Professional Documents
Culture Documents
EO1995 2000 Lawrence - 0004
EO1995 2000 Lawrence - 0004
EO1995 2000 Lawrence - 0004
& Flavorist,
fromPerfumer
Reprinted 1995,Vol.20, No.1, P. 47
JanuarylFebruary
c[-prnene 13.61 24.50 25.78 30.67 11.98 22.85 25.25 27.72 o-pinene(30.67%) camphor(6.35%)
campnene 4 .02 6. 91 6. 13 7. 01 7. 28 4.72 5.29 5.73 camphene(7.01o/o)linalool(2.69%)
B-pinene 1 .95 2. 04 4. 59 3. 61 2. 07 1.17 2.76 2 . 3 'l B-pinene(3.61%) bornylacetate(4.43%)
myrcene 2 j3 2. BB 2. 75 3. 15 4. 70 3.45 1.84 2.40 myrcene(3.15%) B-caryophyllene(0.97'/.)
limonene(3.83%) (0.99%)
cxterpineol
limonene 1.94 2.94 2.74 2.83 4.47 3.55 3.56 3.71 (1'1.04o/o) borneol(2.04%)
1,8-cineole
1,8-cineole 5.32 7.66 12. 81 t 1. 01 8.97 6-77 19.81 17.31 y-terpinene(0.67%)verbenone(5.72%)
v-f6rh ;na n6 I Rn
o.44 0.66 0.67 0.91 0.62 o.72 2.07 p-crrn9!9(t) geraniol
(1.020/4
p-cymene 0.51 0.73 tt 0.75 0.61 0.87 1.01
t=trace (<0.01%)
camphor 5.80 8.94 6.57 6.35 7.98 9.66 8.30 8.25
linalool 2.OS 2.81 3.00 2.69 0.51 2.60 4.33 4.27 A. Bayrak and A. Akgul, A study on the
bornylacetate 2.76 3.30 7.07 4.43 2. 84 1.90 1.84 1.75 composition of the essential oil tf rosemary.
B-caryophyllene1.06 1.44 1. 74 0. 91 0. 16 1.19 1.17 1. 0 3 Gida Sanyii,r(5),20-22 (1988).
cr-terpineol 0.85 1.09 1. 57 0. 99 1. 47 1.51 2-55 1.75 P. L. Cioni, G. Flamini and I.Morell|Indagine
borneol 4.14 5.00 2.37 2.04 10. 11 B-24 9.09 8.87 preliminare su una coltiaazione di Rosmarinus
verbenone 6.46 6.91 6.80 5.72 6.43 5.94 7.48 5.77
geraniol fficinalis in Prouincia di Pisa: Caralterizzazione
t t 1. 09 1. O 2 0. 92 1.55 1.44 1.13
dell'olio essenziale.RivistaItal. EPPOS, (3), 3-
6 (1991).
M. Jain,R. Banerji, S.K. Nigam, J.J.C.Scheffer
p-cymene(2.8%) (1.9%)
o-terpineol and H. C. Chaturvedi, In aitro production of
(0.2%)
terpinolene borneol(1.8%) essentialoil from proliferatingshootsof Rosmarinusfficinalis.
lenchone(0.37") PlantaMed.,57,122-124 (1991).
P.Kreis,D.Juchelka, C. MotzandA.Mosandl,Chiraleinhaltsstffi
In the analysis on the non-polar column, tricyclene ritherischert)leIX. Stereoclffirenzierungoonborneol,isobonteol
(0. unclbornyI acetate.D eutsch. Apoth.Ztg.,13 1, I I I 4-I I 87( 1991).
' -: and caryophyllene oxide 1 7o) were alsoidentified.
--, in 1993, Chalchat et al. compared the chemical K. P. Svoboda andS.G. Deans,A study of theuariabiliq of rosemary
:-ion of variousrosemary oilsof Moroccan, Spanish and sageand their uolatile oils on the British market; Their
- -:,cfi origins using GC/MS, A summaly of the oils of antioxidantpropefties.FIav.Fragr.J.,7,81-87(1992).
P. SanchezGomez, M. SorianoCano, ]. A. SotomayorSanchezand
E. Correal Castelianos, El Romero en la Region de Murcia, Table Vlll. Comparativechemical composition (%) of
Agricola Vergel (July), 444-449 (1992). Moroccanand French rosemary oils
S. Cataiano,P. L. Cioni, G. Flamini and I. Morelli. Stucliodella,resa
Compound Moroccanoils (7)a Frenchoils (3)a
e dellu composizione chimica di oli essenzialiottenuti cla planta
intera, rami efoglie confiort di Rosmarinus fficl,?zlis. Rivista Ital. tricyclene 0.10-0.23 0.24- 0. 41
EPPOS,(1 0),1 7- 19( 1993) . o-pinene s.56-12.72 19,91- 35. 08
crthujene 0.00-t 0.00-0.08
P. L. Cioni, S. Catalano,G. Flamini and I. Morelli, Indagine su una
camphene 3.21-3.98 5.86-8.35
coltiuozione di Rosmarinus tfficinaLis L. in proaincia dl pisa:
Studio della xariabilita della re,sae della cotnposizione chirLica B-pinene 5.53-7.83 2.08-4.35
d,ell'olio essenziale.Rivista Ital. trppos, (9), 3l-33 (1993). sabinene 0.14-0.21 0.21- 1. 36
6,6-dimethyl[3.
1.1]bicyclo-
Anon, Anahltica,l Methorls Committee, Application of gas-liqticl hepf 3-ene-2-butylene* 0.00-t 0.07-0-78
chronatography to the analqsis of essential oils. Paft XVL 6-3-carene 0.15-0.20 0.1 9- 1. 19
M onographsforfia e es,sential olls. Analyst, I I 8, I 089-1098 (I 993).
myrcene 1.27-1
.60 1.55- 2. 12
J. C. Chalchat,R. P. Garry, A. Michet, B. Benjilali and J. L. Chabart, oterpinene 0.52-0.66 0.39-0.46
Essential oilsof rosem,nry(Ro,smarimtsfficinalis L. ). Thechernical limonene 1.86-2.06 3.02-3.96
composition of oils of oarious origins (Morocco, Spain, France). !. 1,8-cineole 43.53-53.48 5.30-24.79
Essent.Oil Res.,5, 6f3-618 (1993).
(Z)-B-ocimene 0.00-0.27 0.00-0.05
B. M. Lawrence and C.-K. Sht, Essential oils as component,sof y-terpinene 0.93-1.19 0.2 8- 1. 28
mixtures: Analgsis and dffirentiation. In: Flaaor Measurement. (E)-B-ocimene 0.00-0.06 0.02-0.53
Edits., C.-T. Ho and C. H. Manley, pp 267-328,Marcel Dekl<er, p-cymene 0.99-1.40 1.3 9-
1. 54
New York (1993).
terpinolene 0.29-0.36 0.5 1- 0. 78
F. M. Soliman,E. A. El-Kashoury,M. M. Fathy and M. Il. Gonaid, frans-sabinenehydrate 0.04-0.1
I 0.0 9- 0.21
Analysis ancl biological actiaity of the essentialoil of Rosm,arinus viridiflorene 0.00-0.12 0.0 6- 0. 15
fficirtolis L. frorn Egypt. Flav. Fragr. J., 9, 29-33 (1994). camphor 7.42-10.80 3.0 1- 7. 50
S. Perrucci, F. Mancianti, P. L. Cioni, G. Flamini. I. Morelli and G. isopinocamphone 0.04-0.13 0.06-0.58
Nlacchior, In oitro antifungal actiuity of essential oilsagainst some linalool 0,73-1.76 1.4 6- 9. 41
isolateso;fMicro,sponrm canis and Microsponrnt gypseum. Planta linalylacetate 0.00-0.02 0.00-5.52
Med., 60, 184-187(1994). ct-santalene 0.00-0.80 0.00-t
bornylacetate 0.12-0.86 1.19- 14. 32
Laurel Leaf Oil 2.41-4.32
B-caryophyllene 0.0 0- 2.I 1
A sample of laurel leaf oil, which r,vasproduced by steam terpinen-4-ol 0.69-0.91 0.0 0- 1. 21
geranylacetate 0.00-0.07 0.33-0.68
distillation of the dried leavesof Laa rus nobilis of Albanian
origin was analyzedby capillary GC (Borgeset al. 1992).The tI-numutene 0.27-5.43 0.00-0.94
qualitativeand quantitativecompositionof this oil is summa- lavandulylacetate 0.00-0.30 r-0.54
rized as follows: B{arnesene* 0.37-0.51 0.00- 0. 19
lavandulol 0.00-0.23 0.00-0.06
a-thujene(0.3%) terpinen-4-ol (0.9%)
verDenone 0"00-0.46 1.0 3- 5. 08
o,-pinene(2.2o/") o,-terpineol (1.2%)
O,-terpineol 0.00-2.46 0.00-0.09
camphene(0.2%) ner ol( 0. 1% )
sabin en e(1 1.8 % ) borneol 3.00-4.51 3.24-6.53
Iinalylacetate(0.6%) germacrene D 0.00-0.1
3 0.00-t
B-pinene(2.4%) bornylacetate(0.4%)
myrcene(0.2%) eugenol(18.5%) y-muurolene 0.00-0.13 0.00-t
0,-phellandrene (0.2%) a-cubebene(0.2%) B-bisabolene 0.06-0.13 0.00-t
6-3-carene (0.1%) s-copaene(0.1%) cI-caornene 0.08-0.98 0.00-0.08
oterpinene(0.4%) methyleugenol (2.5./.) 6-cadinene 0.18-O.77 0.00-0.07
p-cymene(0.4%) (0.6%)
B-elemene
limonene(0.8%) B-caryophyl lene (1.1o/") nerol 0.00-0.10 0.00-0.05
'1,B-cineole(26.7%)
(E)-methyl isoeugenol (0.1o/o) 3,3,6-trimethyl[2"2.
