.
It is produced by methylating the sodium salt of para-
cresol with dimethyl sulphate. Its specific gravity is
0-975 and its boiling-point 176'5.
Skatol is the |3-methyl derivative of indol. It is pre-
sent in narcissus perfumes and also in natural civet and
musk. Its odour is most repulsive in a pure state and,
like indol, it has to be used in very small quantities. It
occurs in the products of decomposition of substances
containing albumen or albuminous materials. It may be
prepared by fusing egg albumen with caustic potash or by
the natural decomposition of pancreas.
Synthetic Musks. Musk Xylol has a very extensive use
in perfumery and flavouring materials. Its chief draw-
back is its comparative insolubility in alcohol. It dissolves
in the proportion of 6 gms. per litre of 95 per cent, alcohol.
UNCLASSIFIED ODOROUS BODIES 153
Its solubility in benzyl benzoate is about 280 gms. per
kilo, and in ethyl phthalate about 135 gms. per kilo. A
frequently occurring impurity is trinitro-xylol, and this is
tested for by shaking, in a closed tube, equal weights of
the product and benzol. When trinitro-xylol is absent,
the product is totally soluble. Its melting-point is 112
to 113. Musk xylol is the original synthetic musk pre-
pared by Baur by condensing pure meta-xylene and
tertiary butyl chloride in the presence of aluminium
chloride, and nitrating the hydrocarbon produced, after
purification, with a mixture of fuming nitric and sul-
phuric acids.
Musk Ketone resembles natural musk in odour more
nearly than does musk xylol. It melts at 130, and is
prepared by condensing butyl toluene and acetyl chloride
in the presence of carbon disulphide and aluminium
chloride and nitrating the product.
Musk Ambrette melts at 85. It is much more power-
ful in odour than musk xylol and musk ketone, and has,
in addition, a pleasant suggestion of ambrette. It is pre-
pared by condensing meta-cresol with butyl chloride,
nitrating the product and converting it into its methyl
ether.
INDEX
Absinthe, 36, 54.
oil, 53.
Absolutes, 111.
Acacia, 122.
Acacia cavenia, 113.
dealbata, 113.
Farnesiana, 113.
Acetanilide, 51, 141.
Acetic acid, 82.
Acetone, 65.
Acetophenone, 123, 134.
Acetyl iso-eugenol, 141.
Acetylatioo, 62.
Acetyl-salicylic acid, 141.
Achillea millefolium, 54.
Acid value, 62.
Acorus calamus, 37, 75.
Adulterants of spices, 22 et seq.
Agaracin, 34.
Agaric, 34.
Ajowan oil, 101, 134.
Albright, 52.
Alcohols, 62, 127 et seq.
Aldehydes, 64, 134 et seq.
A Ilium cepa, 76.
sativum, 40, 76.
Allspice, 1.
Allyl-iso-thiocyanate, 14, 32, 82.
-propyl disulphide, 76.
Almond shells, ground, 22.
Aloe chinensis, 34.
Perryi, 34.
vera, 34.
Aloes, 34.
Aloin, 34, 35.
Aloysia citriodora, 104.
Alpinia galanga, 40, 77.
ojficinarum, 40, 77.
Ambergris, 56.
tincture, 120, 121.
Ambre bouquet, 120.
Ambreine, 56.
Ambrette oil, 92.
Amomum melegueta, 44, 77.
Amygdalin, 53, 96.
Amyl acetate, 124, 125, 142.
alcohol, 80, 94, 124.
benzoate, 145.
butyrate, 124, 125, 145.
eudesmate, 94.
formate, 124.
heptylate, 147.
salicylate, 122, 148.
valerianate, 125, 148.
Amylo-dextrine, 15.
Anacyclus pyrethrum, 45.
Analysis of spices, 28 et seq.
special methods, 30 et seq.
Analytical constants of spices, 3,
4, 6, 9, 10, 12, 13, 15-1 7,' 20.
Anethol, 92, 102, 103, 124, 127.
Angelic ester, 80.
Angelica, 35, 54, 126.
Angelica archangelica, 35, 101.
atropurpurea, 35.
Angelica oil, 101, 106, 126.
Angostura bark, 35, 119.
bitters, 119.
Animal products, 56 et seq.
Anise, 35, 54, 126.
Star, 35.
Aniseed oil, 60, 61, 101, 106, 134.
Anisette de Bordeaux, 36.
de Hollande, 36.
Anisic acid, 92.
aldehyde, 92, 113, 122, 127, 134.
Anonacese, 77.
Anthemis nobilis, 46, 80.
Anthemol, 80.
Apiol, 104.
Apium graveolens, 37, 102.
Apple oil, 148.
156
INDEX
Apricot, synthetic, 124, 145-147.
Apricot kernel oil, 96, 135.
Aretium lappa, 37.
AristolocMa serjientaria, 53.
Arnica, 36, 126.
oil, 80.
Arnica montana, 36, 80.
Aroideae, 75.
Aromadendral, 94.
Aromadendrene, 94.
