Progress in Essential Oils

& Flavorist,
fromPerfumer
Reprinted 1997,Yol.22,No.2,P.59
March/April

TeaTreeOil
Table L Comparativechemical composition (%)
In 1990.Kawakamiet al. used a combination of GC and CC/ of the headspace and oil of tea tree
MS to exarninethe headspaceand volatile oil produced by grown in California
simultaneousdistillation and ertraction of eight different
clonesoftea tree. The resultsofthis study are found in Table Compound Headspacea oil
I. As can be seenfrorn the results.the range of con'rposition d-prnene 0.98-7.28 | .J3 - J. / |

{bund is quite huge. Consequently,it is obviousthat seedling o-thujene 0.02-13.38 0.03-4.24

reproduction oI Meloleuca olternfolia does not yield a inene 0.70-3.63 0.53 - 1. 30
saornene 1. 6 5 - 4 9 . 1 4 0.23- 10. 93
very reproducible tight oil composition.
myrcene 2.20-6.69 1.2 6- 3, 57
The following year, Lassak(i991) noted that there were cx,-terpinene 0.95-19.82 0.63- 10. 37
two chemical fbrms of tea tree oil (ex. M. alternifolia); one ltmonene 1.87-10.55 0.6 1- 6. 97
rich in teminen-4-ol with a low level of 1,S-cineoieand the B-phellandrene 0.50-1.91 0.29-0.93
other richln l,S-cineole with a riroderatelevel of terpinen- 1,8-cineole 2.57-52-37 0.54-56.1 0
y-terpinene 0.99-24.63 0.94- 19. 36
4-ol. The sameauthor alsonoted thatterpinen-4- ol and 1,8-
p-cymene <0 . 0 1 - 9 . 9 7 0.05-3.82
cineole have been found in three other MelcLlettca species: 1.78-23.98
terpinolene 1.77-33.12
(35-52%)
M. dissitifotia: terpinen-4-ol and1,8-cineole(1'5-2.0"/") cycronexanone 0-0.17
(3.5-8.0%)
(30-37"/")and 1,8-cineole
M. tinariifotia: lerpinen-4-ol (Z)-3-hexenylacetate 0-0.29
M. uncinata:lerpinen-4-ol (ca.4.O%) and1,8-cineole (ca 0.5%) trans-sabinene hydrate 0-0.48 o-o.zs
B-cubebene 0-0.12 0- 0.41
As part of a distillation study, Johns et al. (1992) deter- cx,-gurlunene 0- 0. 16
mined that an oil produced from tea tree tr'vigsand leaves linalool 0-0.14 0-0.34
cls-sabinenehydrate 0 - 1. 1 4 0-o.74
han estedat one ofthe tea tree estatespossessedthe follow-
trans-p-menth-2-en-1-ol 0-0.08 0- 1. 41
ing composition: 0-0.12 0-0.65
B-caryophyllene
(2.5%)
cx-pinene
'1
,B-cineole(2.9%) terpinen-4-ol 0 . 16 - 3 .15 1.0 7- 42. 85
yterpinene (20.4%) allo-aromad endrene 0-0.10 < 0.01- 0. 23
B-pinene(1.6%) <0.01-0.24
myrcene(0.3%) terpinolene (9.27%) B-cadinenet
terpinen-4-ol (12.10%) cis-p-menth-2-en-1-ol < 0. 01- 0. 90
a-terpinene(9.4%)
p-cymene(2.1%) cr-tepineol(12.26%) viridiflorene < 0. 01- 0. 43
limonene(0.9%) trans-piperitol 0-0.39
oterpineol o . z o -r. ro 2.65-9.59
Although the authorsnoted that there were indeed other T-elemener 0-0.20 < 0. 01- 0. 50
oil components, particularly sesquiterpenes,these were 6-cadinene 0-0.21 0.21- 0. 93
cls-piperitol 0.01- 0. 45
purposely not determined.
- cadina-1 ,4-diene 0 - 0.41
ftr" following yeaq Leach et al. (1993) used a chiral calamenene* 0- <0. 01
column to perform an enantiomeric analysisof Australian p-cymen-B-ol 0 - 0. 10
tea tree oil. The compounds identified r.vere: 1-epi-cubenol 0. 21- O . 54
p-eudesmol 0. 10- 0. 32
cr-thujenet(o.44%) 1,8-cineole (3.O4%) 0-0.21
T-cadinol
(-)-cr-pinene(0.18%) a-p-dimethylstyrene (0.17e.)
6-cadinolb 0-o.47
(+)-cr-pinene(1.68%) (t)
(-)-linalool
myrcene(0.46%) (+)-linalool(t) . correctisomernot identified
..
(-)-cx-phellandrene(t) sabinenehydrate. (t) f probablyincorreclidentification
(+)-cr-phellandrene(t) (+)-terpinen-4-ol(24.73%) " rangeof data lrom eightindividualclones
o also knownas cr-muurolol
crterpinene(9.90%) (-)-terpinen-4-ol (13.13%)
(-)-limonene(t) (-)-cx{erpt?teol (0.69%)
p-cymene(4.960/") (+)-aterpineol(2.03%) B-caryophyl lene (0.aa%) cr-muurolene(0.26"/")
(+)-limonene (0.51%) cr-copaene (0.17%) o-bulnesene (0.19%) methyleugenol(trace)
1,4-cineole (trace) o-cubgbene(0.09%) aromadendrene (1.61%) cr-amorphene (0.29%)
(-)-B-phelland rene(0.22%) p-cymdh-B-ol(t) y-gurjunene (0.15%) bicyclogermacrene (0.13%)
(+)-B-phellandrene (0.36%) cr-gurjunene (0.45%) allo-aromadendrene (0.69%) viridiflorene(1.75o/")
y{erpinene(21.15o/o) B-gurjunene (t) 1-epi-bicyclosesquiphellandrene6-cadinene (1.86%)
terpinolene (3.18%) B-maaliene (t) ( 0 . s 1 %) calamenene* (0.27%)