1]
y-terpinene(0.6%) cr-humulene (0.2%) bicyclohept-1
-en-7-ol- 0.00-0.04
trans-sabinene hydrate(0.4%) eugenylacetate(0.1%) gerantol 0.00-0.05 0.00-t
terpinolene (0.2%) o- s elinene( 0. 1% ) caryophyllene
oxide 0.00-0.10 0.00- 0. 10
linalool(18.5%) B-bisabolene (0.1%)
cis-sabinene hydrate(0.4%) T-cadinol 0.00-0.11 0.00- 0. 12
6-cadinene (0.2%)
borneol(0.2%) thymol 0.00- 0. 18
elem ol( 0. 1% )
carvacrol 0.00- 0. 14
o-bisabolol 0.00-0.27
Also in 1992, Nigam et al. analyzedan oil producedins.\Vo
',ielclfrom the fruits of L. nobilis grown in India using GCIMS. t = trace (<0.01%)
anumberof samples
Trr,:conrpoundsidentifiedwere: *tentativeidentification
*correctisomer
not identified
crthujene(3.81%)
Table lX. Chemicalcompositions (%) of rosemaryoils a-pinene(9.30%)
of differentgeographicorigins sabinene(4.89%)
B-pinene(1.93%)
Compound Spain Morocco Tunisia Yugoslavia Portugal crc-phellandrene(10.07%)
1,8-cineole (28.37%)
o-pinene 19. 1- 35. 8 7.2-7.5 8.6-11.4 15.6-26.5 12.0-25.0 linalool(2.32k)
campnene 7. 0- 10. 0 4.3-4.6 2. 7- 4 . 3 3.2-8.2 1.3-1.9 camphor(2.17o/o)
B-pinene 3.0-7.7 4.9-5.0 2.7-7-7 0.7-2.0 1.5-3.4 terpinen-4-ol (1.39%)
myrcene 1. 1- 6. 0 cr-terpineol(5.85%)
0. 1 1. 1- 1 . 3 1.3-1.9 19.5-52.1
neral(0.61%)
limonene 2.9-5.0 t.z- t.o 1. 9- 4 . 8 2.2-3.3 2.4-10.6 geranial(0.67%)
'1,8-cineole 15. 0- 25. 1 + I. t- +J. I 40. 1- 5 5 . 1 18.5-39.2 4.2-5.6 cl-gurjunene (2.17%)
p-cymene allo-aromadendrene (0.85%)
0.4-2.4 2. 1- 2. 3 1. 1- 1 . 8 1.8-2.0 2.4-6.0
B-caryophyllene (3.33%)
campnor 6.6-20.7 11. 0- 13. 5 6. 4- 1 4 . 8 11.6-14.3 2.1-4.4 methyleugenol(1.16%)
linalool 0.5-2.0 myristicin(1.39%)
0.7-0.9 0. 6- 1 . 3 0.7-1-3 0.4.2.0
6-cadinene (0.07%)
bornylacetate 0.4-4.2 1. 0- 1. 1 o.4-1.2 2.4 0.5-2.0
The followingyear, Pino et al. (1993)
terpinen-4-ol 0.7-2.0 0. 5 0. 6- 1 . 6 0.1 1.8-6.8
compared the chemical composition
B-caryophyllene 1.8-4.3 0. 5 0. 9- 1 . 1 2.9-3.4 t
of laurel leaf oil produced from Alba-
oterpineol/borneol 2.0-5.0 2,9-3.2 2. 8- 1 5 . 9 2.8-6.6 1.3-4.1 nian dried leaf with three commercial
verbenone 0.5-6.0 I r t t-1.8 leaf oils of different geographic ori-
gins. The comparative data found on
t = lrace (<0.1 %)
Table XI describes only the composi-
tion of the three commercial samples
of laurel leaf oil. The composition of
the oil obtained from the Albanian
Table X. Chemicalcomposition (%) of Egyptianrosemaryoil
dried leafis described earlier.
This same year, Biondi et al. (1993)
Gompound Sinai oil Gazaoil Compound Sinai oil Gazaoil analyzed an olIof Laurus nobiliswhich
a-pinene 2.46 9.33 carvone 1.67 0.40 was produced from leaves collected in
camphene 1.63 3.65 cls-myrtanol 1.19 0.27 Sicily. The composition of this oil as
B-pinene 1.20 1. 80 frats-myrtanol 2.32 0.79 determined by GC and GC/MS was
myrcene 0.48 5.39 bornylacetate 7.59 1.98 found to be as follows:
P. Borges, j. Pino and tr. Sanchez, Isolation and chemical camphene 2.9 0.9 o .7
choracterizotion of laurel leaf oil. N ahrun g, 36, 494-496 ( 1992). sabinene 4.5 6.5 5 .2
M. C. Nigam, A. Ahmad and L. N. Misra, Laurus nobili,s:An
essential oil of potential aalue. Parfum. Kosmet., 73, 854-859 B-pinene 5.9 6.5 4 .9
(19 92 ). myrcene t.c 0.9 0 .7
a-phellandrene 0.3
J. Pino, P. Borges and E. Roncal, TLrcchemical composition of lourel
leaf oil frorn aarious origins. Nahrung, 37, 592-595 ( 1993). c{,terpinene t 1
4-vinyl-2-methoxyphenol benzoicacid
eugenol salicylicacid R-hicahnlana I I t
phthalide
5'-hydroxy-butyl phenylaceticacid 5-cadinene I 0.6 I
T GC/MS. They found that the oil contained the following 1-terpinene(20.0%) cuminaldehyde (25.01%)
i
i constituents: terpinen-4-ol (0.3%) p-mentha-1,4-dien-7-al
oterpineol (0.4%) (17.36%)
myrcene(0.3%) cuminaldehyde(21.0o/o) p-mentha-1,3-dien-7-al(5.84%)
limonene(20.2%) p-mentha-1 + p-
,3-dien-7-al e (0.20%\
B-caryophyllen
pentylbenzene(1.0olo) mentha-1 ,4-dien-7-al frans-0,-bergamotene(0.31%)
B-caryophyllene (1.9%) ( 1 e . 0 %)
B-selinene (15.9%) B-caryophyllene (0.3%)
cx-selinene (2.8%) B{arnesene-(0.4%)
butylphthalide(6.3%) carotol(0.6%)
cr-eudesmol + B-eudesmol 'correct isomer not identified
(1.8o/"\
senkyunolidea or isomer The fact that cuminaldehyde was not listed in the compo-
(37.3%) nents identified when the oil was analvzed on a polar column
aalso known as sedanenolideor butyl-4,5-dihydrophthalide r.ras probably a $.pographical oversighr by the jou rnal within
which the original article was found. It would be a strange
Itis unlikelythatthe characterizationofc,-and B-eudesmols
cumin oil if no cuminaldehyde was found as a constituent.
in celery seed oil at levels of L87o is correct. These com-
Also in 1993, Shaath and Azzo analyzed a sample of cumin
pounds are unusual constituentsof umbelliferous seedoils.
seed oil of Eg,ptian origin by a combination of GC/MS and
R. G. Berger,F. Drawert,H. Kollmannsberger andS.Nitz,Natural retention indices on two capillary columns of differing polar-
ocaffrenceof undecaenes j. Food
in somefruits and aegetables.
ity. The compounds identified in the oil were as follows,
Sci.,50, 1655-1656(1985).
cr-ihujene(0.28%)
R.ter Heide,P.J.deValois,D. de RijkeandA.A. Bednarczyk,Acids cr-pinene(0.78'/.\
and Phenolsin SeoenSpiceEssentialOils. Paperpre-sentedat camphene(t)
ACSmeeting,NewYork(April 13-18,1986). sabinene(0.40o/"\
B-pinene(14.640/0)
J.Verghese,
In theKaleidoscope:Celery.