Artemisia absinthium, 53, 81.
dracunulus, 81.
maritima, 81.
Asarone, 75.
Asparagin, 39, 43.
Asperula odorata, 53.
Aube"pine, 134.
Austerweil, xiii.
Azulene, 80.
Balm, 36, 126.
oil, 82.
Balsams, 54 et seq.
Banana, synthetic, 124, 146, 147.
Barclay, 31.
Barosma betulina, 98.
crenulata, 98.
serratifolia, 98.
Barrel, xiii.
Baudrexel, xiii.
Baur, 153.
Bay oil, 65, 93, 106.
Bayberry, 2.
Bean flour, 25.
Beers, 38, 41-43, 45, 46, 49.
Benedictine, 35, 42, 126.
Bennett, C. T., 64.
Benzaldehyde, 69, 85, 90, 93, 96,
97, 120, 122, 124, 135.
Benzoic acid, 51, 54, 56, 141.
Benzoin, 54, 122.
tincture, 120-122.
Benzyl acetate, 95, 114, 120-125,
134, 142.
alcohol, 95, 97, 113-115, 127,
138.
benzoate, 55, 84, 122, 145.
butyrate, 146.
cinnamate, 55, 146.
formate, 147.
propionate, 124, 147.
valerianatf, 149.
Benzylidene acetone, 123, 136.
Berberine, 38.
Bergamot oil, 59, 98, 107, 120,
121, 125, 143, 144.
Bergaptene, 98.
Berry, 52.
Betula lenta, 78.
Betulacese, 78.
Betulase, 78.
Bigot, 135.
Bisabol myrrh oil, 79.
Bisabolene, 79, 98, 99.
Bitter almond oil, 69, 96, ] 20, 121,
135.
apple, 38.
Bitters, 37, 38, 40, 44-46, 54, 119.
essences, 36, 39, 47, 48.
Bohrisch, 32.
Boiling-point, 61.
Bois de rose oil, 89, 131, 143, 144.
Borneol, 70, 73, 77, 81, 84, 85, 87-
89.
Bornyl acetate, 71, 87, 142.
iso-valerianate, 149.
Bouquet essence, 120.
de Fleurs, 120.
Brassica alba, 12.
nigra, 12.
Brazil nut shells, powdered, 22.
Bromelia, 151.
Brom-styrol, 150.
Buchu oil, 98.
Buckbean, 36, 119.
Buckthorn, 17.
Buckwheat hulls, ground, 23.
Burdock, 37.
Burgess method, 109.
Bur sera alcsxylon, 79.
delpechiana, 79.
Burseracese, 79.
Busse, 31.
Butter essence, 121.
Butyl acetate, 125.
butyrate, 124.
Butyric acid, 82, 121.
alcohol, 94.
Cadinene, 70, 71, 77, 78, 82, 85,
87, 89, 91, 96.
Caffeine, 43.
Cajuput oil. 67, 91, 93.
Cake flavours, 36, 121.
INDEX
157
Calamene, 75.
Calameon, 75.
Calamus, 37, 126.
oil, 75.
California!! poppy essence, 148.
Calisaya, 37, 119, 126.
Camphene, 71, 73, 77, 84, 87, 9<
96, 98-100.
Camphor, 81, 84, 85, 87, 89, 91.
oil, 87, 89, 133.
Gananga odorata, 77.
Cananga oil, 77, 152.
Canarium commune, 79.
Canella alba, 53.
Cannabinacese, 79.
Caproic alcohol, 94.
ester, 80.
Capsica, 18, 126.
Capsicum annuum, 19.
fastigiatum, 19.
minimum, 19.
tetragoiium, 19.
Caramel, 51.
Caraway, 3.
oil, 102, 107, 137.
Oarbenia benedicta, 42.
Cardamom oil, 76, 121, 124, 126.
Cardamoms, 4, 119.
Carmel Monks liqueur, 35, 42.
Carnation, 111, 112, 122, 129.
bouquet, 120.
Caro, 135.
Caroba, 37, 119.
Carthartic acid, 48.
Cartharto-mannite, 48.
Carum ajowan, 101.
carvi, 3, 102.
copticum, 101.
Carvacrol, 85, 88.
Carvone, 74, 88, 91, 103, 137.
Caryophyllene, 92, 94, 95.
Caryophyllus aromaticus, 8.
Cascarilla, 37, 120.
Cascarillin, 37.
Cassia, 5.
oil, 90.
lead in, 69.
Cassia acutifolia, 48.
angustifolia, 48
Cassie, 111, 113, 122, 130.
extract, 120, 140, 142.
Castor fiber, 56.
Castoreum, 56.
Castorin, 56.
Catalytic production of aldehydes,
136.
Cayenne pepper, 19, 32. ^
Cedar-leaf oil, 70. ^<C
Cedarwood oil, 66, 70, 75, 87.
Cedrat oil, 98, 120.
Cedrene, 70.
Cedrenol, 70.
Cedrol, 70.
Celery oil, 102, 107.
seeds, 37.