t14
 ca din a-1 ,4-d ien e( 0. 30% ) globulol( 0. 80% )
palustrol(0.06%) cubenol(052%) Table ll. Comparativechemical composition (%)
epi-globulol (0.18%) (0.58%)
viridiflorol of the main components of fresh and
spathulenol (0.15%) oxidized tea trea oil
* correctisomernot identified
." chiralitynol determined Component Freshoil Oxidizedoil
t = t r a c e( < 0 . 0 1 % )
cr-pinene 3.5 4.2
In 1994, Williams and Lusunzi examined the oils pro- B-pinene 0.7 0.8
duced from 30 treesof M . dissitiflora.They found that the oil o-terpinene 10.3 2.1
1,8-cineole 5.0 5.0
compositionsvaried as follows:
y-terpinene 20.5 B.B
(1.3 -65 . 4% )
1,8-cine ole (5.2-55.3%)
terpinen-4-ol p-cymene 4.3 21.5
p-cymene(0.8-18.5%)
terpinolene 3.6 1.8
The authors showedthat the oils thatu,'ererich in teminen- terpinen-4-ol 37.4 34.1
4-ol exhibited antimicrobial characteristicssimiiar to tea cx,-terpineol 3.2 2.9
tree oil ex. M. ahernifolia.
The following year, Ravid et al. (1995) found that the
enantiomeric distribution of o,-terpineol (LgEa) in tea tree linalool and o-terpineol were activeagainstall test organisms
oil rvas( +)- (4R)-u-terpineol (7SVo) : (-) - ( 43)-u-terpineol (2550). except P. aetuginosa. It 'uvasunfbrtunate that the authors
Williams and Home (1995)comparedthe compositionof did not screen pure enantiomers of linalool, terpinen-4-ol
a sample of freshly distilled tea tree oil with that of an and o-terpineol, becausethe antimicrobial activity of the
oxidized oil. The oxidized oil r,r'asprepared from freshly pure enantiomerscould be quite diff'erent.
dlstllled oil placed in a large container sothata large surface Using radiotracerstudies,Cornwell et al. (1995)reported
areahad direct contactwith the air.A summaryof the results that the terpinen-4-ol, o-terpinene, y-ter?inene, p-cymene
of the analysesis shownin Table II. As can be seen,the main and terpinolene found in tea tree oils as main components
changesare the increasein p-cymene causedby the partial are primarily formed from cis-sabinenehydrate and to a
oxidation of cr-terpineneand y-terpinene. lesserextent from trans-sabinenehydrate.They determined
Also in 1995. Bishop determined that a tea tree oil con- that the enantiomeric distribution of teminen-4-ol found in
tained the following maior components: both young and old tea tree leaveswas sir]rilarto that formecl
a-thujene(0.8%) 1,8-cineole(3.4%) fiom acid hydrolysisof sabinenehydrate.Cornwell et al. also
o-pinene(2.3%) y-terpinene(19.4%) determined that 607oof the teroinen-4-ol ibund in tea tree
B-pinene(0.7%) p-cymene(2.0%) oi l r,ras fbrmed as a arti tacfduri ng di sti l l ati on.
myrcene(0.8%) terpinen-4-ol(37.4o/o)
l (9.0olo)
cr-terpinene (2.5%)
In 1996, Southwell et al. reported that there was no
i o-terpineol
evidenceto support an industry misconceptionthat tea tree
I limonene(0.9%)
oils which possessultra lorv levels of l,S-cineole were
Bishop was alsoable to show that the number of tobacco superiorto oils with higher levelsof I,8-cineole.The authors
mosaicvirus lesionson a leaf of Nl cotianaghLtinosacould be showed that oils with higher levels of l,8-cineole (up to
reduced substantiallyby using a pre-inoculation spray of 15%) possessedantimicrobial characteristicscon'rparableto
100-500ppm tea tree oil. This is one ofthe first reports ofan oils with Iower levels of 1,8-cineole.In addition, it has been
oil possessingantiviral activity,albeit with the largestknou'n confirmed that concentrationsof 1,S-cineolein tea tree oil
plant virus, namely the tobacco mosaicvirus. did not cause tea tree oil to become a skin irritant or an
This same year, Carson and Riley (1995) examined the antagonistto its biological activity.
antimicrobial activityof eight conlponentsof teatree oil (1,8 Also in 1996, Verghese et al. reported the results of
-cineole, linalool, terpinen-4-ol, u-terpinene, o(-ter?ineol, a combined GC and GC/MS analvsisof Indian tea tree oil.
y-terpinene,p-cymene and terpinolene) against12 different The componentsi denfi fi edi n f heoi l r,rere:
microorganisms.This study was done bec:ruseof the exten-
o-pinene(3.4%) B-caryophyllene (0.1%)
siveuseof tea tree oil for its antirnicrobialactivityand the vast
B-pinene ( 1 . 0 %) terpinen-4-ol (36.4%)
number of studies that have appeared in the literature s a b i n e n e( 1 . 3 %) allo-aromadendrene (<0.19"/
evaluating and extolling this activity. Using disc diffusion myrcene(1.2%) viridiflorene (0.2%)
method of screeningfor antimicrobial activity,it was found oterpinene(11.9%) aterpineol(2.6%)
that terpinen-4-ol was active againstall 12 microorganisrns I i m o n e n e( 1 . 4 %) y-cadinene(0.9%)
1,8-cineole (4.5%) c a l a m e n e n e(-0 . 1 %)
(Bacilhts,subtilis, B acteriodes frag{is, Canclicla albicans,
y-terpinene(23.0"/.) p-cymen-8-ol (<0.1%)
Clostridium p erfrin gens,Ent erococcusfo ecalis, Escl'terichia p-cymene(5.6%) ledol(<0.1%)
coli, Lactob ocilfu ,sacidophilus, M oraEellacatarrhalis, My co- terpinolene (4.2%) rosifoliol (<0.1%)
bacteritrm smegmatis, Pseudomonas aeruginosa, Serratia o-gurjunene (0.1%)
lnarce,scensarJ Staphylococcltsaureus), while p-cymene * correctisomernot identified
demonstrated no activity at all. Further, it was fbund that
 The oil was produced from M. alternfolia grown erperi- o-phellandrene (1.3%) ct-copaene(0.2%)
6-3-carene (16.0%) B-caryophyllene (10.0%)
mentally in Kerala from Australian seed. The authors indi-
oterpinene(0.1%) cx-humulene (0.3%)
cated that, since the produced oil possessed a composition p-cymene(0.3%) o-guaiene(t)
similar to Australian oil, production of this oil commercialiy (Z)-B-ocimene (0.1%) o-cubebene(t)
in India might prove to he of high economic potential, 1 , 8 - c i n e o l(e0 . 1 %) ar-curcumene(t)
Finally, it is worth noting that a few years ago, tea tree oil l i m o n e n e( 1 9 . 0 %) 6-guaiene(t)
(E)-B-ocimene (0.1%) o-selinene(0.6%)
production was no more than l0 tons (Lawrence, 1985),
^yterpinene(0.2%) (E)-B-farnesene (t)
wherein currently it exceeds 300 tons. cis-sabinene hydrate(0.7'6) (0.6%)
B-bisabolene
terpinolene (0.2%) 6-cadinene(t)
B. M. Lawren ce,A reoieu of the wolld producti,on of essentioloils linalool(0.8%) (t)
B-selinene
(1984).Perfum.Flavor.,rO(5), r-16 (1985). trans-sabinenehydrate elemol(0.9%)
M. Kawakami, R. M. Sachsand T. Shibamoto,Volatite constifircnts (0.4o/o) nerolidol.(2.5%)
of essential oitsobtainedfrom neuly deaelopedtea tre e (.Melaleuca c a m p h o r( 0 . 1 %) caryophyllene oxide(0.7%)
altemifolla) ck-rnes. J. Agric. Food Chem.,38, f 657-1661(1990). terpinen-4-ol (0.8%) h u m u l e n eo x i d e -( 0 . 1% )
tr,V. Lassak,Bacte4al ctilsof Melaleuca. Achemical re-inaestigatiort v-terpineol(0.2%) T-muurolol(0.5%)
of the essential ctilM. altemifulia Cheel(MtJftaceae). In Trnisieme nerol(trace) B-eudesmol (0.6%)
6-elemene(t) guaiol(0.2%)
Symposium sur les substancesnrLturellescl'interet biologique d.e
laregionPacifiqueAsie.Edits.,C. Debitus,P. Amade,D. Laurent eugenol(t) (Z,E)larnesol(t)
B-elemene (t)
and J.P. Cosson,pp. 177-181, Noumeu, Nouvelle Caledonie
(19 91 ).
M. J. Johns,J. tr. fohns and V. Rudolf , Steamdistillatior'r of tea tree t = tr ac e i < 0.1% )
(Melaleucoahernfolta) oll. J. Sci. Food Agric. 58, 49-53 (1892).
Two years later, some of the same authors (Pino et al.
D. N. Leach, S. G. Wyllie, J. G, Hal1and I. Kyratzis,Enantiomeric 1992) showedhow to deterpenify a sample of black pepper
composition of the principal cornporrcntsof the oil of Melaleuca
oil using a 1:2 oil to alcohol (60 % aqueous)ratio. The results
altemifolia. J Agric. Food Sci.,41, 1627-f632 (1993).
of this deterpenationprocessare shown in Table III. It is of
tr. R. Williams and I. Lusunzi, Essentialoil.from Melaleucadissitifulia:
a potential source of high quallty tea tree oll. Industrial Crops
interest to note that in addition to removing the monoter-
Products, 2, 2Il-2L7 (1994). pene hydrocarbons,extraction with 607o aqueous ethanol
U. Ravid,E. Putievslyandl. Katzir,Deterntination ofthe enantiomeric also removed almost all of the sesquiterpenehydrocarbons.
composition of a-terpineol in essential oils. Flav. Fragr. J., 10, This sameyear,Konig et al. (1992)usedchiral GC analysis
281.284(1995). using either a 6-methyl-2,3 -di-O-pentyl-B-cyclodextrinor
L. R. Williams and V. N. Home, Factors detenniningtLrc quality a 6-methyl-2,3-di-O-pentyl-y-cyclodextrin capillary GC
of tea tree oil in formulations for clinical zse. Cosmet. Aerosol. column to examinethe monotemene hvdrocarbonsof black
Toilet., Australia,9(2), 14-24 (1995).
pepper oil. They {bunclthat the nonoierpene hydrocarbon
C. D. Bishop, Antidral actiuitA of the essential oil of Melaleuco iiaction of black pepper oil contained the follorving:
alternifolia (Maid,en et Betche) Cheel (tea tree) against tobacco
mosaicr:irus. f . Essent.Oil Res.,7,641-641 (1595).
C. F. Carson and T. V. Riley, Antimicrobial octiuitrl of the mtLjor
contponentsof the es,sentialoil of Melaleuca alternfolia. J. Appl. Table lll. Chemicalcomposition(%) of black pepper
Bacteriol.,78, 264-269 (1995). and the deterpenifiedversion
C. P. Cornwell, D. N. Leach and S. C. Wyllie, lncorporation of
On1gen-1B into teqtinen-L-ol from the H rrsO steam distillates of Compound Originaloil oil
Deterpenified
Nlelaleucaalte'rnifolio(,teatree). J. Essent.Oil Res.,7, 613-620
(1ee5). athujene 1.4
0-prnene 6.7
I. A. Southrvell,J. Markham and C. Mann, Is cineolecletrimentalto campnene 0.1
teatree oil,pPerfum. Flavor., 21(5), 7-10 (1996). sabinene 22,0
j. Verghese,C. V. jack., C. V. Kunjunni Kartha, M. McCarron, A. J.
B-pinene 3.4
Mills and D. Whittaker, Indianteatree (,Melaleucaaltemfolio)
myrcene 5.2
Cheelessentictloil. FIav. Fragr f., 11,219-221 (1996).
p-cymene 0.1
limonene 19.6
Black Pepper Oil
(E)-B-ocimene 0.5
In 1979, Takahashiet al. characterizedthe presence of a y-tepinene 0.3
trace amount of mint sulphide in black pepper oil. Many linalool 0.4 8. 3
years later, Pino et al. (1990) used @/MS to analyze a terpinen-4-ol 0.41 +. J