Per{.& Fiav.,f 5(3),55-59 myrcene(0.52%)
(1eeo). o-phellandrene (0.63%)
p-cymene(4.91"/")
A. F. Halim, M. M. Mashaly,O. Salama,A. F. Ali and P. Sandra,
B-phellandrene (0.30%)
Analysis of celery fruit oil and inaestigation on the ffict of
limonene(0.37%)
storage.Egfpt. I. Pharm. Sci.,31, 107-113(1990).
y-terpinene(19.12%)
D. K. Choudhary and B. L. Kaul, Volatile aroma constituents of t=trace (<0.01%)
l0
I
cuparene, cedrol and the tr,vocadinols was tentative requiring identified
in the extract, they did characterize the following
independent corroboration before being fully acceptedas a compounds:
black pepper oil constituent. citronellal
a-pinene
Also in 1993,Hossainet al. comparedthe major volatilesof B-pinene B-caryophyllene
white pepper before and after the spice had been irradiated myrcene carvone
with y-rays. Although the authors found that the volatiles in limonene methyleugenol
p-cymene eugenol
white pepper did not show any significant changes,standard
volatile oils showedthat irradiation causeda marked decrease
K. Takahashi,S. Murah and T. Yoshida, Synthesisand distributiort, of
in 6-3-careneand limonene contents while the levels of cr-
(-)-mintsulphide, a noael sulfur-containing sesquiterpene. Agic.
pinene, myrcene and B-caryophyllenereportedly increased. Biol. Chem.,45, 129-131(1981).
As no statistical evaluation of this study was performed, the
results presented are suspectand require corroboration be-
fore thev can be accented.
More recently, Yasumoto et al. (1994) reported that the Table lV. Percentagecomposition of oxygenated
black pepper could be efficiently extractedusing liquid CO, sesquiterpenesin Muntok pepper oil and extract
at pressuresof 70-200 kg/cc at 20'C. When they introduced
ethanol (0.5-2.0Ea)into the extractingsolvent,the extraction Compound oi l Extract
efficiency towards piperine was increased.Although the au- isocaryophyllene
oxide I I
thors did not present any quantitative data on the volatiles caryophylleneoxide 0.2 0. 9
cr-humulene-1,2-epoxide I I
oxygenatedmonoterpenoidcompounds in spathulenol t
Muntok pepper oil and extract T-muurolol I
o-bisabolol I
Compound oil Extract
s-cadrnol I
1,8-cineole 0 .2 0.4
selin-11-en-4-oll I t
lrans-sabinenehydrate I I
cadina-5,10(15)-dien-4-olt 0.2 1. 3
fenchone I I
cls-sabinenehydrate I I B-humulen-1-ol t
linalool 0 .8 u.b caryophyllen-5-ol
I t
caryophyllen-5-ol
ll I t
a p-menthadienol- I I
caryophyllen-5-ol
lll i
lrans-p-mentha-2,8-dien-
1-ol I I
caryophyllen-5-ol
lV I
c/s-p-mentha-2,8-dien-
1-ol I I
4-5-epoxycarene I I i tentativeidentification
a-pineneepoxide I I t = trace(<0.1%)
frans-pinocarveol I I
campnor I I
trans-p-menthan-8-ol I I Table V. Percentage composition of some
prnocarvone I I miscellaneouscompounds in
m-mentha-1,3-dien-8-olt 0.2 0.2 Muntok pepper oil and extract
p-mentha-1,5-dien-B-ol I I
3-pinanone* I I Compound oi l Extract
terpinen-4-ol 0 .3 0.1 methylpiperinate t 0. 2
oterpineol 0.2 0.2 methylcitronellate 1 t
B-phellandren-6-ol 0 .1 0.2 linalylacetate t
a phellandrenol.t I I a terpinylacetatet t
1,4,4-trimethylcycloheptadienone- I I cxterpinylacetate 1
crs-piperitol T I
2-undecanone t t
l terpinen-5-ol I T
hanzaldahrrdo t t
a phellandrenol-i I t
p-cresol I t
carvone o .2 1 m-cresol t t
2-caren-3-onet I I
p-methylacetophenone t t
piperitone I I
3,4-methylenedioxystyrene t
3-caren-2-onei I 0.2
3,4-methylenedioxybenzaldehyde 0.1 0. 5
carvacrol t I
3,4-methylenedioxycinnamaldehyde 0. 2
* correctisomernot identified
t tentativeidentification I tentativeidentification
t = trace (<0.1%) t=trace(<0.1%)
11
J. Pino, G. Rodriguez-Feo,P. Borgesand A. Rosado,Chemicaland of GC and GC/MS in the El mode and C.I. mode, the oils and
sensory propefties of black pepper oil. Nahrung, 6, 555-560 extracts were analyzed, the results of u'hich can be seen in
(199 0).
Table VII. It is of interest to note that CHr-Cl, extract of the
H. Kollma nn sb erg er , S. Nit z and F. Dr awer t , U b e r d i e plants produced from the Vietnamese seed was richest in
Aromastoffzusamtnensetzungaon H ochdruckertrnkten LPfffir
(P\ternigrumaar. Muntok).Zeit. Lebensmitt. Untersuch. Forsch., arteannuin B, the antimalarial constituent of A. annua.
194, 545-55r (1992). In 1994, Chalchat et al. compared the composition of
French and YugoslavianA. annuo oil produced from plants
M. Gopalakrishnan,N. Menon, K. P. Padmakumari,A. jayalekshmy
harvested at different maturity stages.A summary of their
and C. S. Narayanan, GC analysis and odor profiles of four new
Indiangenotypesof PipernigtumL. j. Essent.Oil Res.,5,247-253 results can be found in Table VIII. The authors found that
( 1993). although the o,-pinene and artemisia ketone contents were
fairly similar in oils produced when the plants were haruested
H. Kollmannsberger and S. Nitz, Saureamidein Hochdntckertrakten
in the budding stages,the artemisiaketone content reacheda
aus Muntok-Pfffir. Chem. Mikrobiol. Technol. Lebensmitt., 14,
87-94(1se2). ma.ximumin plants that were hawested towards the end of the
flowering period. In addition, the oil content of plants in the
S. N. Hossain, Y. Watanabe and I. Ishigaki, Chemical changes in
budding stagewas 0.02-0.09Vowhile plants at full flowering
Jlat:oring com,ponentsin white pepper (Piper nigrum L.) due to
galmna irradiation. Bangladeshj. Sci. Res.,28(3), 76-84 (f 993). possessed an oil content of 0.15-0.437o.
D. j. Charles, j. E.Simon,Chmonerkationoftheessen-tialc,il
E.Cebeftand
M. Yasumoto, T. Okazaki, T. InaLrrma and T. Kobayashi, Extraction
oJ.Artemisiaannua L. l. Essent.Oi1 Res.,3, 33-39 (1991).
of pipe4ne and aolatile compoundsfromblack pepper u'ith liquid
carbon dioxide. Nippon Shokuhin Kogro Gakkaishi,4l, 102-107
(1ee4). Table Vl. Comparative chemaical composition of the
feaf and flower oil of Artemisia annua
t2
j. C. Chalchat,R. P. Garry,A. Michet, M. Gorunovicand D. Stosic,
TableVlll.Comparativechemicalcomposition(%)of
A contribution to chemotaronomll of Artemisia anrrua L.,
Artemisiaannuaof Frenchand Yugoslavianorigin
Asteraceae.Acta Pharm. Jugoslav.,41, 233-236 (1991).
harvestedthroughouttheir growthcycle
H. J. Woerdenbag,R. Bos, M. C. Salomons,H. Hendriks, N. Pras Compound Frenchoil Yugoslavian oil
and T. M. M alingr6, Volatile constituent s of Art emisia annua L.
