Spice Notes in Perfumery

By Felix Buccellato, Custom Essence Inc., Somerset, New Jersey

~1(1[ lI<i\o (,11 ICYVIstli(l tlI:lt v:wic, tyis tlIc, spice of Iiff,.
It [ :111dso lx, wid tlmt i]) tlw world <Apicc WC,IIJVC,
3 grml(l vwirt ),. D<.filli]]g the limits of spit<. call IN. a
Iryillg twk. Wc usc dl p:trts OF;Iwide vwicty ofplw]ts
i,)cludillg I}lc w(A or Imrk, Ietlv(,s. flowers, Iruits
A SW(IS.
It GUI he s:{id in N genera] sense that anything we
add for tl:ivor or fragr<mce va{ue could he construed
:LSu spice. This study examir]es many of the more
cornrrmu spices that one would find on a good super-
nmrkct spice rack as WCIIas some that :~re relatively
obscure.

Use of Spices in Frsgrsnces

While most people are aware of how and where
spices are used, little is known about where and how
they are used in perfumes or fragrances, There is
scarcely a fragrance on the market that dots uot com
taiu some sort of spice note. The most commonly
used spice in fragrance and Ravor is vanilla or its
chcmicd surrogate 4 hydroxy 3 tmt~thoxyl)(;llzalde-
hydc, commonly known as vmillin.
The importance and widespread use of vanilla
along with chemicals like wmillin, ethyl vmillin, cou -
marin, hcliotropiue and anisic aldehy de, (which arc
all components of vanilla), ciumot he overstated. It is
difficult to identify fragrances of’ any type that do not
emp]oy these rrmterials to some degree.
Fragrances like Shalimar, Emcraude. Obsession,
Osciw de la Rents, Gloria Vanderbilt, Passion, Bd a
Versailles, and Lou-Lou employ vanilla as part of
0272-26&Y93/0305~
101$04,COIO0-C1%70Allured
Pubk,hgCorp.
L Spice Note s in Perfumery

their main theme. Msny other fragrances are depen- The spicy odor of lilac is due to cinnamic ddehyde
dent on vanilla or a vanilla chemical as a part of a bal- and cinnamic slcohol. These notes, blended with
samic foundation. other floral constituents like phenyl ethyl alcohol,
Some are built on the foundation of spices like geraniol and citronellcd create a pleasant lilac florsl
clove and cinnamon. Examples of these would be composition where the spicy character is not per-
Y(mth Dew, Opium, Cinnabar, Canoe, Brut, Pierre ceived as cinnamon, hut as lilac.
Cardin and of course Old Spice. Less obvious exsm-
ples which employ spice notes are Lair du Temps, Characterization of Venous Spices
Norrel], L’Origan, Paco Rabanne, Halston and The variety of spice notes found throughout nature
Aramis. The list is endless, is enormous. We sre in a continuing process, trying
Almost all fragrances use some type of spice note to to categorize, memorize and understand these natu-
brighten up the composition. They are all used in the ral wonders we call spice. This is no small undertalc
same manner as they are used for cooking. They are ing and the following pages attempt to bring some
not usually the dominant character but blend with order amd understanding to our current knowledge of
the main theme of the preparation and add life to the spice oils and their character. I will begin by grcmp-
flavor, ing the spices that consist mainly of a single chsracter
Like an artist or musician who searches for just the donating component.
right color or sound, we examine all the spices so we Although the spices listed in Group I predominant-
are familiar with their character and store them in ly consist of a single component, they we, of course,
our memory for judicious use at tbe proper moment. not entirely responsible for the full rich chsracter of
Many florals whose odors are well known would the total essential oil. For example, while cinnamon
not have the same sparkle without chemicals which contains ahout 80% cinnamic aldehyde, the total oil
we normally regard as spicy. Carnation and lilac sre is quite different. This is due to tbe variety and chw-
two that are quite spicy, the responsible constituent acter of the other constituents, most of them only in
for the odor of carnation is eugenol. Eugenol, most
normally associated with clove, is found in many flo-
rals includhg jasmin, ylang, rose, tuberose, gardenia
and many others.

—
Group 1:Spices with Single Components.