sample of lab-distilled oil of black pepper produced fiom c{,-terpineol 0.1 2 .1

freshly ground pepper of Indian origin. The compounds B-caryophyllene 19.8 o.2
identiiied in the oil were: caryophylleneoxide o.4 I c r. c
nerolidol. 0.6 14.3
o-thujene(0.8%) sabinene(19.0%)
* correctisomernot identified
o-pinene(8.2%) o,-pinene(12.0%)
camph en e(0.1 % ) myrcene(1.2%)
 Table lV. Chemicalcomposition(%) Table V. Chemicalcomposition (o/o)
of green pepper and black pepper oil of various black pepper oils

Compound Green pepper oil Black pepper oil Oven

ct-prnene 8. 5 8. 8 Compound Control drieda Microwavedb
B-pinene 10.4 11. 0 ctthujene 2.1 2.7 2 .6
cr-phellandrene 14.9 1a A s-prnene 7.8 9.8 8 .9
myrcene o. l 6 .3 camphene 0.2 0.3 0 .1
limonene 1 1 .9 I l.o
sabinene 17.9 2 1. 4 1 9 .0
B-ocimene- 0 .4 0 .3 B-pinene 15.7 16.8 I o.o
p-cymene 0 .7 0 .5 6-3-carene 2.0 t.o 1 .4
terpinolene 0 .5 0 .2 ct-terpinene 9.9 10.2 9 .2
terpinen-4-ylacetate 0.4 0 .2 B-phellandrene 0.6 1.0 0 .7
cubebene* 0.9 10 limonene 24.0 24.5 22.3
B-caryophyllene 9.1 14.0 (E)-B-ocimene 0.5 0.3 T
cx-humulene 0.1 0 .1 y-terpinene 0.5 0.4 0. 3
no terpinolene 0.1 0.1 0. 1
elemene* 0 .7
B-selinene 0 .2 0 .1 frans-linalool
oxide (furanoid) u.o 0.4 0. 4
q,-selinene t.3 0 .7 linalool 0.3 0.2 0. 4
B-bisabolene 1 .9 1 .8 frans-p-menth-2-en-1-ol 0.1 I

0.4 citronellal 0.1 i

B-cadinenst 0 .6
elemol 0 .9 2 .7 terpinen-4-ol 0.6 0.5 0 .6
cedrenol 0 .3 0 .6 a-terpineol 0.2 0.1
cr-euoesmol 0 .1 0 .1 carvoneoxide* 0.1 I

B-eudesmol 0.1 0 .3 6-elemene 0.1 0.1 o.;

* correctisomernot identified
cr-cu0e0ene 0.1 0.1 0. 1
o-copaene 1.2 1. 7
t tentativeidentification
B-elemene I t 1
B-caryophyllene 5.3 4.1 7.2
(+)-crthujene(0.11o/o) (+)-6-3-carene
(0.98%) farnesene* 0.1 0.1 0. 1
(-)-cr-pinene
(6.45%) (-)-6-3-carene
(36.98%) o(,-amorpnene 1.0 t I
(+)-or-pinene
(2.20o/o) (0.14o/o)
o,-terpinene cx-humulene u.o 0.2 0. 4
(-)-camphene (0.20%) p-cymene (2.47"/") cr-guarene 0.1 I 0. 1
(+)-camphene(0.10%) (+)-p-phellandrene(0.20%) or B-cubebene 0.t 0.1 0. 1
B-selinene
(-)-B-pinene(14.77'/") (-)-limonene
(16.750/") 0.1 0.1
Y-muurotene U.J
(+)-B-pinene(0.40o/o) (+)-limonene
(10.38%) valencener t t t
myrcene (3.25%) yterpinene(0.21"/") o,-bisaboleneor B-bisabolene 1.2 1.2 2. 3
(+)-cr-phellandr
ene(4.28"k)
6-cadinene 0.4 0. B
In addition, the authors determined that the oil was elemol 0.3 I I

d e vo i d of ( - ) - o- t huj e n e , (+ )- o r (-)-s a b i n e n e , (-)-u- nerolidol* 3.0 1.0 2. 4