(Asteroceae).Flav. Fragr. I., 8, 131-137(1993). tricyclene 0.01-0.35 0. 10
0-pinene 4.20-15.66 1. 25- 7. 00
j. C. Chalchat, R. P. Garry and J. Lamy, InJluence of harcest time a-thujene 0.00-0.90
on qield and composition of Aftemisia annua oil produced in bornylene 0.00-0.29
France.J. trssent.Oil Res.,6,261-268(1994). ethyl2-methylbutyrate 0.00-0.17 0.20-0.30
campnene 1.20-7.28 1, 50- 2. 45
TableVll.Comparative chemicalcomposition(%) p-pinene 0.93-3.35 0.20-1.10
of Artemisiaannuaoils and extracts sabinene 0.43-2.80
3-methylbicyclo-[3.1.2]-oct-2-enei
0.00-t
of differentseedorigins butylisovalerate 0.00-0.14
o,-phellandrene 0.00-t
Chinese seed Vietnamese seed myrcene 0.00-3.34
Compound oil CH2C|2 oil C H 2C | 2 cx-teroinene 0.00-0.18 0.00-0.14
exlract extract 2-oxa-bicyclo-[2.2.2]-oct-6-enet
0.00-0.1
5
limonene 0.09-0.57
artemisiatriene 0 .1 1,8-cineole 5.07-14.68 7 .5 0 - 1 1 .6 5
0,-thujene I I y-terpinene 0.07-0.34
cr-prnene o.4 0 .5 (E)-B-ocimene 0.00-0.27
campnene 1.0 2 .3
p-cymene 1-1.23 0.25-0.90
sabinene I I
terpinolene 0.00-0.33
B-pinene 0. 1 0.2 0. 1 0.4 artemisiaketone 11.91-55.02 37. 10- 52. 50
myrcene 3. I 2 .1 0.9 0.4 isovalerate 0.00-0.31
3-methyl-3-butenyl
yomogialcohol no 0 .4
santolinaalcohol t-0.22
yomogialcohol 0.06-0.64
p-cymene 0 .7 0.4
isopinocamphone 0 .1 I artemisiaacetate 0.00-0.07 0.15
frans-sabinenehydrate 0.00-0.43 0.05-0.45
'1,8-cineole I o-campholenic aldehyde 0.00-0.66
(E)-2,7-dimethylocta- cr-copaene 0.00-1.33 0. 10- 12. 30
camphor '|.58-11.52 1.70-10.90
4,6-dien-2-ol 0 .3
ademisiaketone 63.9 artemisiaalcohol 0.00-11.95 1 . 10-.170
y-terpinene (Z)-3-hexenylbutyrate 0.00-r
lrans-sabinenehydrate pinocamphone 0.00-0.32 0.05
B-cubebene o.09-2.17
artemisiaalcohol 7.5 5 .3 cls-sabinenehydrate 0.11-0.83
cls-sabinenehydrate 0 .5 0 .2 tt prnocarvone 0.24-2.19 0 . 05-.110
camphor 3 .3 4 .9 2 1.8 15.3 B-caryophyllene 1.63-10.87
cls-chrysanthenol 0 .3 0 .2 0 .5 t terpinen-4-ol 0.13-0.38
borneol 0 .2 0 .2 1 .3 0.2 myrtenal 1-0.42
3{hujen-2-ol"- 0.00-2.16
terpinen-4-ol 0 .5 frans-pinocarveol 0.35-1.81 l.oo-z.ts
cr{erpineol 0 .1 cr-himachalene t-0.97
p-myrcenehydroperoxide o-humulene 0.00-0.74
c(-myrcenehydroperoxide (Z)-B{arnesene 0.00-1 .10
bornylacetate o .t (E)-B{arnesene 0.00-1.00
rlerylacetate o .4 DOrneol 0.00-0.16 o.zo
aterpineol 0.00-0.65
trans-chrysanthenylacetate - 0 .3 0.2 germacreneD 1.99-18.54
cis-chrysanthenylacetate 0 .3 0.2 cI-guaiene 2.24-14.73
c{-copaene 0 .7 1.5
bicyclogermacrene 0.16-1.28
3-elemene 0 .2 0.1
frans-(3,3-di
methyl)cyclo-
3-caryophyllene 2 .5 0"5 c.o J, I hexylideneacetaldehydet 0.00-0.41
c{-numulene t 0 .3 o-cadinene 0.00-1.05
6,6-dimethyl[3.
1.1]-bicyclohept-
, E)-p{arnesene 1. 3 0 .3 3 .8 1.2
2-en-2-methanolr 0"08-0.67
germacreneD 1 8 .3 0.8
4. 7 0 .6 0.3 isocaryophyllene
oxide 0.04-0"39
caryophylleneoxide 0.10-1.64 0 . 10- 1. 90
-,€lemene t.J spathulenol 0.00-0.49
a cadinenol* 1a
0"3 nootkatone 0.00-0.82
a'leannuicacid t 1.8 cedrol 0.00-t
a'.ieannuinB o.z 14.9 thymol 0.00-0.83
a'iemisinin 1. 7 22.3 carvacrol 0.10-1.10
t = trace (<0.01%) t tentativeidentification
: = : r a c e( < 0 . 1 % ) * correclisomernot given a also knownas umbellulol
' :,crrectisomernot identified
13
Gi n ger O il o-copaene(0.7%)
linalool(0.4%)
Using a combination of GC/MS and retention indices, a bornylacetate(0.8%)
sample of ginger oil, which was produced from ginger grown neral(1.3%)
in Taiwan,was examinedby Sheenet al. (1992).Theseauthors b o r n e o(l 1 . 1 %)
identified the following constituents: zingiberene + geranial(29.0%)
B-bisabolene (5.8%)
o-thujene(0.21'/") neral(6.04%) o,-farnesene* + geranyl
cr-pinene(4.41%) zingiberene(2.84"/.) acetate(7.3%)
camphene(16.03%) geranial(18.95%) B-sesquiphellandrene (14.0%)
B-pinene(1.10%) B-sesquiphellandrene + ar- geraniol(0.4%)
myrcene(1.15olo) curcumene+ geranyl
lim o ne ne(1 .60 % ) acetate(12.32'/.)
B-phellandrene (6.79%\ citronellol(9.10%) From the analysis of the same oil on the non-polar column,
1,8-cineole (8.86%) nerol(0.05%) the oil was found to contain:
terpinolene (0.24%) geraniol(0.73o/o)
2-heptanol + 6-methyl-s-hepten-cubebolisomer*(0.03%) tricyclene(0.2%)
2-one (0.67%) o-pinene(3.0%)
cubebolisomer*(0.03./")
2-nonanone(0.07%) methylheptenone(0.4%)
a curcumenol* + unKnown
citronellal+ o-copaene(0.52%) sesquiterpeneestet(0.27"/o) B-pinene+ myrcene(0.7%)
2-nonanol(0.13%) B-phellandrene (9.6%)
elemol(0.26%)
linalool(0.80%) linalool(0.8%)
sesquisabinene hydrate.