Centaury, 38, 119, 120.
Chamce cyparis sphmroidca, 70.
Chamomile oil, 80.
German, 80.
Chamomillol, 80.
Charlock, 13.
Chartreuse, 35, 42, 126.
Chavica Roxburghii, 17.
Chavicol, 93.
Checkerberry, 49
Chenopodium ambrosiodes, 81.
Chenopodium oil, 81.
Cherry laurel oil, 96.
synthetic, 124.
Ohevreau, 32.
Chiratin, 38.
Chiretta, 38, 120.
Chlorine in benzaldehyde, 136.
Chloroform, 65.
Chrysophauic acid, 48.
Cinchona, 119.
Cinchona calisaya, 37.
succirubra, 46.
Cinchonidine, 46.
Cinchonine, 46.
Cineol, 67, 76, 77, 81, 83, 84, 87-
89, 91-95.
Cinnamein, 54.
Cinnamic acid, 54, 55.
alcohol, 55, 122, 123, 128, 147.
aldehyde, 85, 90, 122, 137.
Cinnamomum camphor a, 89.
cassia, 6, 90.
zelanicum, 5, 90.
Cinnamon, 5, 119, 126.
leaf oil, 65, 90.
oil, 90, 107, 121, 124, 125.
Cinnamyl acetate, 114.
ketone, 136.
158
INDEX
Citral, 66, 67, 74, 77, 83, 93, 94,
98-100, 104, 108, 109, 137,
139.
Citraptene, 99, 100.
Citron oil, 98.
peel, 120.
Citronella oil, 68, 72, 83, 107, 128,
131, 138.
Citronellal, 63 68, 73, 74, 94, 128,
138.
Citronellol, 63, 74, 82, 83, 97, 122,
123, 128, 134.
Citronellyl acetate, 143.
formate, 125, 147.
propionate, 147.
valerianate, 123.
GitruUus colocynthix, 38.
Citrus aurantium, 100.
bergamia, 98.
bigaradia, 100.
limetta, 99.
limonum, 98.
madurensis, 100.
medica, 98.
var. acida, 99.
Civet, 56, 152.
tincture, 120-122.
Claisen's reaction, 136.
Clove oil, 65, 77, S>3, 107, 120, 121,
124, 125.
Clove stems, 8, 23.
Clover, 122, 148.
Cloves, 8, 30, 119, 126.
Coca, 38.
Cochin, xiii.
Cocking, 54, 63, 68.
Cocoa shell powder, 22.
Cocoanut shells, ground, 22.
Cola vera, 43.
Colocynth, 38.
Colocynthin, 38.
Columba, 38.
Columbic acid, 38.
Columbin, 38.
Commiphora abyssinica, 79.
kataf, 79.
myrrha, 79.
Composites, 80.
Concretes, 111.
Confectionery flavours, 50.
Congealing-point, 61.
Coniferse, 70 et seq.
Coniferin, 141.
Coniferyl alcohol. 141.
Conium, 35.
Convallaria majalis, 114.
Copaiba oil, 66, 87, 92.
Copaifera Langsdorffii, 92.
Cordials, 83.
Coriander, 10, 54, 126.
oil, 102, 107, 121, 126.
Coriandrum sativum, 10, 102.
Corin, xii.
Cornflour, 25.
Corrlgiola telephiifolia, 45.
Coumarin, 50, 51, 90, 122, 125, 135,
139, 141, 149.
Cresol, 78.
Cripps, 31
Croton elutaria, 37.
Cruciferse, 82.
Cubeb camphor, 96.
oil, 96.
Cubebic acid, 39.
Cubebin, 39.
Cubebs, 39.
Culinary flavours, 38, 40, 49.
Cumaranol, 136.
Cuminic aldehyde, 90, 103, 113.
Cummin cyminum, 103.
Cummin oil, 103.
Curcuma longa, 26, 76.
zedoria, 54, 77.
Curcumin, 26.
Cuscus oil, 75.
Cusparia bark, 35, 120.
Cuspariafebrifuga, 35.
Cusparidine, 35.
Cusparine, 35.
Cyclamen, 122, 138.
Cymbopogon cilratus, 74.
flexuosus, 74.
martini (Andropogon sclnxnan-
thus), 74.
var. sofia, 73.
nardus, 73.
Cymene, 85, 88-90, 94, 99, 101,
103.
Dainiana, 38.
Dandelion, 39, 125.
extract, 125.
Date stones, ground, 23.
Dean, 52.
INDEX
'59
Decylic alcohol, 129.
aldehyde, 99, 100, 113, 122, 123,
138.
Diallyl disulphide, 76.
Dianthus caryophyllus, 112.
Dicotyledons, 77 et seq.
Dihydrocuminol, 73, 98.
Dill oil, 103, 137.
Dimethyl sulphide, 87.
Diosphenol, 98.
Dipentene, 71-74, 79-81, 89, 91,
93, 96, 98-100, 103.
Diphenyl ether, 150.
methane, 151.
Dipt'ryx odorata, 49.