caryophyllenealcohol 0.1 0.1 0. 3
phellandrene and (-)-B-phellandrene.
Two yearslater,Konig et al. (1994)examinedthe enantio-
caryophylleneoxide I 0.1 t
guarol t t 0. 1
meric distribution of three sesquiterpenehydrocarbonsin P cubenol t 0. 1
rtigrum oil. They found the following: cadinol. 0.2 0.2 0. 5
(+)-3-cadinene
(80%): (-)-b-cadinene
(20%) B-eudesmol I 0.1
(+)-B-elemene
(1%): (-)-B-elemene
(99%) a-eudesmol t
(+)-o(-copaene
(<1%): (-)-a-copaene
(>99%) B-bisabolol 0.2 0.1
- correctisomernot identified;t tentativeidentification;
"oil producedfrom
In addition, the racemic mixture of 8-elemenewas found. berriesdriedfor 30 minutesat 150"C:b oil oroducedf rom berriesdriedfor
The authorspostulatedthat the characterizationof a racemic =
2 minutesat high microwaveheat;t trace (< 0.1%)
mi-rture was a clear indication that 8-elemene originated
tiom the non-chiral precursor germacreneC via a thermally an elemene isomer and B-cadinenemust be in error, asthey
induced Cope rearrangement. are known to elute in positionsthat differ from those shown.
The following year,McCarron et al. (1985)used a combi- More recently, Chacko et al. (1996) compared the com-
nation of GC and GC/MS to analyzet[,e composition of oils position ofoils produced from Indian black pepper berries
producedfrom crushedgreenpepper berries and comminuted dried either in a forced air oven or a microwave oven. The
black pepper berries of Sri Lankan origin. The compounds results of the GC and GC/MS analysesof the oils are
identified in the oils are shown in Table IV It is worth notins presented in Table V. The value of this study is that the
that the compounds listed in Table IV are in elution ordei authors have shown that when black pepper is dry roasted
tiom a non-polar column, and therefore the identification of the oil composition does not change.
K. Takahashi,S. Muraki, T. Yoshida,C. Kabuto, T. Ohnuma and T. phenol linalool
Kato, Minut e components of p ep Stem i nt o il. 2. Sqnthesis of o new p-nitrophenol cinnamylalcohol
sulplur containingcompotindMint sulphide.ond itsdi'stribution. o-benzylphenol oterpineol
Koen Yoshishu Koryo Terupen o1'obi Seiyu Kagakul in kansuru p-vinylphenol 2-phenethyl alcohol
Toronkai, 23rd 36-3E (1979). p-methoxyphenol 2-(p-methoxyphenyl) ethanol
eugenol 3-phenylpropyl alcohol
Chemicaland
J. Pino, C. Rodriguez-Feo,P. Borgesand A. Rosado, (Z)-isoeugenol terpinen-4-ol
sensory propefties of black pepPer oil. Nahrung, 6, 555-560
(E)-isoeugenol spathulenol
(leeo).
hydroquinone lilacalcohol.
Pino, P. Borges and R. Sanchez,Alcoholdeterpenatittnof .black benzylformate hexyleneglycol
"J.
pepper oil. Intl. J. Food Sci. Technol., 27 , 555-557(1992). cinnamylformate y-isogeraniol
W. A. Konig, A. Kriiger, D. Icheln and T. Runge, Enrtrftiomeric (Z)-3-hexenylacetate heptanal
comnositlon of tlrc ch,iral cttnstituents in essential oils. Paft 7,
k^ 6 - "t
u 9 i l zyr ^ ^u^vl+^
d o r+^
E (2E,62)-nonadienal
Monoterpene hqdrocarbons.J. High Resol. Chromatogr., 15, prenylacetate decanal
184-i89 (1992). 2-phenethylacetate undecanal
2-(p-methoxyphenyl) ethyl dodecanal
\V. A. Konig, A. Reick, I. Hardt, B. Gehrcke, K-H. Kubeczka and
acetate tridecanal
H. Muhle, Enantiomeric composition of the chiral constituent's
3-phenylpropylacetate (E)-cinnamaldehyde
of essential oils.Part 2. Sesquite:ene ltydrocarbon,s.J. High
(Z)-cinnamylacetate p-menth-1 -en-9-al
Resol.Chromatogr.,17, 315-320(f994).
(E)-cinnamylacetate B-cyclocitral
M. McCarron, A. Mills, D. Whittaker, T. Kurian and J. Verghese, a^ ^t i ^i.,1
l D yt a^ ^u^vr+^
d l+^
v Iilacaldehyde-(3 isomers)
Composition between green and. black pepper oils from Piper lilacacetate- 3,4-dimethoxybenzaldehYde
nigrunt L. berciesof Inclian and Sri Lankan ongln. Flar'. Fragr. d a r a n \r l r n a t2 l a vanillin
(1995).
J.,r0,47-50 benzyl3,3-dimethylacrylate ct-ionone*
N. Chacko,A. jayalekshrny,M. Gopalakrishnanand C. S. Natarajan, methylbenzoate B-ionone-
Roastingsiuiliesonblackpepper (Piper nignim L.). Flav. Fragr. hexyl benzoate campnor
I, 11, 305-310(i996). 2-phenethylbenzoate 2,6,6trimethyl 2-
3-phenylpropyl benzoate hydroxycyclohexanone
Narcissusand lts Extracts methylp-hydroxybenzoate 2-tridecanone
cinnamylbenzoate* 2-pentadecanone
In 1966, Vernin determined that narcissusabsolute con- benzylbenzoate 2-methylbutyric acid
tained a trace amount of methyl N-methyl anthranilate. 2,6-dihydroxybenzyl caproicacid
Many years later, Maurer and Hauser (1992) used a benzoate heptanoicacid
1H-NMR and MS to charac- methyl3,4- nonanoicacid
combinationofpreparative GC,
dimethoxybenzoate decanoicacid
terize (Z)-3-(1-butenyl)-pyridine in a sample of narcissus -butenyl undecanoic acid
3-methyl-2
a b s olut ein ppm lev e l s . benzoate dodecanoicacid
In 1993,van Dort et al. examinedthe chemical composi- dimethylphthalatet tridecanoicacid
tion of a selectionof l{arci.sstt'stozetta)l./.poeticusthat they dibutylphthalatet tetradecanoicacid
methylsalicylate pentadecanoicacid
called l/. geranium (a name that does not have universal palmiticacid
ethylsalicylate
taxonomic acceptance).Using a combination of fractional benzylsalicylate stearicacid
distillation,column chromatography,analyical and preptlra- 3-phenylpropyl salicylate linoleicacid
tive GC, GCiMS, IR and NMR they reported that the methylo-anisate linolenicacid
compounds identified in a volatile oil of the hybrid form of methylp-anisate oleicacid
methylvanillate (E)-cinnamic acid
narcissuswere as follows: acid
methylbutylcarbamate 3-methylcrotonoic
decane (E)-methyl
isoeugenol isopropylmyristate T-butyrolactone
unoecane p-cresylmethylether methylpalmitate Y-caprolactone
dodecane caryophylleneoxide isopropylpalmitate 4-methoxy-2,3-d imethYl-2-
'1,4-dimethoxybenzene methylIinoleate nonen-4-olide
tridecane
tetradecane 6,7-ocimene epoxide 2-methyl-2-butenol .,- r i n r {a n a lanlnna