(0.01%) (0.23'/") borneol(0.8%)
B-elemene
2-undecanone (0.36%) (0.3%)
o,-terpineol
zingiberenol (0.38%)
bornylacetate(0.26'/") nerol(0.2%)
p{arnesene*+ citronellyl neral(1.4k)
acetate(0.38%) geraniol(0.5%)
geranial(1.4%)
geranylacetate(0.9%)
The authors evaluatedthe odor strength ofeach compo- cx-copaene (0.4%)
B-elemene (0.7%)
nent at the exit port of the GC. They found that the main (29.0%)
zingiberene
contributors to the odor of the ginger oil under study were B-bisabolene + u-farnesene*
neral, geranial, B-sesquiphellandrene,ar-curcumene and (14.0%)
geranyl acetate. It is not sulprising that these authors be- 0-sesquiphellandrene (9.9%)
lieved that neral and geranialcontributed to the odor ofthe " correct isomer not identified
iected to analysis(Anon 1993) using GC/MS Compound Mother Central 1st 2nd 3rd 4th
anclKor-atsIndices on both a polar and a non- cx,-prnene 31.3- 34.6 22.3 31.7 38.5 4 1.1
polar SCOT capillarycolumn. The compounds campnene 120.9 168.9 102.6 105.2 1 3 5 .6 t r+ 3 . c
identified and the amounts that were found in myrcene 25.9 36.7 23.2 31.0 36.7 37.5
i l . p olar c olum n an a l y s i w
s e re : 50-2 38.4 22.2 42.6 75.7 92.6
B-phellandrene
l.icyclene(0.2%) 1,8-cineole 74.7 76.0 75.1 69.6 85.6 72.9
cr-pinene(3.3%) borneol 13-2 18.3 10.8 14.0 10.4 12.9
camphene (8.8%) neral 190.9 71.6 35.8 42.9 5 0 .3 5 3 .1
3-pinene (0.5%) geranial 295.1 211.9 278.8 294.4 330.1 362.2
sabinene (0.8%)
nyrcene(1.5%) geranylacetate - 4.6 7.9 25.3 59.9 6 4 .1
csphellandrene (0.5%) ar-curcumene 30.8 34.0 21.2 29.5 32.8 34.4
i rmonene+ 1, 8- c in e o(1
l e.7 % ) zingiberene 371.0 662"6 318.1 477.1 6 6 9 .1 723.3
3-phellandrene (8.2%) B-bisabolene 149.5 186.9 124.6 164.4 251"6 266.3
':.:erpinene(0.1%) p-sesquiphellandrene 19 0 . 5 229.9 1 3 1. 4 1 7 7. 3 2 5 6.3 268.4
;-cymene (0.1%)
::':lrolene(0.3%) - ppm
tified. This same year, Demissew (1993) reported that the a{hujene l i nal ool
6-methyl-5-hepten-2-one B-sesquiphellandrene
2-nonanone nerol
The following year, Denyer et al. (1994), reported that
citronellal geranyl2-methylpropionate
several sesquiterpenehydrocarbons such as ar-curcumene, ct-copaene elemol
zingiberene,B-bisabolene and B-sesquiphellandrene possessed
antirhinoviral activity (activity against rhinoviruses which are
among those responsiblefor the common cold), the latter of They found that three months after the ginger was irradi-
these being the most active. ated,the amountsof certain componentssuch aszingiberene,
AIso in 1994, Pellerin described the differencesbetween o-bergamotene,neral, geranial and ar-curcumenewere sig-
ginger oils produced from Z. fficinale grown in Australia, nificantly reduced over the same volatiles isolated from non-
India and Sri Lanka. These differencescan be seen in Table irradiated ginger.
X. It is a shame that the author didn't review the study of van This sameyear,Vernin and Parkanyi (1994) compared the
Beekand Leliveld ( 1991) becausehe would haverealizedthat major componentsof Chineseand Indian ginger oil using CC/
the main sesquiterpene hydrocarbons of ginger oil are as
follows: Table Xl. Comparativechemical composition (o/o)
of Chineseand lndian ginger oil
zingiberene
F-bisabolene
(E,E)-o,{arnesene Compound Chineseoil lndianoil
B-sesquiphellandrene cr,-prnene 1.30 1. 40
ar-curcumene camphene 4.65 4.46
Also, it should be noted that zingibene existsonly asa single B-pinene 0.17 0. 12
compound not in cx-and B-forms. sabinene 0.06 0.04
Wu and Yang (1994) compared the volatiles of ginger myrcene 0.57 0. 43
before and after treatment of the rhizomes with y-irradiation. 0. 23
o-phellandrene 0.15
The volatile compoundsthat were monitored by GC and GC/ limonene 0.95 0. 91
\IS were: 2.45 3. 41
B-phellandrene
1,8-cineole 2.07 1. 70
p-cymene 0.06
Table X. Comparativechemical composition
of various ginger oils terpinolene 0.16 0. 13
2-heptanol 0.04 0.36
Australian Indian Sri Lankan 6-methyl-5-hepten-2-one 0.35 0. 17
Compound oil oil oil 2-nonanone 0.02 0"41
camphene 13. 9 t 0.9-14.1 o-copaene t 0.46
p-bisabolene 20.1-60.4 B-elemene 1.15 0. 71
p-bisabolene+ B-farnesene* 2 .1 I t.c 2-undecanone 0.10 1. 43
ar-curcumene 5 .9 18. 9 5.7-27.1 cr,-terpineol 0.80 0.32
pJarnesene* 0.5-1.2 B-caryophyllene 0.50 0.30
p-sesquiphellandrene 3 .1 t-0.3 borneol 2.16 2.82
p-zingiberene 0.3-1.2 zingiberene 38.12 40.20
a-zingiberene 0.1-0.6 B-bisabolene 5.16 6.00
zingiberene 3 .9 7. 4 B-sesquiphellandrene 7.20 7.30
linalool t.3 1. 3 1.0-5.4 ar-curcumene 17.06 17. 08
nerolidol. 1A 1. 6 0.6-1.0 geraniol 0.66 0.50
p-sesquiphellandrol 1. 5 1. 6 0.2-1.2 nerolidol- 0.37 0.41
geranial 5.2 1. 0 1.8-15.3 cls-sesquisabinene
hydrate o.23 0.22
neral 4. O 0.6 2.5-10.1 zingiberenol 0.34 0.30
1.8-cineole 7.5 0. 3 2.1-12.2 trans-B-sesquiphellandrol 0.14 0. 16
: = t r a c e( < 0 . 1 % ) t = trace(<0.01%)
* correctisomernot given
'correct isomernot characterized
15
MS, the results of which can be seenin Table XI. Numerous In 1981, Takahashi determined that ylang ylang oil of
minor componentsthat were also identified were: Reunion origin contained germacrene D (4.67Eo)and mint
nexane aromadendrene sulfide (0.001E")as minor constituents.An oil of ylang ylang,
othujene (Z)-B-farnesene which was produced in Yunnan (China), was reported (Cu
toluene (E)-B{arnesene 1988) to contain the following components:
hexanal 6-selinene
2-heptanone neral cr-pinene (0.01%) (33.00%)
B-caryophyllene
octanal 6-cadinene B-pinene(0.02'/.) cx-humulene(7.69%)
p-isopropylanisole ar-curcumene p-cresylmethylether (2.41%) y-muurolene(19.82%)
5-elemene cis-calamenene methylbenzoate(0.660/0) a bergamotene.(5.40%)
cx-amorphene 2tridecanone linalool(0.41%) B{arnesene(3.29%)
R-nr rhahana germacreneB benzylacetate(0.05%) B-cadinene(1.74"/.)
campnor frans-calamenene
2-nonanol elemol
linalool frans-sesqu
isabinenehydrate
cis-limoneneepoxide 10-epi-y-eudesmol Table Xll. Comparativechemical composition (%)
frans-limoneneepoxide zingiberenol"
isomer of differentylang ylang oils
cls-o-bergamotene o-eudesmol
frans-d-bergamotene B-eudesmol Compound Yunnan Laos Thailand
y-elemene pentenylcurcumene*
(China)
cr-thujene 0 .1 3
0,-pinene 0.01 0.03 0.24
T. A. van Beek and G. P. Le$eld , Isolation and identification of the sabinene 0.26
fiae mojor sesquiterpene hydrocarbons of ginger. Phytochem. B-pinene o.ou o.tt 0.05
Anal.,2, 26-34 (199i). myrcene 0 .5 7
L-Y. Sheen, S-Y. Lin and S-j.Tsai, Odor assessmentsfor oolatile cr-phellandrene 0 .0 1
compoundsof gadic and ginger essentialoils by snffingmethod of 6-3-carene 0.06
gaschromatogrryhA J. ChineseAgric. Chem. Soc.(Taiwan),30, p-cresylmethylether 11.55 2.08
p-cymene 0.64
14-24 (1992).
1,8-cineole 0.01
M. Tanabe,M. Yasuda,Y. Adachi and Y.Kano, Seasonaloariation of
(Z)-B-ocimene 1 .4 5
Jlaaor components in Japanese "Kintoki Ginger." Shoyakugaku (E)-B-ocimene 1 .3 8
Zasshi, 46, 37 -41 (L992).
6-2-carene 0 .1 2
Anon, Analytical Methods Committee, Application of gas-liquid allo-ocimene* 0 .0 7
chromatography to the analysis of essential oils. Par't )l.y'l. linalool 3.28 10.64 6.62
M onographsfor fia e essential olls. Analyst, f f 8, I 089- 1098 ( I 993). methylbenzoate 1.O2
benzylacetate 0.28 0.13
S. Dernissew, A description of some essential oil-bearingplants in
Ethiopia andtheir indigenoususes.!. Essent.Oil Res.,5,465-475
terpinen-4-ol o.,o
o(-terpineol o.o7
( 1993).
methylchavicol 0.09 o.to
C. V. Denyer, P. jackson and D. M. Loakes,lsolationof antirhinoairal citronellol 0.02
sesquite:enesfrom ginger (Zingiber fficinale). l. N at.Prod., 57, geraniol 5.07 1.98 0. 01
658-662(1994). citronellylacetate 0. 02
P. Pellerin, Le gingembre: production et analyse. Parfum. Cosmet.
s-copaene 0"03 o.oa 0. 40
geranylacetate 13.41 13.68 0.30
Arom., (117),70-73(1994).