Duodecylic alcohol, 129.
aldehyde, 138.
Dupont, 68.
Duraiul, A., xi.
Dyer, 6, 30.
Eau de Cologne, 132, 138, 140, 144,
146, 147.
ficuelle process, 80.
Elder bark, 40.
flowers, 39.
Elecampane root, 40.
Elemi oil, 79.
Elcttana cardamom inn, 4, 76.
Emodin, 34.
Emulsin, 53, 96.
Enfleurage, 112.
Sponge process, 59.
Erythrcea centaurium, 38.
Essences, confectionery, 124.
soluble, 124.
Essential oils, 58 et seq.
analytical methods, 60 et seq.
distillation, 58.
expression, 59.
extraction, 59, 110.
sesquiterpeneless, 59, 109.
terpeneless, 59, 106.
Esters, 62, 142 et seq.
Estragon oil, 81.
Ethyl acetate, 124-126, 143.
benzoate, 124, 125, 145.
butyrate, 124, 125, 146.
cinnamate, 124, 125, 146.
citrate, 65, 82, 84.
formate, 147.
nitrite, 125.
Ethyl cenanthate, 124, 126.
olea'e, 82.
oxalate, 82.
pelargonate, 124, 125.
-phenyl acetate, 143.
phthalate, 65, 82, 84.
salicylate, 148.
sebacate, 124, 148.
succinate, 82, 148.
tartrate, 65, 82, 84.
valerianate, 124, 149.
Eucalyptus aggregata, 94.
amygdalina, 94.
Backhousia citriodora, 94.
dumosa, 94.
globulus, 94.
macarthuri, 94.
oleosa, 94.
polybractea, 94.
staigeriaiia, 94.
Eucalyptus oils, 67, 94.
Eudesmic esters, 94.
Eudesmol, 94.
Eugenia caryophyllata, 8, 94.
Eugenol, 75, 77, 89-91, 93-95, 122,
124, 129, 141.
Extraction of floral perfumes, 110.
Farnesol, 78, 97, 113.
Fatty oil, 66, 75.
Fellenberg, T. von, 52.
Fenchone, 103.
Fennel, 40.
oil, 61, 103, 122, 134.
Flavours, compounded, 119.
Floral extracts, 112.
flavours, 110 et seq, 122.
preparation of, 110.
synthetic, 122.
Foeniculum vlgare, 40, 103.
Foerster, Dr. R., xiii.
Formylatiou, 63.
Fraxinus ornus, 44.
rotundifolia, 44.
Friedel Crafts reaction, 151.
Froth heading, 44.
Fruit aromas, 118.
flavours, 123.
juices, 116 et seq.
concentrated, 117.
syrups, 116 et seq.
Furfuraldehyde, 80, 94.
i6o
INDEX
Galanga, 40, 119, 120, 126.
oil, 77.
Galipin, 35.
Galipoidine, 35.
Gallic acid, 34.
Gardenia perfume, 144.
Garlic, 40.
oil, 76.
Graultheria procumbens, 78.
Gaultherin, 78.
Gentian, 41, 119, 120, 125, 126.
Gentiana lutea, 41.
Gentianic acid, 41.
Gentianose, 41.
Gentio-picrin, 41.
Geraniacese, 82.
Geraniol, 73, 74, 77-79, 82-84, 89,
91, 95, 97, 99, 100, 104, 113,
114, 120, 122, 123, 131, 134,
147.
Geranium oil, terpeneless, 107.
Geranyl acetate, 62, 73, 74, 94, 143,
144.
butyrate, 125, 146.
caprylate, 74.
formate, 125, 147.
iso-valerianate, 149.
propionate, 147.
valerianate, 123.
Gilbard, 6, 30.
Gildermeister, 79.
Ginger, 10, 30, 119, 120, 125, 126.
exhausted, 12.
oil, 77, 107.
Ginger-grass oil, 73.
Gingerine, 11.
Ginseng, 41.
False, 41.
Gley, xii.
Glycerine, 51.
acetate, 65, 82, 84, 87.
Q-lycyrrhiza glabra, 43.
Glycyrrhizin, 43.
Grains of Paradise oil, 77.
Graminese, 72.
Griebel, 31.
Grimaux, 135.
Guaiac wood, 41.
Guaiacic acid, 41.
Guaiacinic acid, 41.
Guaiacol, 102, 141.
carbonate, 141.
Guaiaconic acid, 41.
Guaiacsaponic acid, 41.
Guaiac-saponin, 41.
Ouaiacum qfficinale, 41.
sanctum, 41.
Gurjun balsam, 66, 75, 87.
Hamburg bitters, 119.
Hanig, ix.
Hawthorn essence, 122, 134.
Hay era ft, xii, xiii.
Hefelmann, 31.
Helenin, 40.
Heliotrope, 113, 147, 150.
Heliotropin, 121, 122, 134, 135,
138, 140, 141.
Heliotropium peruvianum, 113.
Heptylic aldehyde, 139.
Herabolene, 79.