n6 nt adaaana diphenyloxide 2-hexanol 6-octadecalactone

hexadecane dibenzofuran (E)-3-hexenol bovolide
han+rr{aaana p-nitroanisole heptanol dihydroactinodiolide
naphthalene 5,6-p-ionone epoxide hotrienol indole
1,3-dimethylnaphthalene cis-linalooloxide (furanoid) Ztridecanol oxindole
2,6-dimethylnaphthalene frans-linalooloxide (furanoid) octacadanol benzothiazole
diphenylmethane nyl-5-
cls-2.6,6-trimethyl-2-vi docosanol dimethylsulfone
fluorene hydroxyJ4itrahydrofuran benzylalcohol dibenzothiophene
limonene nYl-5.
tran s-2,6,6-timelhyl-2-vi
. correclisomernot identified;tanifacts
B-phellandrene hydroxytetrahydrof uran
(Z)-B-ocimene 2-hydroxy- 1,8-epoxy-P-menthane
It is a shame,r'vhenthe authors report such a detailed
(E)-B-ocimene (E)-anHhole
1,8-cineole m-cresol analysis,that they did not present any quantitative data on
methyleugenol p-cresol the individual con'rpounds.Nevertheless,they did present
(Z)-methyl
isoeugenol 4-vinylguaiacol some relative amounts of the individual compound classes.
Those amounts are summarizedas follows:
TableVl. Comparativechemicalcomposition(%)
aliphatichydrocarbons (0.9%) aldehydes(0.4%) of fab preparedabsolutesof Narcissus tazetta
aromatichydrocarbons(<1 %) ketones(0.1%) and N. tazetta spp. tazetta
sesquiterpenoids (<0.1%) acids(5.2%)
ethers(1.9%) lactones(0.2%) Compound N. tazetta N. tazetta ssp. tazetta
phenols(2.7%) N and S compounds(2.4%)
eslers (27.2o/o) o-ptnene 2.39 6.07
unidentified (48.2o/o)
alcohols(10.8%) 6-3-carene 6.57 8.40
limonene 2.15 3.25
The following yeat Bruno et al. (1gg4) compared the 1,8-cineole t.z +b 3.03
y-terpinene 27.21 10.29
chemicalcompositionoflab-prepared absolutesofN . tazetta
p-cymene 1.27 o.cJ
andN. tazetta ssp.tazetta,using capillary GC analysis.Their linalool 0.62 11.70
results are shown in Table VI. oterpineol 0.33 t.v5
Also in 1994, Arai isolated the volatiles from ly'. tazetta benzylacetate 9.58 9.53
nerol 0.51
aar. chinensis flowers using simultaneous distillation and
benzylalcohol 4.79 1.70
extraction.The resultantvolatile concentratewas subiected (E)-methyl cinnamate 5.84 1.13
to analysis by GC and GC/MS. A summary of the data (E)-ethylcinnamate 0.53 5.63
obtained from this analysiscan be seen in Table VII. In N-methylanthranilate 0.19 0.43
cinnamylalcohol 2.87 0.81
addition, the authors compared the results of this analysis indole 1.51
with those obtained from a headspaceanalysisof the same benzylbenzoate 4.00 0.65

Table Vff. Comparative chemical composition (%) of the volatiles and headspace ot Narcissus
tazettavar. chinensis
Compound Volatiles Headspace Compound Volatiles Headspace
isobutylacetate 0.03 phenylacetaldehyde 0.15 I
d-prnene 0 .1 4 y-terpineol 0.06 I
butyl acetate 0 .10 heptadecane 0.01
hexanal oo: 0 .0 1 d,terpineol 2.23 o.37
B-pinene 0.04 benzylacetate 24.14 19. 03
sabinene 0.04 geranytacetate 0.04
myrcene
isoamylacetate
0.03 0.99 (22,4E)-decadienal 0.03 l
o .1 2 (2E,4E)-decadienal 0.11 I
heptanal 0.7; t 2-phenethylacetate 0.92 1.53
limonene 0. 12 0.23 geraniol 0.04 I
1,8-cineole 0. 51 benzylalcohol 2 1. 0 0 0 . 15
(Z)-B-ocimene 0. 1I 0.60 2-phenethyl alcohol 0,57 0 . 01
(E)-B-ocimene 4.62_ 5 1 .19 (E)-cinnamaldehyde 0.05
hexylacetate 0.07 benzylcyanide 0.18 t
terpinolene 0 .1 0
octanol
I 3-phenylpropylacetate 1.83 ou :
0.09 2-phenethylbutyrate I
(Z)-2-pentenal o.02 ercosane 0.12
2-methyl-2-butenol 0.09 o t: methyleugenol o.o4
(Z)-3-hexenol 0.02 3-phenylpropylalcohol 1.52 0.04
nonanal 0.44 I methylcinnamate* I I
hexanol 0. 19 0. 14 heneicosane 2.35
(E)-2-octenal 0.02 o-methoxybenzyl acetate 1.42 0.03
2-ethylhexanol 0.05 benzyltiglate 0.12
tetradecane 0.08 o-methoxy-2-phenethylacetate 3.73 0.1;
cls-linalooloxide (furanoid) 0.05
aceticacid 0.04
t cinnamylacetate* 0.26 o ol
o-methoxybenzyl alcohol 0.25
frans-linalooloxide (furanoid) oo: t methylisoeugenol" 0.02
pentadecane
benzaldehyde
0.03 docosane 0.04 l
I I o-methoxy-2-phenethyl alcohol o.41 I
linalool
linalylacetate
6.24 6.30
0 .19
o-methoxy-3-phenylpropyl acetate o.76 o o1
I tricosane 0.84
octanol 0. 14 cinnamylalcohol. 0.'12 I
hexadecane 0"03 o-methoxy-3-phenlpropyl alcohol 0 . 1I
* t
bornylacetate 0.02 y-dodecalactone 0.53 I
terpinen-4-ol 0 .0 1 indole
methylbenzoate :
6.30 o o:
0 .0 1 penlacosane 2.14
citronellylacetate 0.03 benzylbenzoate 2.18
i, I
undecanal o.20' I heptacosane 0.65
(E)-2-decenal 0.05 t benzylsalicylate 0.17
-correctisomernot identjfied;t = trace (< 0.01%)
flor,ver collection. These results are also summarized in undecadienal and 2-butyl-(E)-2-octenal by synthesis,the
Table VIL authors also determined that (42,7Z) -decadienalpossessed
This same yeaa Ohloff reported that jasmone (pres.tm- an odor characteristicto that of the whole calamusoil.
ably cis-) was an importat odorous constituent of narcissus Two years later, Ramaswamiet al. (1988) used GC/MS
absolute. and Kovats indices to examinethe sesquiterpenehydrocar-
bons in calamusoil. In this study,the authors unequivocally
C.Yernj;l.Ddtection et daahtation del'antlranilate tle et desddriads characterizedthe presenceof the following:
rnethyles rlans dffirents dchantillon,s nafirels et de synthdse
par CCM et GLC. La France et sesParfums.,9,429-448 (1966) 6-cadinene B-sesquiphelland
rene
o(-catacorene B-gurjunene(calarene)
B. Maurer and A. Hauser , Neu pqricline cleriaatiaesfrom essential
o,-selinene
oiLs.Chimia,46, 93-95(1992).
H.M. van Dort, P. O. jagers, R. ter Hejde and A.J.A. van deer In 1990, Nisam et al. obtained an oil o{'calamus]n 4.57o
Weerdt, Narcissustretithian anr.l Nar cissusgeranium. Analysis yield from rooti harvestedin tbe vicinity of Haldwani (India).
and synthesis of comTxtuntk. J. Agric. Food Chem., 41. 2063- Using GCIMS as the method of analysis,the Nigam team
2075 (1993)
found that the oil contained:
S. Bruno, N. de Laurentis, A. Amico and L. Stefanizzi,Chemical
inDestigation nntl cytologic localization of essential oils in the 1,B-cineole (0.19%) methyleugenol(1.61%)
flotoers of Narcissrls tazetta. Int. J. Pharmacog., 32, 357-361 l i n a l o o(l0 . 1 9 %) o-asarone(1.17%)
(1ee4). terpinolene (0.19%) B-asarone(92.68%)
T. Arai, Volatile compounds of Narcissrts tozetta. Dar. chinensis crterpineol(0.09%) y-asarone(2.27%\

Jlouers. Koryo, (1fJ4),105-111(1994) Also in 1990,Lander and Schreierused a combination of