B-elemene 0.11 o.12
j-j. Wu andJ-S.Y utg,Effects of yirradiation onthe oolatile compounck 25.44 25.68 11. 39
B-caryophyllene
of ginger rhizome (Zingiber fficinale Roscoe). ]. Agric. Food q-humulene 5.54 6.48 2.83
Chem., 42, 2574-2577 (1994). y-muurolene 17.09 15.76 11. 38
s-larnesene* 6.39 4.76 38.72
G. Vernin and C. Parkanyi,Gln ger oil (Zin giber ffi cinaleRoscoe). h:
Spices, Herbs and Edible Fungi. Edit., G. Charalambous, y-cadinene 0.08 0.07 0.20
pp 579-594,Elsevier SciencePubl., Amsterdam (1994). B-cadinene 0.82 0.99 0.83
6-cadinene 0.03
elemol 0.02 0.05
Yl a ng Y lang O il
6-cadinol 0.31 o.22 i,,
farnesol* 3.41 4.69 8.39
In 1966,Vernin reported that ylang ylang oil contained methyl
benzylbenzoate 5.57 9.48 5.29
anthranilate as a trace component. Twelve years later, Ross farnesylacetate* 0.28 0 . 1I t.zJ
(1978)used reversedphaseHPLC on a H1)ersil SAScolumn benzylsalicylate 0.25 0.28
with methanol-water (1:1) as the mobile phase to separate dibutylphthalatet o.uu
methyl anthranilate, benzyl acetate and p-methylanisole in a * correctisomernot given
sample of ylang ylang oil.
16
methylchavicol(0.04%) farnesol*(4.75%)
geraniol(2.48%) benzylbenzoate(5.33%) Table XlV. Comparative chemical composition (o/o)
geranial(0.04%) farnesylacetate*(0.91%) of the different grades of ylang ylang oil
o-copaene(0.51%) benzylsalicylate(0.34%)
geranylacetate(6.21%)
Compound Extra ill
'correct isomer not given
isoprenylacetate o.74 0.42 0.04 0.01
It shouldbe noted that this oil is very atlpical forylangylang prenylacetate 1.59 0.89 0.08 0.02
oil. Based on the above-noted oil composition, it must be cI-pinene 0.23 0.19 0 .1 3 0 .0 8
presurnedthat the oil also possessedan atypical aroma. (Z)-3-hexenylacetate 0.14 - 0 .0 2
This sameyear, Ding et al. (1988) examinedthe composi- hav\rl r^al.+a 0.22 - 0 .0 1
tion ofylang ylang oil produced from three different sources p-methylcresol 8.47 5.75 1 .1 9 0 .3 9
br GC/MS. The origins of the three different ylang ylang
1,8-cineole
+ limonene 0.20 0.17 0 .0 9 0 .0 3
shrubs were Xishuangbanna(Yunnan), Thailand and Laos, methylbenzoate 4.97 3.35 0.70 0.20
altliough the ylang ylang flowers were all harvested from linalool 8.60 7.27 2.56 0.76
transplantedshrubs grown in Xishuangbanna.A summary of benzylacetate 12.36 7 "68 1.68 0.69
the analysesis shown in Table XII. cx,terpineol
+ methylchavicol 0.15 0.13 0 .11 0 .0 2
These same authors also compared the composition of 2-phenethylacetate 0.19 0.12 0 .0 4 0 .0 2
r lang ylang oil produced from the Yunnan ylang ylang from
geraniol 0.29 0.37 0 .4 3 0 .19
ilou'ers picked at different harvestingtimes. The oils, which (E)-anethole 0.36 0.19 0 .1 7 0 .0 9
lr ere produced from green buds, green flowers,green/yellow eugenol 0.08 o.20 0.29 0.06
ilou'ers and yellow flo'uvers,were found to possesscomposi- geranylacetate 4.48 4.26 2.96 1 .2 1
tior"raldifferences as shown in Table XIIL cr-copaene 0.61 0.81 1 .2 2 1 .6 0
In 1992, a commercial report appeared (Benvenisteand B-cubebene + B-elemene 0.41 0.49 0.64 0.54
-\zzo) within which the analysis of the four grades of ylang cinnamylacetate 3.97 2.76 1 .0 9 0 .8 8
riang oil produced in the Comoro islands (Federal Islamic isoeugenol* 0.50 0.50 0.29 0.36
Republic of Comores) could be found. The four commercial 5.18 8.04 12.90 12.39
B-caryophyllene
s-radesof ylang ylang oil are: Extra (first fraction, ca. I57o), B-cedrene 0.14 o.20 0.37 0.46
Crade I (secondfraction, ca. I57o), Grade II (third fraction, o-humulene 1.76 2.67 3.35 3.62
prenylbenzoate 0.82 0.11 0 .2 5 0 .2 7
TableXlll. Comparativechemical composition (%) of germacreneD 17.07 20.11 21.71 21.65
ylang ylang oil produced trom s-farnesene* 8.17 10.69 15.73 23.75
flowers harvested at different flowering times y-cadinene 0.64 0"78 1 .1 3 1 .2 5
6-cadinene 1.14 1.68 3 .1 2 3 .6 7
Compound yellow- isoeugenylacetate* o.12
yellow green green green T-amorphol 0.82 1.12 2 .0 0 1 .9 3
flowers flowers flowers buds
(Z,Z)- a-tarnesylacetate 1.31 1.60 2 .O2 1 .5 6
p-cresylmethylether 3. 40 1. 70
linalool benzylbenzoate 4.83 5.83 6.33 5.43
methylbenzoate 1. 19 0. 22 0.0 1 (E,E)-a{arnesylacetate 1.68 1.89 2 .7 0 3 .4 6
benzylacetate 0.05 benzylsalicylate 2.37 2.63 3 .0 5 2 .8 1
methylchavicol 0.05 0.01 * correctisomernot given
geraniol 0.52 2. 45 1. 20 0.2 1
c{-copaene 0.04 0.06 0.04
geranylacetate 2. 58 7.28 4.69 2.37
B-elemene 0.70 0.23 0.22 0.32
p-caryophyllene 31. 33 26.46 37.06 47.95 ca. 23Vo), and Grade III (fourth fraction, ca. 477o). The
cr-humulene 8. 35 6. 64 9. 28 11 . 6 8
'1-muurolene 13. 28 20-94 19.34
analysespresented in this report can be fbund in Table XIV
13.96
ciJarnesene* 9. 21 8. 09 10. 86 9.8 6 One year later, Stashenkoet al. (1993) analyzedoils pro-
lcadinene 0.40 0.34 0.23 0.26 duced from freshly hawested mature yellow ylang ylang
B-cadinene 1. 90 2.26 2.05 2.70 flowers, petals and ovaries of Colombian origin that were
6-cadinene 0.04 steam distilled for either I or 2 h. Usinq a combination of
6-cadinol 0.68 0.90 0.84 0.77
farnesol*
modern analyical techniquessuch as GC (KovatsIndices on
o.z5 4.52 3.99 2.34
benzylbenzoate I J.JJ 9.26 5.07 3.56 a DB-1 column), GC/MS, IR, ]H- and l3C-NMR they were
farnesylacetate* 2. 48 0. 79 0. 58 0.3 6 able to identifv more than 50 constituents in the oils. A
benzylsalicylate 0. 77 0. 44 0. 22 0.1 0 summary of these results can be seen in Table XV
dibutylphthalatei 1. 77 0.65 0.26 0.34
C.Yernin,Ddtectionet dtaluationdel'anthranilatedemethqlet deses
'correct isomernot given cldriuds naturelsetde.sqntlrcse
methylestlansdiffdrentdchantilltnts
artilact par CCM et CLC. La Franceet sesPa#urns, 9, 429-448(1966).
\7
M.S.F. Ross, Application of high-performonce
Iiquid cLrrorntography to the anahl sisof aolatile
oils. J. Chromatog., 160, f99-204 (1978). Table XV. Comparativechemical composition
K. Takahashi,S. Muraki and T. Yoshida,Sqnthesis of Colombianylang ylang oil
antl distributittn ,'f , -rplnlsulphide.- a nouel
utlfur- containin g sesquiterpene. Agric. Biol. Compound 1 2
Chem.,45, 129-131(r981).