Herbal beverage extracts, 125 et
seq.
Herlitzka, xii.
Hermann- Schmidt, 135.
Hess, 51.
Hexyl alcohol, 80.
Hibiscus abelmosc/itis, 44, 92.
Hiltner method, 67.
Hober, xii.
Hoffmann, 79.
Holmes, E. M., 4, 5.
Holy thistle, 42.
Honey flavours, 143, 147.
Honeysuckle bouquet, 120.
Hop bitters, 120.
extract, 126.
oil, 79, 108.
Hops, 42, 120, 126.
Horehound, 42, 126.
extract, 126.
Humulene, 80.
Humulus Zupulus, 42, 80.
Hyacinth, 111, 113, 122, 128,
140.
Hyacinthine, 150.
Hydrocyanic acid, 53, 69, 96, 97.
Hydroxycitronellal, 138.
Hyssop, 42.
oil, 83.
Hyssopus qfficinalis, 42, 83.
Illicium religiosum, 36, 92.
verum, 36, 92.
INDEX
161
Indian geranium oil, 74.
verbena oil, 74.
Indol, 95, 99, 114, 122, 123, 151.
Inula Britannica, 36.
helenium, 40.
Inulin, 39, 40, 45.
lonone, 121-123, 125, 137, 138,
139.
Iridacese, 75.
Iris florentina, 44, 75.
germanica, 75.
pallida, 75.
Irone, 76.
Iso-butyl salicylate, 122.
-eugemol, 78, 93, 113, 122, 130,
141.
-myristicin, 93.
-pulegyl acetate, 63.
-safrol, 133, 139.
-styrone, 131.
-valeric ester, 82.
Iva herb, 126.
Jacaranda lancifoliata, 37.
Jacinthea, 140.
Jamaica pepper, 1.
Jasmine, 111, 114, 123, 131, 132,
149.
bouquet, 121, 144, 147.
extract, 121.
oil, 95, 127, 140, 142, 151.
Jasminium grandiftorum, 95, 114.
qfficwale, 114.
Jasmone, 95, 99, 114.
Jateorhiza columba, 38.
palmata, 38.
Jehl, 140.
Jonquil, 111, 141.
extract, 120, 121.
Jumeau, 32.
Juniper berries, 42.
berry oil, 70.
camphor, 71.
wood oil, 71.
Juniperus communis, 42, 70.
virginiana, 70.
Ketones, 64, 134 et seq.
Kettle, 54.
Kiesow, ix., x., xii.
Klages, 127.
Kola, 38, 43.
II
Kolanin, 43.
Kreis, 32.
Kuromoji oil, 91.
Labaune, 68.
Labiatse, 83.
Lauracese, 89.
Laurel, 43, 119.
oil, 91.
Laurus nobilis, 43, 91.
Lauth, 135.
Lautier Fils, 112.
Lavandula spica, 84.
vera, 43, 83.
Lavender flowers, 43.
oil, 83, 108, 120, 122, 144. .
Spike, 84.
Leguminosse, 92.
Lemon oil, 59, 83, 98, 108, 109,
120-12*2, 124-126, 137, 140.
peel, 119, 126.
Lemon-grass oil, 74, 104, 108,
137-139.
Lemon thyme oil, 89.
Levisticum officinale, 44.
Lignaloe oil, 79, 89, 121, 131, 143.
Lilac, 121, 123, 133, 134, 138,
150.
Liliacese, 76.
Lily of the valley, 114, 123, 133,
138.
Limene, 98, 99.
Limes oil, 99, 108, 140.
Limonene, 70, 73, 74, 76, 83, 87-
89, 91, 94, 98-100, 102, 104.
Linalol, 63, 73, 78-80, 82, 84, 85,
88, 91, 95, 98-100, 103, 108,
113, 114, 123, 131.
Linalyl acetate, 62, 84, 88, 95, 98,
99, 108, 114, 121-123, 143.
Lindera sericea, 91.
Linseed meal, pressed, 23.
Lippia citriodora, 104.
Liqueur essences, 126.
Liqueurs, 35, 36, 40, 42, 44, 48,
54, 96, 137.
Liquidambar orientalis, 55.
Liquorice, 43.
extract, 43, 125, 126.
Lovage, 44.
Loven, ix.
Lupulin, 42.
1 62
INDEX
Mace, 14, 31, 126.
Macassar, 31.
oil, 98.
Magnoliaceae, 92.
Mailhe, 150, 152.
Male fern oil, 132.
Malic acid, 43.
Malvaceae, 92.
Mandarin oil, 100, 108, 140.
Mandelic nitrile, 96.
Manna, 44.
Mannite, 39, 44.
Maraschino, 135.
Marchand, R., xiv.
Marjoram, 44.
oil, 85.
Marrubium vulgar e, 42.
Martelli, D., 32.
Malricaria chamomilla, 80.
Meadowsweet, 145, 148.
Melaleuca leucadendron, 93.
minor, 93.
Melissa, qfficinalis, 36.
Melissa oil, 83.