Characterizing
Spice % Component Charactar

Allspice 80 Eugenol Spies

Almond 95 Senzaldehyde Nutty/Almond
Anise 90 Anethole AniaelLicorice
Armoise 50 Thujone isomers M@ WVoody
Badiane 80 Anethole Licorice
Balsamite 80 l-Cafvone Minty
Sasil 64 Methyl Chavicol Licorics/Medicinal
Caraway 50 d-Carvone Grassy/Caraway
Cinnamon ❑ark 71 Cinnamic Aldehyde Cinnamon/Spicy
Cinnamon Leaf SO E“genol Clove/Spice
Clove SO Eugencd Clove/Spice
Estragon SO Methyl Chavicol Licorice/Medicinal
‘Leek — Oipropyl Disulfide Onion/Garlic
— — Allyl Methyl,
+ Methyl
. Propyl Sulfidesl
Mustard 80 Allyl Isothiccyanate Mustard/Pungent
Peppermint 50 Menthol + Mint
Menthone 20%
Perilla 50 Perilla Aldehyde Nutty
Spearmint 60 l-Carvone Mint
Wlntergreen 95 Methyl Salicylate Mint
Vanilla — Vanillin Vanilla/Powder

‘While leek may have many components, the most important

odor components are me sulfides, Other terpenes and classes
of chemicals play only a very minor role in the aroma profile.l

Vol. 15, Ssp*r/Octcbe.r 1993

 Spice Notes in Perfumery

trace quantities, that make a significant contribution examine the composition of coriander oil in detail.
to the overall odor and performance. Coriander oil consists primarily of 80% linalool.
Characterization of any complex (or simple) com- For those who appreciate the subtleties and intrica-
position is a difficult task. It is amdgous to a piece of cies of this complicated spice, it is not necessaty to in-
music. All the parts can be heard simultaneously, but dicate that Iinalool is not the characterizing agent of
no one part is obscured hy any of the other parts. It is this essential oil.
aquestionofbakmce and blend, rdldone very taste- Table I examines the composition of this interest-
fully, R is an analytical task to dissect the composition ing spice by separating the characteristic elements
and understand how it was composed originally. and grouping them by chemical class. z
In order to determine how the effect is achieved, Theodor characters of Coriander oil me: Citrus,
we begin by examining the individual component (lemon-like), Floral, Fruity, Spicy, Minty, Woody
parts until we find a component that is individually and Waxy.
responsible for the character of the whole. For ex- It is the combination of these characters and their
~ple, eugenol is quite characteristic of clove, Unfor- specificity to coriander that we keep in mind as we
tunately, this is not always the case. Even after we match their components to the coriander character.
discover several components, it is not always clear Table II illustrates the components, and their partic-
how they contribute to the overall composition. It ular contribution to the character of coriander.
often becomes necessary to reconstruct the composi- It is often the case that a chemical may contribute
tion, component by component, to determine how more than a single character. This is the case with
they interact. citronellol. It contributes both to the floral and to the
We have seen analysts focus on threshold to em- waxy character.
phasize theimportance oftrace ingredients, While Next, we will examine the oils that exhibit a slightly
threshold values are important forcomparisonpur- more complex character. The spices that have at least
poses, thesame values maynotbe vdidmd hence, two or more ingredients that chwacterize the flavor
not as useful in a composition. We can be certain that and aroma are listed in Group 11.
the physical properties or evaporation rate of one As in the previous group, the components in Group
component affects the properties of another. It u only give the shell of the character of the whole oil.
would be more accurate to assume that factors of po- In fact when we blend two or three of the constitu-
larity, volubility, and evaporation rate all play a role ents the difference is enormous. However, in almost
in an aroma profile. With these things in mind we will all cases, when we look at the blends of components