3-hexenol* 0.05
J-Q C", Iunnan - The kingdom of essentialoil 2-hexenol* 0.11 t 0.41 0.04
plants. In: Flaaors and Fragrances: A World
2-methyl-3-buten-2-ol 0.35 0.20 0.03 t 0.07 0.03
Perspectioe.Edits., B. M. Lawrence, B. D.
Mookherjee and B. J. Willis, pp 23I-241,
3-methyl-2-butenol 0.07 t 0.08 0.07 I-
1B
Progress in Essential Oils
Reprinted
fromPerfumer
& Flavorist,
May/June
1995,Vol.20,No.3,P.67
19
produced from plants harvested in full flolver, was analyzedby
both GC and GC/MS. The comoosition of both oils was as Table ll. Comparativechemical composition
of thyme oils produced from various locations
follows:
in eastern Liguria
o{h ujene (0.87-2.10'/.) terpinolene (0.18-0.19%)
cr-pinene (0.49-1.34%) linalool(2"42-2.82k) Monte Punta Monte Gapo
camphene(0.18-0.46%) a-thujone(0.00-0.51 %) Compound RoccheitaCorvo Marlo Acqua Zezziggiola
sabinene(t) B-thujone (0.00-0. 15%)
(0.1 7-0 .41 % ) camphor(t-0.30%) o-prnene 0.92 1. 2 1 1. 15 1.64 1.3 1
B -pin en e
1-octen-3-ol(0.41-0.67%) borneol(0.44-0.45%) campnene 1. 11 2.16 1. 1 4 1.48 2 .3 1
myrcene(1.40-2.14'/") terpinen-4-ol (0.98-1"10'l") B-pinene 0.22 0.27 0.22 0.34 0.36
o-phellandrene (0.15-0.19%) p-cymen-B-ol(t) myrcene 1.71 1.47 1.62 2 - 29 1 .4 7
6-3-carene(0.07-0.13%) crterpineol(0.17-0.26%) limonene 0.33 0.48 0.86 0.37 0.37
methylthymol (1.43-1.52'/.) B-gurjunene (trace-0.04%) 1.8-cineole 0.23 1.13 0.62 0.84 2.54
thymoquinone (t) aromadendrene (t)
bornylacetate(0.04-0.07%) o-humulene(0.13-0.23%) yterpinene 11.O7 11.00 13.10 1 7. 1 7 1 0 .5 3
thymol(16.55-38.24'/.) (Z)-B{arnesene (t-0.04%) p-cymene 17.01 22.02 17.50 24.68 26.31
carvacrol(0.61-1.72'/") o,-muurolene(0.04-0.07'/") camphor 0 . 13 0.20 0.12 t 0.34
cuminylalcohol(t-0.08%) lorene(t-0.10%)
viridif linalool 0.44 0.30 0.65 0.75 0.78
c{-copaene(t) y-muurolene (t-0.08%) bornylacetate 2.34 1.93 0.81 0.41 1.19
B-bourbonene (t) y-cadinene (0.06-0. 15%)
B-caryophyllene0.38 0.19 0.34 1. 2 0 0 .16
B-caryophyl lene (2.38-4.28%) 8-cadinene (0.11-0.25%)
s-terpinene(1.67-2.34%) caryophylleneoxide cr{erpineol 1.26 0.23 0.16 t 0.32
p-cymene(18.60-25.34%) (0-29-0.45%) 2.59 2.44 5.02
borneol 1.35 4.55
lim on en e(0.1 7-0 .30% ) 6-cadinol(t-0.09%) geraniol 0.39 0.28 0.39 ti
1.8-cineole (1.96-2.26"/") cr-cadinol(t-0.05%)
thymol 31.39 11.33 36.66 17.31 1 0 .9 5
7te rpinene (12.06-12.27'/")
carvacrol 12.36 27.95 5.79 18.88 23.29
i = t r a ce (<0 .0 1 %)
t = trace(<0.01%)
It should be noted that these oils could not be used
conrmerciallv because of the lorv thyrnol content and the
richness of y-terpinene and p-cymene. 6-3-carene(t) cxterpinylacetate(0.25'/.)
Thirt same year, Salgueiro et al. (1993) analyzed an oil of Z myrcene(0.52%) oterpineol (0.27%)
: 111lsssp.:ygis of Portuguese origin using GC. The oil compo- (E)-B-ocimene (O.92"/") geranylacetate(0.35%)
rerrts. u-hich were mainly identified by retention times, rvere limonene(t) geraniol(0.18%)
(t)
1,8-cineole allo-aromadendrene (t)
l,-.rtinclto be:
y-terpinene
(0.93%) p-cymen-8-ol (0.68%)
cr-thujene (0.8%) linalool(3.8%) p-cymene(10.34%) thymol(74.00%)
u-cinere (0.7oo) bornylacetate(t) frans-sabinene hydrate(0.12o/o) carvacrol$.90'/4
carphene (0.6%) B-caryophyllene (1.5%) camphor(0.24eo)
:-c'nene(0.1%) terpinen-4-ol (0.9%) t=trace (<0.01%)
sacinene(t) cr-humulene (t)
-r''cene (1.3%) g-terpineol (0.1%) Furthermore, the authorsfound that this thymol chemofpe
r:r-rerpinene (1.07o) borneol(1.0%) ofT. zygis possessedanti-hepatotoxicactivity and free radical
-onene (0.4%) germacrene D (t)
scavengeractivity.
' 3-:ire ole(O.2o o) (t)
B- bis abolene
..-:erpinene (1s.0%) geranylacetate(0.2%) Thy mus oul gads, that was harvested in the wild in Italy was
r-.t,nene (19.9%) geraniol(0.3%) water distilled (Perrucciet al. 1994)to produce an oil thatwas
::rc rclene (t) thymol(0.2%) analyzedby capillary GC using retention indices asthe method
3-:c:anol(0.1%) carvacrol(42.0%) of componentidentification.The compounclsidentified in the
'-:c:en-3-ol(0.2%) caryophyllene oxide(0.6%)
oil were:
: ' ais-sa bin en eh yd r at e( 0. 2% ) ( 0. 1% )
v ir idif lor ol
:a- :-cr (0.5 0o ) (1.15%)
cr-pinene linalool(t)
<i.l ".) camphene(2.2170) bornylacetate(t)
B-pinene(t) B-caryophyllen e (1.46%)
Tlrrs is an erample of the carvacrolchemotype of T.zygis myrcene(1.35%) o-terpineol(t)
ssf-,::i:ii and not the thymol chemotlpe which is the raw limonene(t) borneol(4.60%)
1,8-cineole(2.56'/") geraniol(t)
n^:treri:Jused to produce the commercial red thyme oil.
y-terpinene(9.15ol.) thymol(7.30%)
d'o iri 1993,Jimenez et al. {bund that an oil of T. zygis oI p-cymene(31.19%) carvacrol (28.34%)
Spanishoriqin contained the fbllowing constituents: camphor(t)
t=trace(0.01%)
o,-tf,jjene(t) linalool( 0. 16% )
a-pirene(0.40%) Iinalylacetate(0.22%)
camp .en e(l) (t) Basedon the abovecomposition,it is obviousthat this oil
B-caryophyllene
sabinene(t) terpinen-4-ol(2.32'/.) is not related to those found in commerce.
(0.1 0% )
B - pin en e borneol(t)
20
Using :i combination of GC and GCIMS, the oil of I In 1990, Sugimura et al. used both GC and GC/MS to
ttigari,s that has become naturalized in Nerv Zealand was compare tlie chemical composition of three cultivars of
reported (McGimpseyet al. 1994)to contain: patchouli. One cultivarwasobtained from Tairvan(cultivar I),
s-thu jen e(0 .1-1 .1%) the secondone ii-omthe Philippines (cultivar II) and the third
borneol(1.2-4.7%)
c-p ine ne(0 .1-1.1 % ) terpinen-4-ol (0.4-0.7%) one (cultivar III) from Japan.The authors determined that
camphene(0.2-1.6%) cr-terpineol (0.3-0.7 %) the biomassyield per plant, the oil vield per plant and tlie
B-pinene(0.5-1.2o/") methylcarvacrol(O.a'a.0%) percent oil yield were as follows:
myrcene(0.8-2.1%) methylthymol(0.9-2.8%)
p-cymene(19.8-55.9%) thymol(9.5-37.4%) Biomassyield Oityietd Oil
lrmonene + 1,8-cineole ( 1. 5- 11. 0%)
c ar v ac r ol perplant perplant yield
(2.2-4.2o/o) (1.5-3.8%)
Cultivar (S) (S) (t")
B-caryophyllene
T-terpinene (1.9-19.1%) germacreneD (0.3-12%) | 26.8 0.43 1 .6 0
linalool(2.7-5.5%) caryophyliene oxide(0.5-1.9%) ll 27.2 0.27 0.99
camphor(0.4-1.3%)
ilt 140.6 t.oo '1.1 8
it is worth noting that the authors are pursuing the potential Horvever, the trichome density (number of essential oil
of establishing this or othe r Thymus utlgarls accessions as the glands per leaf) was greatest for crrltir-ar I ancl lorvest frrr
brrsisfor commercial production of thyme oil in the semi-arid cultivar III. The chemical composition obtained from oils
region ol'central Otago (Nerv Zealand). produced from the three cultivats be seen in Table III.