Melisse des Cannes, Eau de,
36.
Melting-point, 61.
Mentha arvensis, 86.
crispa, 88.
piperila, 45, 86.
viridis, 88.
Menthol, 45, 86, 87, 128, 131.
Menthone, 87, 98.
Menthyl esters, 45, 87.
Menyanthes trifoliata, 36.
Meta-cresol, 79.
Methyl acetophenone, 122, 123,
134, 139.
amyl-ketone, 90.
anthranilate, 95, 99, 100, 114,
115, 120-123, 144.
benzoate, 94, 115, 145.
chavicol, 81, 91-93, 102.
cinnamate, 146.
eugenol, 73, 93, 95, 122, 130.
heptenone, 73, 74, 79, 89.
ionone, 139.
iso-eugenol, 113, 122, 130.
nonyl acetaldehyde, 140.
salicylate, 78, 113, 115, 125,
148.
Mexican spice, 2.
Micrographs of spice adulterants,
24, 26.
of spices, 2, 7, 9, 11, 14, 18,
20.
Mignonette, 111.
Millefleurs essence, 132.
Mimosa, 134, 140.
Mineral oil, 65, 75.
Mitchell, L. C., 19.
Mitchella repens, 49.
Holler, 2.
Monocotyledons, 75 et seq.
Moschus moschiferus, 57.
Moss rose, 123.
Mountain damson, 48.
Muguet, 115.
Musk, 57, 122, 152.
ambrette, 148, 153.
essence, 120.
ketone, 153.
seeds, 44.
synthetic, 145, 152.
tincture, 121, 122.
xylol, 152.
Muskone, 57.
Mustard, 12, 31.
oil, 82.
iodine value of, 32.
Myrcene, 93.
Myristic acid, 76, 93.
Myristica fragrans, 14, 92, 93.
malabarica, 16.
Myristicacese, 92.
Myristicin, 93.
Myroxylon pereira, 54.
toluifera, 55.
Myrrh oil, 79.
Myrrholic acid, 79.
Myrtacese, 93 et seq.
Narcissus, 111, 152.
bouquet, 121, 149.
Narcissus jonquilla, 114.
Nerol, 78, 84, 89, 97, 99, 132.
Neroli oil, 99, 121, 122, 124, 132,
138, 142, 144, 151.
Nerolin, 122, 123, 125, 131, 151.
Neuss, 33.
New-mown hay, 134-136, 145,
148-150.
Niobe oil, artificial, 145.
Non-alcoholic essences, 125.
INDEX
63
Nonylic alcohol, 122, 123, 132.
aldehyde, 90, 99, 122, 140.
Nutmeg, 14, 119.
oil, 92, 122.
Oak wood dust, 24.
Ocotea caudata, 89.
Octylic aldehyde, 99, 123, 140.
Octylene, 98.
(Billet, 112.
(Enanthic ether, 124, 126.
(Enanthol, 139.
Oleaceae, 95.
Olfactory organs, xi.
Olive stones, ground, 23, 32, 33.
Onion oil, 76.
Opoponax bouquet, 121.
Optical rotation, 60.
Orange bitters, 120.
flowers, 111, 131.
extract of, 120.
oil, 59, 100, 108, 120-122, 124-
126, 132, 135, 138.
peel, 119, 120, 126.
Orchidee, 148.
Origanum dubium, 85.
hirtum, 85.
majorana, 44, 85.
majoranoides, 85.
onites, 85.
Smyrnceum, 85.
Origanum oil, 65, 85, 120.
Orris oil, 75, 120, 121, 125, 138,
140.
root, 44.
tincture, 121.
Otto of rose, 60, 97, 120-122, 131,
132, 134, 140.
stcaropteneless, 97.
Oxymyristinic acid, 101.
Oxy-penta-decylic acid, 101.
Palma-rosa oil, 74, 82, 131.
Palmitic acid, 92, 95, 102.
ester, 82.
Panax quinquifolium, 41.
Paprika, 19.
Para-cresol, 78, 95, 114.
methyl ether, 114, 152.
-cymene, 81, 92.
-methoxy - coumarinic aldehyde,
81.
Paradise grains, 44, 119.
Parma violet, 123.
Parry, E. J., xiii.
Parsley oil, 103.
Partridge vine, 49.
Passy, xiii.
Patchouli alcohol, 85.
oil, 85, 120, 121.
Pea flour, 25.
Peach, synthetic, 124, 144.
Peach-kernel oil, 96, 135.
Pear essence, 142.
synthetic, 124.
Pelargonium, capitum, 82.
odoratissimum, 82.
roseum, 82.
Pelletierine, 45.
Pellitory root, 45.
Pepper, 16, 32.
American or false, 17.
Cayenne, 19, 32.
Hungarian, 19.
long, 17, 33.
oil, 96.
red, 18.
Spanish, 19.
PeppermiLt, 45.
oil, 86, 126, 131.
Peru balsam, 54, 122, 127, 128,
145, 146.
Peruviol, 55.