Tabla 1.Constituanta of coriandar oil groupad by chemical Claaa

19 Hydrocarbon 3 Thiazoles 9 Bases

a-Plnane Thiazole, 2,4,5-trimethyl Pyrazine, 2,3,5 trimethyl
Camphane Thiazole, 2-isopropyl, 4-methyl Pyrazlne, 2-mathyl &athyl 7 Aldehydes
@-Pinene Thiazole, Z-isobutyl, 4,5-dimethyl Pyrazine, 2-ethyl 5.methyl (E)2-Decenal
SabinenO Fyrazine, 2,3,5,6-tetramethyl Undacanal
Myrcene Pyrazine, 2-athyl 3,&dimathyl Dodecanal
2 (Ep) Oxidas
3-Carene Pyrazine, 2-ethyl 3,5-dimethyl (E)2-Dodecenal
&Caryophyllene epoxlde
a-Thujene Pyridlne, 2-butyl 2-Tridecenal
IJnalool oxide
a-Phellandrene Pyridine, 2-pentyl Geranial
Limonene Pyridine, 2-acetyl DeCanal
10 Alcohols
a-Terpinena
DodecanOl 1 Ketone
&Phellandrena 10 Furans
Citronellol Camphor
y-Terpinene Furan, 2-p+mtyl
Geraniol Furan, 2-haxyl
pCymene 2 Acids
Nerol
Heptadecane Furan, 2-octyl Acetic
Linalool
Octadecane Furan, 2-hexyl 5-melhyl Decanoic
a-Terpineol Furan, 3-(3-panteny l-4-methyl)
Ocimene
Oacanol Furan, tetrahydm 2-methyl- 4 Estam
Terpinolene
Terplnene-01-4
4-isopropany l-l -methylbenzene 2-vinyl-54 sopr0panyl Geranyl acetate
Elemol
p.-Caryophyllene Furan, tetrahydro 2-methyl- Linalyl acetate
Borneol 2-vinyl-5-isopropanol (Lilal alcohol) Isoamyl 3-methyl
3 Phanol!4 Furan, tetrahydro 2-methyl- Butanoate
2-isopropyl-5-mathyl phenol (Thymol) 2-vinyl-5-lsopropanoic acid (Davana acid)
1-Methoxy-4-propanyl bsnzene (Anethole) Furan-2-one, 5-methyl 5-vinyl (Lavander Iactone)
1-Allyl-5-methoxy-3,4-methylenadloxy banzena (Myristicin) Furan-2-ol, 5-methyl 5-vinyl

4/Pdumer & Flovorisl W, 15, S.pembsr/Octier 1993

 Spice Notes in Perfumery

in Table II, the basic character of tbe spice is recog- ponents that have been identified. In every case in
nizable. Group III the most important components have not
In the next section we will look at those spices yet been discovered.
which have a very complex character. It is often the Each spice has a distinct and unique character that
case that even after all the constituents have been re- stems from more than just tbe combination of the
combined the character is only approximate. In some identified components. As indicated above, the most
cases the final composition is not even recognizable. important components have not yet been identified
All of the components in the next group (Group III) for all of these. What might these components be? I
play an important role in the character of their re- feel they are trace ingredients with enormous im-
spective oils. After each oil I have indicated the com- pact. Compounds like pyrazines, thiazoles, sulfur and
nitrogen containing molecules along with unsatu-
rated aldehydes and ketones that exhibit very spe-
cific characters.
Group Ik Spices with two or more component. The fourth section of this examination of spices
might be viewed as the most difficult, There is a com-
Characterizing
mon denominator in that they all have a characteris-
Spice % Component Character
tic aroma of Black Pepper. While there are differ-
Bay 40 Eugenol Medicinal/Spit%
ences in constituents, they have a great deal in
10 Chavicol Medicinal/Splca
Cassia 70 Cinnamic Aldehyde CinnamonlSplc@ common. It is most interesting to note that the chw-
10 wMethoxy Cinnamon/Spice acter contributing component or components have so
Cinnamic Aldehyde far remained elusive to many scientists. We will ex-
Cumin 50 Cuminic Aldehyde Nutty/Fatty amine these in Group IV.
10 Oihydm Cuminic Nutty/Fatty
There are over 120 components identified in Black
Aldehyde
Oillseed 40 d-Carvone Grassy/Dill Pepper. They are composed of the following classes
30 a Phellandreno Woody/Citrus of chemicals. Forty-six hydrocarbons, 31 alcohols, 16
Dillweed 40 d-Carvone Grassy/Dll carbonyls, 1 acid, 10 esters, 11 bases, 2 ethers, 1 ni -
30 a Phellandrene Woodylatrus trile, 8 phenols, and 3 oxides.
Fennel SO Anethole Licorics
None of these chemicals is responsible for the ex-
10 Fenchone MlntyiWwdy
3 Methyl Chavicol Herb/Medicinal tremely powerful and characteristic aroma of black
Marjoram 40 Eucalyptol Medicinal/Minty pepper. It is possible to see the character contribu-
(Spanish) 15 Unalool Gtrus/Floral tion of Pam cymene and gamma terpinene as well as
Oregano (Greek) 65 Carvacrol Oregano/fvle5idnal other unsaturated hydrocarbons to the aroma of
7 Thymol Spicy/Medicinal
black pepper. However, it is not possible to achieve
6 Para Cymene Fresh/Spicy
Sage Spanish 15 Eucalyptol Medicinal the characteristic aroma of black pepper by mixing
(Lavandulifolia) 30 Camphor MinfylMedicind all of the above ingredients. This is a clear indication
Sage Oalmation 40 Thujone isomers Mint/Herbaceous that we have not identified the characterizing com-
(Officinalis) 20 Camphor Minty/Medcinal ponent(s) of black pepper.
Thyme 45 Thymol Spicy/Medicinal
It can further be seen that there are a great many
18 Para Cymene Spicy~erpene
2 Carvacrol Medicinal/Spice terpenes and sesquiterpenes in all three of these oils.
It has been my experience that many commercial ses-