G. Ohloff, Scent andfragrances. Thefascination of orlors antl their GC/MS and GC-FTIR to analvzecalamus oil and extracts
chernical p erspectiDes. Translated b1'W. Pickenhagen and B. M.
originating from both triploid and tetraploid fbrns of A.
Lawrence, p. 223, Springer Verlag, Berling Heidelberg (1994).
calamus.The oils from the tetraoloid form of calamuswere
obtained comn'iercially. The oil Trom the triploid form was
CalamusOil steam distilled by Lander and Schreier. In addition, the
In 1979, Tanker and Sarer (see also Tanker et al. 1993) authors also performed Soxhlet extraction of cut calamus
reported that the components of the hydrocarbon {raction root usingdiethyl ether asthe solventto produce the extracts.
of an oil of Acorus calonurs of Turkish origin were as follorvs: The calamus oils and extractswere initiallv fractionated over
silica gel using gradient elution prior to GCI/MS and GC-
cx,-pinene(5.4%) limonene(1.4olo)
camphene(29.5o/o) (2.3%) FTIR analysis.The main componentsof the oils and extracts
B-phellandrene
B-pinene(3.9%) yierpinene(0.8%) of'calamusare found in Table VIII.
6-3-carene(7.0%) (Z)-B-ocimene (19.3'l") As can be seen from the results.the tetraoloid oils were
sa bin en e(1 .5% ) ( 3. 1% )
t er pinolene extremely rich in B-asaroneand contained no acorenon",
myrcene(1.5%) (E)-B-ocimene (4.6%)
while the triploid oil and extracts were devoid of y-asarone
o-terpinene(6.4%) p-cymene(3.9%)
but were rich in acorenone.The authorsrecommendedthat
Unfortunately, the authors did not present an)rdata on this data be used to determine the origin of calamus in
the proportion of hydrocarbonsor oxygenatedconstituents, processedfbods.
especiallythe toxic B-asaronein the oil. In 1991, Lander and Schreier examined the stability of
A number of years later, van Lier et al. (1986) examined o(-asaroneand B-asaronein ethanolicand aqueousethanolic
the aldehyde content in calamus oil of eastern European solutions. The importance of this study is that calamus is
origin. Using Girard P isolation of the aldehydes from a traditionally used in Europe to flavor alcoholic beverages.
fraction of calamus oil, which was obtained by fractional The authorsfound that when solutionsof both asaroneswere
distillation, the aldehydic fraction was fbund to contain: storedin the dark at ambient temperaturesfor sixmonths,no
hexanal (Z)-5-undecenal chemical transformationswere observed. However, when
no n a n a l undecenal* the solutions were stored in daylight, rapid isomerization
(E ) - 2 - n o n e n a l (42,72)-undecadenal of both asaronestook nlace. In fact. after six months no
decanal 2-butyl-(E)-2-octenal B -asarone t' oul dhe detectedi n the sol ul i ons.
t7\ A A^^^^^l
perillaldehyde
\4,/- a- uEU9r r al
Two years later, Li and Jiang (1993) used CC/MS to
(2E,4E)-decadienal p-mentha-1,3-dien-7-al
2,4-decadienal- cuminaldehyde
examine the composition of calamus oil produced from
(42,72)-decadienal anisaldehvde different plant parts ofA. calamuscollectedfrom tbe vicinity
decadrenal* B-cyclocitral of Shenyang (China). A summary of the results of these
undecanal 2,2-dime.thyl
bicyclo[2.2.1] analysescan be seenin Table IX.
(Z)-4-undecenal heptane-2-carboxaldehyde The fbllowing year, Motley (1994) reported a detailed
" correct isomer not identified. review of the usesand biological activitieso{ A. calomus.
In 1995,Bourrel et al. screeneda number of oils for their
In addition to confirming the structures of (.42,72)-
antimicrobial characteristics.Among theseoils u'asa sample
decadienal, (Z)-4-undecenal,(Z)-5-undecenal, (12,72)-
 Table Vlll. Percentage composition (%) of the resin components of calamus oils and extracts

Calamusoils Calamus extracts

Compound 1 2 3 4 5 6
pre-isocalamenediol 1 .0 1. 0 0.6 7.1 2.0 9.0
calamenediol 1. 0 2.0 2.0 1.0
isocalamenediol 11.3
shyobunone+ derivatives iu 6. 0 6.2 J.O 9.0 J.J

calamenene' 1 .0 0.5 0.9

acorenone i.o 18 . 1 7.5
acorone 5.6 6.1 10.5
isoacorone 1.3 t.3
B-asarone 8.4 55.0 +e.o 3.6 8.2 4.6
cx,-asarone 3 .7 3. 0 2.7 0.5 0.4 0.4
Y-asarone 1 .4 t.J 1.0
* correctisomernot identified;
samplesl-3 were oils f rom tetraploidA.calamusisamples4-6 were oil and extractsfrom triploidA. calamus

Table lX. Comparativechemical composition (%) of calamus oil produced from different plant parts