Petitgrain oil, 100, 124, 125, 131,
135.
Petroselinum sativum, 103.
Peucedanum graveolens, 103.
Phellandrene, 68, 71, 77, 79, 81,
82, 87, 89, 90, 92-96, 99,
101, 103.
Phenols, 65, 127.
Phenyl acetic aldehyde, 122, 123,
140, 150.
ethyl acetate, 144, 149.
alcohol, 97, 122, 123, 132.
butyrate, 146.
formate, 147.
propionate, 148.
valerianate, 149.
propyl acetate, 90, 144.
alcoho', 133.
butyrate, 146.
cinnamate, 54.
formate, 147.
1 64
INDEX
Phlorone dimethyl ether, 80.
iso-butyric ether, 80.
Phthalic acid, 141.
Physeter macrocephalus, 56.
Phytosterolin, 47.
Picrcena excelsa, 45.
Pimenta acris, 2, 93.
di Tabasco, 2.
officinalis, 1, 95.
Pimento, 1.
oil, 65, 77, 95, 120.
Pimienta, 19.
Pimpinella anisum, 35, 102.
saxifrage, 48.
Pineapple, synthetic, 125, 145,
146, 149.
Pinene, 70-72, 75, 77, 78, 82-84,
87-94, 96, 98-103.
Pine-needle oils, 71, 142.
Pinocamphone, 83.
Pinus australis, 72.
canadensis, 72.
ledebourdii, 72.
pectinata, 72.
pinaster, 72.
pumilio, 71.
sibirica, 71.
sylvestris, 72.
tceda, 72.
Piper cubeba, 39, 96.
nigrum, 16, 96.
Piperacese, 96.
Piperin, 16, 39.
Piperitone, 94.
Pogostemon patchouli, 85.
Poivrette, 23, 32, 33.
Polyanthes tuberosa, 115.
Poly gala senega, 48.
Polygalic acid, 48.
Polypodium vulgare, 45.
Polypody, 45.
Polyporus officinalis, 34.
Pomegranate, 45.
Prickly ash berries and bark, 45.
Prins, Dr. H. J., xiv.
Protium altissimum, 89.
Prunus amygdalus amara, 96.
laurocerasus, 96.
serotina, 53.
virginiana, 98.
Prussia acid, 53, 69, 96, 97.
Pseudo-ionone, 139.
Punica granatum, 45.
Pyre thrum root, 45.
Quassia, 45, 119, 125.
Quassin, 46.
Quercitannic acid, 30.
Quillia bark, 126.
Quinidine, 46.
Quinine, 46.
Ranc, xiii.
Rape seeds, 13.
Raquet, D., 31.
Raspberry, synthetic, 125.
Red Peruvian bark, 46.
sanderswood dust, 25.
Refractive index, 60.
Resins, 54 et seq.
Rhamnus cartharticus, 17.
Rheum qfficinale, 46.
palmatum, 46.
Rhubarb, 46.
Rice flour, 25, 33.
Richet, xii.
Roman caraway oil, 103.
chamomile, 46.
Rosa damascena, 97.
Rosacese, 96 et seq.
Rose, 115, 128, 131, 143, 149.
Rose de Mai, 97.
d'Orient, 123.
extract, 120.
geranium oils, 82.
Paul Nabonand, 97.
Ulrich Brunner, 97.
Rosemary, 47.
oil, 87, 109.
Rosmarinus officinalis, 47, 87.
Rum essence, 147.
Rumex alpinus, 41 .
Rutaceee, 98.
Sabatier, 150, 152.
Sabinene, 76.
Sachsse & Co., 108.
Safrol, 89-93, 133, 139.
Sage, 47.
oils, 87.
Salicin, 56.
Salicylic aldehyde, 56, 90.
Salvia officinalis, 47, 87.
sclarea, 88.
triloba, 88.
INDEX
165
Sambucus nigra, 39.
Sandalwood oil. 100.
Santalaceae, 100.
Santalal, 101.
Santalene, 101.
Sautalol, 101, 123, 133.
Santalum album, 100.
Santene, 101.
Saponification value, 62.
Sarsaparilla, 47, 126.
extract, 126.
Sarsasaponin, 47.
Sassafras, 7, 126.
oil, 91, 109, 133.
Sassafras qfficinale, 47, 91.
variifolium, 47.
Saxifrage, 48.
Schimrael, 55, 70.
test, 73.
Schinus molle, 17.
Schneider, 31.
Schwalbe, ix.
Scorzetta process, 59.
Sedanolic acid, 102.
Sedanolid, 102.
Sedanonic anhydride, 102.
Selinene, 102.
Senega, 58.
Senegin, 48.
Senna, 48.
Sennacrol, 48.
Sennapicrin, 48.
Sense of smell, xi.
of taste, vii.
Serpentary rhizome, 53.
Sesquiterpeneless oils, 109.
Shiu oil, 91.
Sievers, E., 32.
Simaruba bark, 48.
Simaruba officinalis, 48.
Sinapis nigra, 82.