"an
H. J. Bestmann,f . Erler and O. Vostrorvlg',Ertraktion utn Thynian In 1992, Hasegar,vaet al. characterized germacrene B as a
rnit fli.issigernC02 in Labo,nnasstrLb.Zeit. Lebersmitt. Unters constituent of'patchouli oil. Usirrg oil obtained from the
Forsch.,180" 491-493(19S5). above-noted cultivar II, the iruthors were able to demclnstrate
P. Kreis, D. juchelka, C. Motz and A. MosandI,Chirale inhaltsstoffe the Cope rearrangernent of germacrene B to y-elemene and
iitherischerOla. Deutsch. Apoth. Ztg., l3l, l9B4-19E7(1991): shor'vhou' to pre'r'ent it during patchouli oil analysis.
R. Plccagliaarxl \{. Nlarotti, Conrytositionof the e,ssential
oil of an Analysis of the basic {raction of'patchouli oil using prepara-
Italiur Thyrrntsxulgaris L. ecotype.Flav. Fragr. 1., 6,211-214 tive GC, ltt-NVn
(19e1). and MS, Maurer and Hausei (1992)
characterized the presence of four sullstituted pvridines in
-{. Krrrolr'ska,D. Kalernba, J. Gora and T. Majda, Aralr1sis of essential the oil. The con'rpounds identified were:
oils, a,spectsof their inJhtcnceto insects.Paft IV.'Esserrtial oil of
garrlenthqme(Thqnu,satlgard,sL.). Pestycvdy,(2), 25-29 (1991). (Z)-3-(l-butenyl)
pyridine (Z)-3-(t-butenyt)-4-propytpyridine
S. \Itrccioni, G. Flamirii, P. L. Cioni and P. E. Tomei, Le Tipologie (E)-3-(l-butenyl)
pyridine (E)-3-(l-butenyt)-4-propytpyridine
fitochinLicLrc in Alcunepopolazionidi Thytnts u.tlgnrisL. p resenti
uLl promontorio del Caprione (Liguria Orientale). Rir.ista Ital. Although the authors did not present qualitative data, it is
E PPOS.';'. I3 -18 119927. saf'eto say that the four cornpounds rvere present only in ppm
R. Piccaglia and NI. Nlarotti, Characterization of su;eral oronuttic levels.
plantsgrcrcninnofthern Itolll.Flav. Flagr. J..8. 115-122(1993). Also in 1992, Mookherjee et al. reported on the character-
L. R. Salgueiro,A. Proengada Cunha and J. Paiva,Clrcmotoxonornic ization of a number of new constituents in patchouli oil. The
clmracterization of a Thynus hrlbridfrom Poflugal. Flav. Fragr. r r e w l y i d e n t i f i e d r . o m p o n e n t s r , re r e :
J. , 8, 32 5-3 30( 19 93 ) . guaiolpyridine
T.Jirnenez,M. C. Navarro,NL P.lvlontilltr,A.Maftin, andA. Martlnez, dehydroguaiolpyridine
lhynus ;qgis oil: its fficts ot'tCCll - ind,ucedhepatotoricityand 1,2-dimethylcyclohex-1
-en-3-one
-free-radir:ttlscal)engeractiuittl. J. Essent. Oil Res., 5, 153-155 (syn.2,3-dimethylcyclohex-2-en-1
-one)
( 1993).
T 1,2-dimethylcyclohex-2-en-4-one
S. Perrucci, F. Nlancianti,P. L. Cioni, G. Flamini, I. Morclli and G. (syn.3,4-dimethylcyclohex-2-en-
1-one)
Macc}rioni, ln, xitro antifintgal actixity of cssentktl oil,s against 1,5-dimethylcyclohex-1
-en-3-one
so_nei,solatesof Xtlicrospo,nnrL conis and MicrosporurL glJpseunt. (syn.3,6-dimethylcyclohex-2-en-1
-one)
Plant NIed.,60, 184-r87(1994). rsophorone
J. A. McGimpsel', VL H. Douglas,J. W. r'an Klink, D. A. Beauregard (syn.3,5,5-trimethylcyclohex-2-en-1
-one)
and N. B. Perw, Seusonal uoriatiort in essential oil tliekl and. 1,5-dimethylcyclohexa-3,6-dione
compo sitionfrom naturalized Tlty ntus aulgad.sL. in N er Zealantl.. (syn.2,6-dimethylcyclohexa-1,4-dione)
Flav. Fragr.J.,9,347-352(1994). 1,5,5-trimethylcyclohexa-3,6-dione
(syn.2,6,6-trimethylcyclohex-2-en-1,4-dione)
Pa tchouliO il 1,2,5,5-tetramethylcyclohexa-3,6-dione
(syn.2,3,4,4-tetramethylcyclohex-2-en-1,4-dione)
Using a cornbinationof GC/MS, GC-FTIR and a GC-sniffing
B-patchoulone
procedure, Nikiforov ei al. (1988) determined that the con- s-patchoulone
stituentsof patchoulioil thatpossess
the mostintensepatchouli- 5-oxopatchoulol
lrKeilrotta were: s-guarenone
,tr patchoulol o-bulnesene
0,-cedrenal
27
patchoulialcohol cr-guarenone
norpatchoulenol -en-3-
1,2-dimethylcyclohex-1 Table lll. Comparativechemical composition (%)
of three cultivars ol Pogostemon cablin
nortetrapatchoulol isophorone
p-patchoulenone l,5,5trimethylcyclohexa-3,6- Gompound I illillv
drone
(-cedrenal 6-elemene t.bv 1.34 1 .O2 1 .8 8
0-copaene - 0 "5 4 3 .1 7
TLresane vear,Guan et al. (1992)studiedthe composition cr-guaiene+p-caryophyllene 17.37 13.99 5 .0 6 1 6 .5 8
o,-patchoulene+ 6-guaiene" 12.32 8.93 6.55 14.02
iCLrirese patchouli oil using GC/MS. They found that the
R-natchorrlcnc 0.91 0.63 0 .5 1 1 .0 8
:l cantailed: cx-humulene 0.57 0.62 0.36 0.74
Fnethyl-2-pentanone(0.01%) verbenone(0.02%) longifoleneb 2.72 1.72 18.36 2.27
rexanal(0.01%) myrtenol(0.02%) guaiene* 18.80 13.21 2.BB 14.44
i..nethyl-2-hexanone(0.01%) perilla ketone(0.02'/.) norpatchoulenol 1.08 0.11 0 .0 8 0 .5 8
o-plnene (0.09%) thujone-(t) patchoulialcohol 29.07 22.83 19.02 29.03
camphene(t) 8-elemene(0.04o/")
1-hepten-3-ol (0.01%) (6.91%) Legend: | = Cultivarfrom Taiwan
B-patchoulene ll = Cultivarfrom The Philiooines
lpinene (0.26%) B-caryophyllene (3.1B%)
ll = Cultivarfrom Japan
rimonene(0.02%) cx-guaiene (8.82%) lV = Commercialsamoleof Patchoulioil
rinaiooloxide. (t) seychellene (9.58%) a also knownas B-bulnesene
;inalool(0.01%) cr-patchoulene (8.48'/") b probablyseycfrellene not longifolene
* correctisomernot identified
isophorone(0.03%) B-maaliene (0.66%)
fransverbenol(0.03%) 6-9uaiene(8.65%)
4-methyl-1 Juranyl-1 -pentene y-selinene (0.11%)
(0.0 1% ) ar-curcumene (0.21'/.)
sopinocamphone (0.01%) patchoulialcohol(31.86%)
terpinen-4-ol(0.01%) pogostone(3.83%)
dihydrocarvone.(0.01%) aristolone(0.85%)
' .oqect isomer not identified
:=lne (<0.01olo)
22