Perfumery Notes

Gardenia in Perfumery

By Danute Pajaujis Anonis, Consulting Chemist Perfumer, Forest Hills, NY

amed after Dr. Alexander Garden, an 18th (firm. Rubiaceae) originated in equatorial and
N century Scotiish naturalis~ the gardenia is South Afi’ica
a latecomer to perfumery, lbllowing jasmi% rose,
and violet.’ Gardenia flower oil was used in fra- Mode of ProductIon, Yield, end Type of 011
grances in the early part of the 20th century. In the beginning of the century, gardenia was
Today gardenia flower oil is scarcely produced, cultivated in Reunion Island. As in the case of
and synthetic compounds are used more often. other delicate flowers, steam distillation of gru-
denia flowers does not give any results. In the
Sotanlcal Origin past en fleurage was used, snd on extraction with
Many species of gardenias grow in various alcohol numbered infusions were obtained,s
parts of the world, particularly in the Far East. It giving on evaporation of alcohol concentrated
was reported that gardenias grow well in the extracts of pomade lavages. A more modern
Chungking region in Chin% where tuberose and method of extraction was the use of volatile sol-
osmanthus are also cukivated.z In Japan, Gat-- vents, re suiting in concrete oils and, on treat-
denia jasminoides is widely distributed. Gar- ment with alcoho~ absolutes.
denia grandiflom Lour and Gardenia jlorida L. Using petroleum ether as solvent, 3000 to

Vol. 8, October/November 1983 0272.2656M310005-31 O1$I24,O3IP 1$%3Allured PublishingCorp. PerF.mer & Flavori8t/31
 (found in nature only in lilac flowers).
Lilac aldehyde, phenylacetaldehyde, and an
unusually large percentage of jasmin lactone
were among other identified components.
4000 kilograms of flowers were required to ob- Among the more unusual cis-3-hexenol de-
tain one kilogram of concrete which yielded 0.5 rivatives, was cis-3-hexenyl cis-3-hexenoate
kg of the absolute, Naves and Mazuyer reported which was reported to be of a powerful green-
that 2 to 2,6 metric tons of flowers were required bamboo odor.
to obtain above quoted amounts of concrete and In the second study, alpha famesene and cis-
absolute oils.A jasmin hwtone were identified, and sixty other
In more recent experimental research work, components were confirmed in gardenia abso-
2.5 kg of Gardeniajasminoides, Ellis var. Hara Iute.s In the same study, tbe headspace gas was
flower petals were immersed in acetone for analyzed, and seventy components were iden-
three days, the extract was filtered and concen- tified in the gardenia flower volatiles. Among
trated to one-tenth of its original volume, and them beta ocimene, linalcml, cis-jasmin lactone,
then further extracted with n-hexane,s 400 mg of methyl, ethyl, cis-3-hexenyl, n-hexyl, benzyl,
concrete was obtained, yielding on alcohol ex- beta phenylethyl, and cinnamyl tiglates were
traction 250 mg of the absolute. considered to play a role in the gardenia odor.
Table I shows the main components of gar-
Composition denia absolute and the headspace gas identified
In the first decade of the century, the follow- in the first and second studies.
ing components of natural gardenia flower oil
obtained by maceration in paraffh were known :E

Benzyl acetate
Linalool
Table L Main Components of Gardenia Flower Oil
Linalyl acetate
Methyl anthranilate
S@dkl acetate (methyl phenyl mrbinyl acetate)
Terpineol
Ti2%&ai (w%%,,
Benzyl acetate was found to be present in the ........ GWde.ia “e.?dapam
Identified C.mwne.t, ~ Absolute 11 Gas
largest amount, but it was styrallyl acetate which % % %
was most suggestive of gardenia odor. .I,ha-,ar”e,me ,8.0 ,2., 2.2

In 1924, additional components were known:r Llnaba, 12.0 7.5 24.6

ol,-3-HexenY1 ti.late ,0., 3.1 3.1
.,,-.la, mti 8.0 ,7.0 6,
Acetic acid ,..,0”.