Leaf Rhizome Root Leaf Rhizome Root

Compound oil oil oil Compound oil oil oil
sabinene 0 .2 1 6-cadinene 4-07 3.72 1 .5 7
myrcene 0.09 acotamone 1.61 3.09 0.33
p-mentha-2-4(8)-diene 0.07 0,-catacorene 0.30 1.30 0 .6 8
p-cymene 0.04 elemol o.73 0.60
Iimonene 2 ,6 1 isoshyobunone o:o 0.08
y{erpinehe 0.05 B-calacorene 0.30
o-terpinene 0.04 epi-shyobunone o 1 8 .7 0
linalool 3 .1 0 0 .2 1 0.24 B-bisabolene o.21 :,
camphor 0.08 0.24 0.03 iso-epi-cubenol 1.81
borneol 0 .1 1 0 .1 1 0.04 isoacolamone a:, 3.25
terpinen-4-ol 0.21 0.22 0"08 preisocalam enedioI - 0 .9 1
o-terpineol 0 .3 1 0 .1 4 0.05 B-asarone 2.85 1 .6 8
linalylacetate 0 .1 1 o-muurolol 2.60 1. 1I 0 .6 9
h ^ "^ .,1
u vil ryr ^^^+ ^+ E
dugLat ^ 0.25 o.o4 epi-o-muurolol 3.17 1.70 0 .2 4
6-elemene 0 .2 1 (1,10)-aristolen-2-one 6.57
3,3,T,9tetramethyltricyclo 8-hydroxy-6-cadinene 2.48
[5.4.02,8]undecene- 0.13 catamusenone o.72 0.73
0-santalene 0.01 1,6-dimethyl-4-isopropyl-
c{-copaene 0.04 0.07 0.05 naphthalene - 0.45
p-bourbonene 0.05 calamenene* o . ro 14.7 3 .1 5
cr-ceorene 0.61 1,4-dihydro-1,
1,4,4-tetramethyl-
p-elemene 0.79 0.48 o?n 2,3-naphthalenedione 0.230 0.59
methyleugenol 0.86 0.56 acorenone 0.24 1 .0 9
p-caryophyllene 4 .1 3 0 .3 3 8-hydroxy-6-cadinene 0.80
a-humulene o?' cadala-1 ,4,9-triene 2.46 0.64
&cadinene _ o.'44 2-isoproponyl-6-isopropyl-
fcadinene 2.11 methyl-3-vinylcyclo-
cascarilladiene 1.43 hexanol - 0.35
p-gurjurene I o.tt 7.66 tsocalamenediol o:' 8.37
(E)-B{arnesene 1.12 calamenediol 0.86
1Z)-methyl isoeugenol 36.40 17.70 2.85 catamenone 0.60 9.62
p-cubebene 0 .3 2 0 .1 4 dibutylphthlate.. o-4 - u. t5
calarene+ 0 .9 6 0 .1 2 palmiticacid 0.06 - 0"05
snyoDunone 3 .1 9 5 .0 3 1-octadecene 0.04
iE)-methyl isoeugenol 3.37 0.29 phytol 0.11
2.6.10,10-tetramethyl{ricyclo linoleicacid 0.02
f7 ) (\ O46l9ttndaoana* _44 0 . 16 methyl9,12,1 S-octadeca-
acoradiene* 0.35 trienoate 0.04
ar-curcumene 0-74 tflcosane 0.10
3-guaiene o.ao. o.go 0.11 7-desmethyl-2-methoxy-
E. E)-uJarnesene 0.30 cadalene 0. 09
,r:r-mUUfOlene 0.96
acoragermacrone 4.09 7.38 0.50 ." anifact
' correctisomernot identified;+ also knownas B-gurjunene;
of calamus oil, which on GC/MS analysis was found N. Tanker and E. Sarer, On the monotherpene hydrocarbons of
Turkish calamusoil. J. Fac. Phar. Ankara, 9, 60-63 (1979).
contain:
B. M. Lawrence, Pro gress in essential oi'ls.Perfum. Flavor.,5 (6 ), 49-
linalo ol(0 .1% ) methylisoeugenol- (1.0%) 55(1e81).
carvacrol(0.1%) spathulenol(t)
F. P. van Lier, L.M. van der Linde and A. J. A van der Weerdt,
B-caryophyllene (t) (Z)-B-asarone (92.0%)
Isolation and synthesis of Qz,7Z)-decadienal, the character
isoe ug en ol.(1 .0% ) (E)-B-asarone (1.0%)
impact compound of the oil Acorus calamus L. In Progress i_n
acoradiene- (1.0%) o-eudesmol(0.5olo)
essentialoil research.Edit., E. J. Brunke, pp.216-225,Walter de
6-cadinene (0.4%) palmiticacid (0.3%)
Grulter Co., Berlin (1986).
- correct isomer not identified S. K. Ramaswami,P. Briscese,R. J. Gargiullo and T. von Geldern,
t = tra ce (< 0 .1 %)
Sesquiterpene hydrocar:bons:from mass confusion to ord,edtl
Also in 1995, Todorova et al. examined the chemical lirrc-uyt In Flaaors and F ragrances: AWor:ld Perspecfioe. Edits.,
B. M. Lawrence,B. D. Mookherjeeand B. J.Willis, pp. 95f -980,
con'rposition of calamus root oil produced from plants
Elsevier SciencePubl. 8.V., Amsterdam (1988).
collected in the eastern Mongolian province of Buymur/
M. C. Nigam, A. Ahrnad and L. N. Misra, GC/MS e\amirtotion of
Halhim Gol. The analysiswas performed by using a combi- essential oil of Aconts calamus. Indian Perfum., 34, 282-285
nation of capillary GC (retention indices) and GC/MS. The (leeo).
con'rpoundsidentified in Mongolian calamusoil were: V. Lander and P. Schreier.Acorenoneandy-asarone:indicators of
(1.3%) the origin of cnlamas oi,ls(Acortrs calamus L.). Flav' Fragr. j., 5,
a-pinene(0.7%) 8-cadinene
camphene(0.5%) camphor(1.5ol.) 75-79(r9e0).
B-pinene(0.9%) linalool(1.3%) V. Lander and P. Schreier,Li ghtinducedtransformationr,fasarr,ne-
u-phellandrene (0.2%) bornylacetate(4.6olo) Flav. Fragr. J., 6, 21-28(1991).
myrcane(0.7%) terpinen-4-ol (1.1%) M. X. Li arrdZ-B .liang, The datile constituents of tha essentialoil
a-terpinene (0.4%) 6-epi-shyobuno ne (3.7"k) and their distribution in AcoruscalamusL. Zhotgcaoyo, 21, 459-
limo ne ne(1.1 % ) shyobunone(0.5%) 461 (1993).
1,8-cine ole(1.1 % ) isoshyobunone (13.1'/')
preisocalamenediol (12.1%) M. Tanker, N. Tanker, E. Sarer,E. Atasu,B. Senser,S. Kuruci and
(Z)-B-ocimene (0.6%)
(0.8%) F. Mericli, Resultsof certain inDestigations on the aolatile oil
(E)-B-ocimene (0.8%) (E)-methyl isoeugenol
containingplants, Irr: Proceedings tf the IF EAT meeti ng. Antalya
6-elemene(0.5%) acorenone(14.4%)
1990. Ediii., K. H. C. Baser and N. Giiler, pp. f6-19, Istanbul
o-copaene(0.3%) o-cadinol(0.7%)
(1.0%) calamusenone (0.5%)
(ree3).
o-bergamotene.
B-elemene (0.5%) calamenediol (1.4%) T. J. Motley, Theethnobotantlof su;eetflag,Acoruscalamas(Araceae).
(E)-B{arnesene (1.0%) isoacorone (5.7%) Econ. Bot., 48, 397-412 ( 1994\.
cr-selinene(0.7%) acorone.(0.9%) C. Bourrel, C. Vilarem, G. Michel andA. Gaset,Etudedespropridtds
* correct isomer not identified
bacteriostatiqueset fongistiques en milierr 'solidede 24 huiles
essentiellesprda.mblimentanaly,sees. Rivista Ital. EPPOS, (16),
3-12(19e5).
The absenceof B-asaronein this Mongolian oil of calamus M. N. Todorova, I.V. Ognyanov and S. Shatar,Chemical comp osition
suggeststhat itwas produced from the diploid form (Lawrence of essentialoil from Mongolian Acorus calamus L, rhizomes. l.
1 9 81) . Essent.Oil Res.,7, fgf-193 (1995).

122
Progress in Essential Oils
Reprinted
f romPerfumer
& Flavorist,
May/June
1997, Yol.22, No.3, P. 57

RoseOil acetone(0.016-0.041 %) benzaldehyde(0-0.10B%)