Table Il. An illuetretion of the components reeponeible for the cherecter of corfender.’

Citrus character” Sabinene, myreene, a-phellandrene, hmonene, a-terpinene, p-phellandrene, ?-terpinene, rxymene,
ocimene, terpinolene, a-thujene. All 7 aldehydes with particular emphasis on (E) 2-decenal and geranial,
acetic acid and Iinalyl acetate.
Floral character Linalool, nerol, geraniol, citronellol and most of the 10 furans bsted in Table 1.
Fruity character Geranyl acetate, bnalyl acetate and isoamyl 3 methyl butanoate enhance the citrus character by
introducing tha sweat fruity f18vor.
Spicy character 2-isopropyl-5-methyl phenol and 1-methoxy-4-prormnyl benzene.
Minfy character Llnalool oxide and camphor.
Wocdy character p Caryophyllene, bnalyl acetate, terpinen-4-ol and myrisficin.
Waxy character Alcohols C-10 through C-12 and Citronellol.

“Listed In order of their importance to the aroma profile.

““It should be noted that commercial grades of many chemicals are not sufficiently pure. As a consequence, a clean fresh citrus
character CannOt be easily achieved synthetically.

61Perfumer & Flovorkt Vol. 15, 5s@emlmr/Ocmber 19%

 F Spice hbtesin Perfume~Y
L I

Group Ilk Spices with complex components.

Hydrocarbons Alcohol Aide.hydes Ketone Acid Ester ❑ase Sulfur Misc. Total
number
of
components
Ambrette Seeda 9“ 10 9 2 3 10 — — 1 44
Ambrettolide and
hydrocarbons

Angelica Rcd 15 2— 2— l—— 3 23

Hydrocarbons and
ketones

Calamuss 24 12 — 16 — l—— 3 56
Furfural, 5-methyl.2
-furfural, methyl eugenol

Cardamone 33 28 16 1 3 24—— 7 113

Eucalyptol and terpinyl
acetate and aldehydes

Carrot Seed7 35 14 7 5— 4— — 9 74
Hydrocarbons, y-
decalactone and
coumarin

Celery Seed 14 l— — — — — — 2 17
Hydrocarbons, 3-n-butyl
phthalide and related
phthatides

Corianderg 30 45 22 19 26 18 15 3 25 203
See Table I

Elemi10 93 6— — — — — — 1 1C4
Hydrocarbons particu-
Iarly a-phellandrene

Gnger’f 4s 25 13 10 3 7 — 3 12 121
Aldehydes especially
aldehydes C-3 through
C-8 and citral

Nutmeg12 26 20 3 2 6 9 — — 14 82
Eugenol, safrole and
phenols along with
hydrocarbons

Parsely’9 33 5 3 l— 2— 3 11 56
Hydrocarbons, cis-3-
hexenol, trans-2-
hexenal, cis-3-hexenyl
acetate and sulfur
compounds. (Methyhhic-
methane, carbondisul fide,
methyl dithiomethane)

quiterpenes or sequiterpene products have some- strong and characteristic aroma of black pepper that
what of a black pepper aroma. Although weak, these elutes at the point where the hydrocarbons end and
products are almost always complex mixtures and it is eucalyptol begins.ls
always difficult, if not impossible, to determine
Conclusions
where this characteristic aroma is coming from. It is
probable that the characteristic aroma of black pep- As can he seen from the preceding information,
per has something to do with the terpenes/sesquiter- perfumers have an impressive library from which to
penes or related compounds, They may be oxygen- draw and create new combinations of spice blends.
ated or contain a sulfur or nitrogen moiety or both, There is an additional aspect to consider, as in cook-
When a class separation is done on black pepper ing, there are many combinations of spices that may
and passed through a silica gel column there is a he used in a single fragrance theme. These odor types

Vd. I 5, se@emtBdoctotmrIm Perhm-er & Flavc.rist/7

I Spice Notes in Perfumery I
Group IV Spices with extremely complex components.