Be”mic acid .,,.3 -“.,..,1 ,8.,..,. 5.0 4.6

Lactone (C,, H,, O, ) beta C&me”. ,.u[trms) 0.2 45.8

Tiglic acid .,s-3 -Hex
... 1 , .0 ,.2 0.,

Methyl b+. . . . . . , .0 0.8 6.4

More recent research was done in Japan on “em t,,kte 1.0 0.5 , .7

Gardenia jasminoides E Uis oar. Hara using a

combined GC/MS, gas chromatography, IR and
NMR. In one study, 130 components were iden-
tified in gardenia absolutes No nitrogen-
containing components were included because The comparison of components in both
the basic fraction was too small for analysis of studies in Table I shows that alpha famesene,
such compounds. linalool, cis-3-hexenyl tiglate, and cis-jasmin
The following compounds were found to be hwtone are the main ingredients of gardenia ab-
the basic constituents for the gardenia odor: ben- solute, but their propofiion is different,
zyl, cinnamyl, cis-3-hexenyl, and 2-phenylethyl Beta ocimene and linalool are shown to be the
tiglates, cis-3-hexenol and its esters with C,+ main components of the headspace gas.
aliphatic and aromatic acids, linalool oxides, In reference to Table I, an observation may be
rose oxides, and four isomers of lilac alcohol made regarding benzoates. In the headspace gas

32/Pwfumer & Flcworist Vol. 8, October/November 1983

 164 Benzyl salicylate
180 Aldehyde C-18
120 Aldehyde C-14 p“r~
110 Linalool
100 Benzyl acetate
90 Methyl salicylate
a significant amount of methyl benzoate is pres-
70 Terpimml
ent, while in the absolute comparable amounts 60 Linalyl acetate
of cis-hexenyl benzoate are found. It may be 64 Petitgrain
pointed out that styrallyl acetate (methyl phenyl 60 Geraniol
50 Musk ketone
carbinyl acetate), which was found in the early 42 Tcdu resinoid
part of the century, mentioned before, in gar- 30 Phenyl ethyl alcohol
22 A“rantiol
denia absolute obtained by maceration, was not
10 Isoeugenol
identified in the headspace gas or gardenia ab- 5 Ethyl vanillin 10%
solute in either of the above studies.
Another gardenia type, containing styrallyl ace-
Synthetic Compounds tate:
In the past, styrallyl acetate combined with
Gardenia G-3
hydroxy-citronellal and small amounts of alcohol
200 BenzYl acetate
C-9, or phenyl ethyl heptylate was considered as 80 .4mY1cin”amic aldehyde
a base for gardenia. 10 In some cases, styrallyl 80 Phenyl ethyl alcohol
70 Ykmg ylang
acetate was combined with dimethyl benzyl
50 Linalyl acetate
carbinyl acetate. so Cyclamen aldehyde
Styrallyl acetate remains an important ingre- 50 Styrallyl acetate
40 Terpineol
dient of synthetic gardenia compounds. Ba-
40 Musk ketone
sically, styrallyl acetate combined with jasmin, 40 Orange sweet
rose, lily of the valley, lilac, and a small percent- 40 Cinnamic alcohol
30 Ethyl va”illin 10%
age of orange flower or their components will
30 Isoeugenol
produce gardenia odor characteristics. Some- !20 Methyl anthranilate
times woody notes and methyl ionone are 20 Li”alool
20 Anisic alcohol
added. Aryl carbinols or salicylates are used to 20 Tolu resi”oid
round out the harshness of styrall yl acetate. 15 Aldehyde C-8 1%
Linalyl benzoate and phenylethyl anthranilate 10 Indol 10%
are sometimes included in the formul% and al-
dehyde C-14 and C-18 are added as modifiers. Besides older established aromatics, modem
Aldehydes C-8 to C-12 are used for the top gardenia compounds may include more recent
notes, as are citrus oils, bergamot, orange, lemon synthetics, Among the former, isoamyl benyzl
and mandarin. Among conventional fixatives are ether, also called “Gardenia oxide,” of a mild
heliotropic, coumarin, musk ketone, cinnamic floral odor, blends with the harsher notes of al-
alcohol, labdanum, myrrh and tolu re sinoids. dehydes in a manner similar to the carbinols. ”
The new synthetic ambergris compounds are Phenyl ethyl cinnamate, anthranilate, and
valuable modern fixatives which enhance the salicy late are useful components in gardenia.
floral-green notes. Linalyl isovalerate contributes a citrus-fruity top
Some gardenia compounds of the past were note, Methyl octine csrbonate used previously
built on a tube rose note; they did not contain in some gardenia formulas can now be replaced
any styrallyl acetate, Aldehyde C-18 (nonalac- with the more modem nonadienol and its de-
tone) was used in such types which were suit- rivatives.
ah le as cream fragrances. Hydroxycitronellal is now mostly replaced by
Let us look at a few conventional illustrative more stable cyclamen aldehyde derivatives, or
formulas: other hydroxycitronellal substitutes. Cinnamic
alcohol and isoeugenol are used in limited
Gardenis G-2 (with a tuberose note) amounts because of dermatological consid-
3S0 Amyl cinnamic aldehyde erations.
200 Hydmxycitrcmellal
7.00 Benzyl alcohol Among newer aromatics, 2-ethyl hexanal CYCIO