Skatol, 152.
Smilax ornata, 47.
Solstein, 31.
Southall Brothers, 31.
Spanish verbena oil, 104.
Spearmint oil, 88, 137.
Specific gravity, 60.
Sperm whale, 56.
Spices, 1 et seq.
analytical constants of, 3, 4, 6,
9, 10, 12, 13, 15-17, 20.
Spices, micrographs of, 2, 7, 9, 11,
14, 18, 20.
Spike lavender oil, 84.
Sponge process, 59.
Spruce wood dust, 25.
Spugna process, 59.
Squaw vine, 49.
Star anise oil, 92.
Stearoptene, 97-100, 104.
Stephanotis, 121.
Sternberg, xii.
Stock, 31.
Stokes, A. W., 33.
Strawberry essence, 121.
synthetic, 125.
Styrax, 55, 122, 133.
tincture, 120, 121.
Styrax benzoin, 54.
Styrol, 54.
Styrolyl valerianate, 1 49.
Sugar, 141.
Sweet birch oil, 78.
flag, 37, 75.
pea essence, 136.
Swertia chirata, 38.
Sylvestrene, 71, 72, 81.
Synthetic floral flavours, 122.
Syringa, 134, 136.
Tamarinds, 49.
Tamarindus indica, 49.
Tanacetum vulgare, 49, 80.
Tannin, 37, 45.
equivalent, 30.
Tansy, 49.
oil, 80.
Taraxacin, 39.
Taraxacum qfficinale, 39.
Tarragon oil, 81.
Taste, organs of, viii.
sense of, vii.
Terebene, 72.
Terpeneless oils, 105 et seq.
Terpenes, 66, 90.
Terpin hydrate, 85.
Terpinene, 7$, 81, 85, 101.
Terpineol, 63, 76, 79, 81, 85, 89,
91-93, 98-100, 121-123,
133, 134, 140.
Terpinyl acetate, 62, 65, 143, 144.
Tetrahydrocymene, 80.
Thorns, 55.
1 66
INDEX
Thuja oceidentalis, 70.
Thujone, 53, 81, 83, 88.
Thujyl alcohol, 81, 83.
Thyme, 49 126.
oils, 65, 88, 126, 134.
Thymo - hydroquinone dimethyl
ether, 80.
Thymol, 88, 101, 134.
Thymus hyemalis, 89.
mastichina, 89.
serpyllum, 89.
vulgaris, 49, 88.
Tiglic acid, 82.
isobutyl ester, 80.
Tobacco perfume, 144.
Tolman, L. M., 19.
Tolu balsam, 55, 122.
tincture, 121.
Tonka beans, 49, 119, 126, 149.
Toothache tree, 45.
Trefle, 148.
Tri-chamomillol, 80.
Troccoli, A., 17.
Tuberose, 115, 123, 144, 151.
extract, 121.
Turmeric, 25, 32.
oil, 76.
Turmerol, 76.
Turpentine, 65, 71, 72.
Umbelliferse, 101.
Umbelliferone methyl ether, 80.
Undecylic alcohol, 134.
Valerian, 51.
Valeriana qfficinalis, 50
wallichii, 50.
Valeric acid, 82, 101.
alcohol, 94.
aldehyde, 93.
Vanilla, 51, 126, 141.
Vanilla planifolia, 50.
pompona, 50.
Vanillic acid, 51.
Vanillin, 51, 54, 55, 120-125,
140.
Vegetable flavouring bodies, 34
et seq.
Verbena oil, 104.
Verbena qfficinalis, 104.
triphylla, 104.
Verbenaceae, 104.
Vermouth, 35, 40, 54.
Verona- Rinati, G., 17.
Velivera zizanoides, 75.
Veti-vert oil, 75. '
Violet, 115, 123.
bouquet, 121.
extract, 120.
leaf extract, 123.
perfumes, 76, 138, 139.
Virginian prune, 53,
red cedar, 70.
snake root, 53.
Viverra civetta, 56.
civettina, 56.
malaccmsis, 56.
megaspila, 56.
tMngalunga, 56.
zibetta, 56.
Wallach, 127.
Wallis, T. E., 18.
Walnut shells, ground, 23.
Wattle, 113.
Wheat flour, 25.
White cinnamon, 53.
lilac, 123.
rose, 123.
Wichmann, 52.
Wild cherry bark, 53.
oil, 97.
Wintergreen oil, 78, 148.
Winton, 52.
Wood marjoram oil, 89.
Woodruff, 53.
Wormseed oil, 81.
American, 81.
Wormwood, 53, 120, 126.
oil, 81.
Xanthoxylum americanum, 45.
Yara-yara, 122, 151.
Yarrow, 54.
Ylang-ylang oil, 78, 120, 121, 134,
135, 142, 144, 152.
Zedoary oil, 77.
root, 54, 119, 120, 126.
Zingiber ojficinale, 10, 77.
Zingiberacese, 76.
Zingiberine, 77.
Zwaardemaker, xiii.
NOTES
NOTES
5 5070
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