(Bark) (Fruit) Black (False Pepper)

Component Cascarilla Cubsb Peppa Schinus Molle
(Ref. 14) (Ref. 15) (Ref. 1S) (Ref. 17)

a-pinene 5.1 2.2 9.0 2.7

a-Thujone 2.8 — — —
a-Thujene Tr Tr 1.8 0.2
Camphene 1.0 — 0.1 1.2
~-pinene 0.9 — 10.4 0.4
Sabinene — 4.6 19.4 0.4

8-3 Carene — — 5,4 Tr

a-Phellandrene — — 1.7 5.3
a-Terpinene — — 0.3 Tr
p-Phellandrene — — 4.0 7,2
+ 1,8 Chad . 0.7 — —
Myrcene 3.6 — 2.0 5.3

Limonene 2,3 — 17.5 8.4

para Cymene 13.0 — 1.3 11.5
y-Terpinene 0.9 — 0.5 0.s
Linalool 2.7 — 0.5 0.3
Terpinens-4-ol 0.6 . 1.0 0.5
a-Terpineol — 2.2 — 1.0

1-Sorneol 2.5 — — —
Eugenol 0.2 — — —
p-Caryophyllene 9.0 3,7 14.7 0.3
Humulene — 4.9 0.2 3.0
&Cadlnene 3.7 8.8 0.5 6.S
&Bisabolene — 1.5 2.0 —

Copaene — 0.4 0.5 0.4

Cubebol — 10.0 0.1 2.4
Nerolidol — 3.5 — —
&Cubebene — 11.0 — —
Al lo aromadendrene — 4.2 — —
Calamenene — 3.7 — 0.3

may not necessarily be related. Vanilla can be a main due to geographic origin as well as different types of
theme and can be accented with basil. thvme or am extraction techniques.
combination of spices. There are no creative boun- To understand ‘many uses of spice and the effects
daries, only paths. that can be achieved requires many lifetimes of work
Further, there are many qualities of each of the and study. Regrettably, I only have one lifetime to
prececkng oils mentioned. In the clove family for ex- donate to this fascinating and exciting work but it has
ample, we have Clove Bud, Clove Stem and Clove proved to be an extremely rewarding and enjoyable
Leaf. All of these are available with varying qualities experience,

References

Address correspondence to Felix Buccellato, CuStOm Essencs S. Formacsk k Kubeckza, Essential 011sAnalysis by GC & Carbon
Inc., 67-1 OA Veronica Ave., Somerset, NJ 08873 USA. ‘$NMR, J W!ley & Sons, NY (1962)
9. MJM GijtMls, Phthalldes in Umbslliferae, PhD Thesis, Univer-
1. Freeman & Whenham, A Survey of VOlati10 components of sity of London, Netherlands, (196S)
some Alllum species in terms of S-alk(en)yl-L-Cystelne Sul- 10.0 Lamparsky, Pert& Flab’13(5),17(1936)
phoxides present as flavor pfacursors, J Sci 8 Food Agd 26, 11. Brleskorn& Krass, Olmarlcalpha Phellandrenes& FurlherTer-
1s69-1886 (1975) pnes, lXth InternationalCongressof EssentialOHS,Singapore
2. D Lampsrsky and I Klimos, Heterocyclic trace Components In (1963)
the Essential Oil of Coriander, Psrf & F/av 12(5), 17-25 (1986) 12. Maarse, TNO Volatile compoundsInFwd(1987)
3. Felix Buccallato, Unmtblished work in Progress (1969) 13. Maarse, 7N0 volatile compoundsinFcod(19S3)
4, El Lawrence, Perf & F/av 7(2) (1982) 14. Ibid (196S)
5. Ibid, 11(3) (1986) 15. Felix ❑uc%ellato, Unpublished work in progress (1969)
6. ❑ Toulemonde, Flav & Frag J 2,123-127 (1967) 16. BM Lawrence, Perf & Flav 5, (OctlNov. 1980)
7. B Toulemonde, Composition of Carrot Seed, Parfum Cn.?met
Arom 77, 65-69(19S7)
17. BM Lawrence, Psrf & F/av 10(2), 52 (1965)
18. Private communic9t10n from Dr. Brian Lawrence 1+?4
WPetir & F1.avorist Vol. 15, 59pte*er/CkfOtmr I 9$U