36/PwF.mer & Flovorist Vol. 8, October/November 1983

 Absolute gardenia was used in the past in lux-
ury fragrances, It was also used as a modifier in
rose and other floral bouquets,
Gardenia has been used in brilliantines,
glycol acetate of a strong green-tart odor, linalool creams, lipsticks, powder, and soap. Today, gar-
oxide, rose oxides, hexenol and its esters, espe- denia compounds are also used in cosmetic,
cially tiglates, benzoates, and caproates, and toiletry, and soap fragrances, but mostly as com-
cis-jasmin lactone may be mentioned. Methyl ponents of a perfume adapted to the line, In
phenyl ethyl ether of a diffusive jasmin-rose powder fragrances, phenyl ethyl cinnamate is
note is effective in traces. used to advantage in gardenia, as it imparts
sweetness and is a good fixative.
Application A modern source describes the use of
In the beginning of the century, Chanel intro- homogenized gardenia oil in non liquid air-
duced a perfume named Gardenia Chanel, but it freshening compositions, using “ultra-amylo-
did not prove successful. Pungent florals came pectin (I) or starch carboxy methyl ether in ethyl
into vogue in the 30s, and several gardenia fra- alcohol, ” the mixture being further homoge-
grances were created. Among them, Jungle Gar- nized with wax m waxlike materials or paraffin
denia was a success, and it remains on the mar- and soaked in polyurethane foam, IS
ket, Gardenia was also used as a lotion fragrance
in the past, In today’s perfumer’s workshop, a Conclusion

gardenia fragrance is offered among other single Gardenia compounds are being modernized
flower perfumes. by the application of new aromatics, and by re-
A study made by the author in an enviro- placing dennatologically unameptable compo-
nmental exhibit in the Museum of Crafts in New nents.
York showed that a gardenia odor elicited a Fragrances have become more sophisticated,
highly favorable response in both under 25 and and today very few single floral gardenia per-
25-45 age female and male groups.lz The 25-45 fumes are created.
female age group showed a marked preference Gardenia plays an important role as a fra-
for gardenia over rose, lily of the valley, or grance modifier both in traditional and modem
orange blossom. fragrances, and it will remain a valuable floral-
Although gardenia is considered a secondary green note in future fragrances.
floral in perfumery, it plays an important role in
fragrances as a modifier. According to a noted Rafarances
French perfumer, the original Chanel No, 5 1.The American Heritage Dictionary of the English Language,
Houghton, Miffhn Co., Boston, 1978.
perfume contained a gardenia note. M
2. Chkang Hsi-Chang, Amer. Perf .Arom., 71(4), 31-34, April
Cot y’s f’Aimant contained styrallyl acetate 1958
used in jasmin, cassie and tuberose infusions 3. R. Cerbelaud, Formulaire de Parfumerie, Ed. Opera, 1951,
when the perfume was first created. 70.
4. E. Guenther, The Essential Oils, 0. Van Nostrand Co., New
The addition of gardenia to chypre resulted in York, 1952,5,355.
Crepe de Chine. A further development was Ma 5. T. Tsuneya, N. Ikeda, M. Shga, and N. Ichikawa, 7th Intl.
Cong. Essen. 01s, Kyoto, Japan, 1977
Griffe, an aldehydic chypre with a gardenia
6. Guenther, 5,356
note. 7. R. Tsuchihashi, and S. Fu)se, Taikoku ken Kouhou 4, 115
Among other established and more recent (1924)
8. R. Hattori, S. Murak, and T. Yoshida, 7th Intl. Cong. Essen.
perfumes containing gardenia or its components
Oils, Kyoto, Japan, 1977
are: Aphrodisiac, f’Air du Temps, Shocking, Vent 9. T. Tsuneya, N. Ikeda, M. Wig% and N. Ichikawa, Ibd
Vert, Cabochard, Detchema, Charlie, C aldche, 10. Cerbelaud, 74
11. E. S. Maurer, Perfumes and their Production. United Trade
Aliage, Michelle, Adolfo, Tatiana, and Premiere.
Press, Ltd., London, 195S, 277
In the 70s, the gardenia note came to prom- 12. 0. Pajaujis Anonis, Cosmet. Peti., 90(12), 48-50, Oecember
inence, and it was used to advantage in modem . .
1 Q75
13. M. Mllot, Amer. Perf. Cosmet., 81(4), 51-56, April 1966
green and aldehydic fragrances.
14. Maurer, 76
Gardenia-carnation-lavender are considered 15. G. Vayda, M. Vayda, Zarboch, Tibor, Hung.
osmically balanced floral components. 1A Halasztotl 0921 (Cl. C 116) 28 Sept. 1972 !4?

Vol. 8, October/November 1983 Perfumer & Flovcwist/37