ethyl acerate(0.096-0.356%) linalool(0.530-1.2490/"\
In 1981, Takahashiet al. reported that Bulgarian rose oil ethanol(2.310-5.1B2o/o) cx-guaiene (0.833-1 .179%)
containedgermacreneD (0.3IEo)and mint sulphide(0.0I % ). pentanal(0.057-0.143%) terpinen-4-ol(0.271 -0.451"/.)
Eight years later, Xue et al. (1989) used CC (retention 2-butanott(0.13-0.25%) hexadecane(0.061-0.076%)
indices) and GC/MS to analyzethe oils produced from roses cr-pinene(O.416-1.071o/") citronellylformate
isobutanolt(0.024-0.07 9o/") (0.023-0.036%)
of different taxonomic origins grown in different locations in
B-pinene(0.104-0.217o/o) citronellylacetate
China. Rosa ru,gosaThunb. was grown in three areas,and a sabinene(0.037-0.085%) (0.292-0.360%)
hybrid ofR. setuta andR.rugosainone of the areas,although butanol(0.009-0.01 6%) s-humulene (0.628-0.7 29%)
the authors did not indicate in which area the hybrid rose 2-propenol.(0-0.009%) nercl (0.423-0.723"/"\
was grown. The components identified in these four rose oils myrcene(0.183-0.453%) uterpineol (0.153-0.320%)
o,-terpinene (0.006-0.026%) y-muurolene(0.476-0.902%)
are shown in Table I.
heptanal(0.075-0.203%) 6-guaiene(0.349-0.525%)
In 1992, Basernoted that village-styledistillation ofrose 2-methylbuianol heptadecane(1.079-1.642"/")
oil in Turkey takes place in copper or galvanized steel open- (0.166-0.393%) geranial(0.633-1 .009%)
fire stills having a capaciq/of 150-1,000L. (Most stills have 1,8-cineole (0.009-0.01 4%) heptadecene*(0.120-0.256'/.)
a 300 L capacity.) The stills consistofa pot (or retort) and 2-hexenal*(0-0.01 1%) geranylacetate(0.668-1.215%)
2-amylfuran(0-0.007%) citronellol(35.832-43.545%)
a removablesphericalhead that is connectedto a pipe (the
(Z)-B-ocimene (0-0.012%) nerol (5.266-6.249%\
condenser) that leads through a pool of lukewarm water. At amyl alcohol+ y-terpinene octadecane+ 2-phenethyl
the end ofthe pipe is usually a 9 L glasscollection vessel.In ( 0 . 0 6 0 - 0 . 111%) acetate(1.027- 1.822o/")
a typical village distillation, 10 kg of fresh flowers and 60 L of (E)-B-ocimene (0.012-0.0369.i geraniol(10.182-13.447%)
water are added to the 300 L still. It takes 1-2 h to set 18 L p-cymene(0.015-0.068%) 2-phenethylalcohol
terpinolene(0-0.029%) ( 1 . 0 7 8 - 1 . 9 8 9 %)
of condensate water. Because of the low oil yield fiom the
(E)-3-hexenol(0-0.009%) nonadecane(7.692-9.835%)
condensatewateq ca. 60 L are collected and redistilled 6-methyl-5-hepten-2-one (92)-nonadecene (2.189-2.729"/")
yielding approximately 18 L of condensate.The oil decanted (0.019-0.047%) methyleugenol+ eicosane
from this second distillation is referred to as village or rural cis-rose oxide (0.570-0.747%) (3.250-3.795%)
oil. It is ofinterest to note that after the oil hasbeen decanted trans-roseoxide (9E)-eicosene(O.122-0.445%)
( 0 . 1 5 8 - 0 . 1 9 9 %) (Z)-nerolidol(0.054-0.1 32%)
from this condensate, it is diluted with distilled water and
(Z)-3-hexenol (0.038-0.050","/ heneicosane(2.603-3.27 8%)
sold as rose water. hexylmethylether (0-0.008%) (5E)-eicosene(O.083-0.1 47%)
The [.pical capacities of factory oil production are 400- nonanal(0.039-0.089%) eugenol(0.354-1.266%)
500 kg of fresh flowers and 1,500-2,000L of warm water 6-methyl-5-hepten-2-ol decosane(0.055-0.104%)
charged into a copper or stainlesssteel still pot (generally (0.020-0.023%) tricosane(0.408-0.688%)
pentadecane(0.270-Or'25%) (E,E)-farnesol(0.332-0.427'/")
3,000 L capacity). Steam is introduced into the bottom of
the still pot. With the condenserskept at 35" C, distillation
usuallytakes1.5h. The condensate,which is separatedin the t tentativeidenti{ication

200 L stainlesssteel collection vessels,comprises a large
volume of water and a low volume of oil. The oil that is
decanted from the condensate is known as crude oil, first oil
or direct oil. Once the oil has been separated out, the
condensatewater is pumped into stainlesssteel holding
tanks.The condensateis then redlstllled in 3,000 L stills to
ield more rose oil, although this oil is known as second oil,
cookedoil or indirect oil. At the end of the distillation season,
the first and secondoils, which havebeen sbred in the dark
in glass,are mi-xedtoyieldTurkishroseoil In someinstances,
village oils are blended with factory oils.
Analysis of Turkish rose oil by GQIMS (Baser 1992)
revealsthatbetween 1989and 1990,oils from fourproducers
were fbund to vary as follows:
Baser also compared the major component composition
ofvillage-producedoils (four samples,1987-f990)\'ith those
produced in the factory (20 samples,f986-1990).The results
of this comparativestudycan be seenin Table II. In addition,
a comparisonof the compositionof a |pical blend ofvillage-
and factory-produced oils can be seen in Table IL Finally,
Baser compared the major components of oils produced
from {resh flowers with those nroduced from fermented
flowers. These results are found in Table IIL If the
citronelloVgeraniol ratios for oils produced from fresh and
fermented flowers are compared, the following is obtained:
freshflower oils:7.01-7.07
fermentedfloweroils:6.86-14.96
 of rose oil produced from roses grown in different parts of China
Table l. Chemicalcomposition (o/o)

Compound 1 234 Compound 1 234

iurfural I ttt (Z)-B-farnesene I ttt
2{urfurol I ttt calamenene' t ttt
(Z)-3-hexenol t ttt allo-aromadendrene 2.1 0.4 3.7 1. 3
tti T-muurotene 0.8 0.3 1.0 0. 4
hexanol I

t ttt 2tridecanone 2.1 0.5 2.5 1. 1

2-heptanol
ttl 2tridecanol 0.8 o.4 1.3 0. 5
benzaldehyde I
(I-prnene t ttt cx,-himachalene u.3 0.2 0.7 0. 2
heptanol t ttt y-cadinene I t tt

6-methyl-5-hepten-2-ol I ttt (Z)-nerolidol t ttt

1 ttt 6-cadinene t ttt
F-pinene 0. 1
(Z)-3-hexenylaceate I ttt elemicin 0.2 o.2 0.2
t ttt caryophylleneoxide o.4 0.3 0.7 0. 4
hexylacetate
ttt 2-tetradecanone 0.3 0.2 0.3 0.3
benzylalcohol
ttt (E)-nerolidol 0.2 0.2 0.3 0. 2
(E)-B-ocimene
isooctylformate ttt ledol t t0.4t
alcohol t it t caryophyllenol- 0.7 0.5 0.4 0. 6
1,1-dimethylbenzyl
t t I t B-eudesmol 0.4 0.2 0.6 0. 3
linalool
1 .4 2 .0 t.o 0.B 2,3-dihydrofarnesol I t 0.5 0. 2
cis-roseoxide
0 .1 0 .2 0 .3 25.1 (Z,E){arnesol 1.1 0.8 1.3 0. 6
2-phenethylalcohol
0.3 u.:) 0 .7 0.4 2-pentadecanone 0.5 0.2 0.7 0.4
trans-roseoxide
0 .2 0 .8 0 .2 0.2 2-pentadecanol 0.2 o.2 0.4 0. 2
citronellal
o.4 0 .6 0 .4 0.2 h o n l .a l a ^ a n a 0.2 0.1 0.2 0. 2
o-terpineol
49.2 cI.l 5 1 .0 JI.I (E,E){arnesol 2,9 2.3 3.1 1. 5
citronellol
t t I l.
caryophyllenol 0.7 0"1 0.6 0. 6
nerol T

t t (Z,E)-farnesol 0,2 t 0.2 0. 2

2-phenethylacetate I I

geraniol tJ. / t,l 1. 0 9.0 (E,E){arnesol I ttt

t t t benzylbenzoate 0.3 0.4 0.6 0. 2
geranral I
I t octadecane I 0.2 0.2 0. 7
citronellyl{ormate I I

t t t nootkatone I 0.2 0.2 0 .6

2-undecanone I
2-undecanol t I I I 2-heptadecanone t t it
3 .7 2 .3 2 .5 3.0 2-heptadecanol I t tt
citronellylacetate
I I nonaoecane 0.4 0.3 0.5 0 .4
nerylacetate I I

eugenol 0 .6 0 .3 0 .2 0.7 hexadecanoicacid I ttt

0 .3 0 .8 0.4 0.3 ercosane 0.2 0.2 0.2 0. 2
geranylacetate
methyleugenol 1 .6 J.+ 2 .6 2.3 (E)-4-acetoxycinnamyl
cx-copaene I I t I alcohol t I

I heneicosane 0.9 0.7 1.1 1-2

2-dodecanol
o.2 oocosane 0.1 i 0.1 t
aromaoenorene
o.2 tricosane 1.2 0.9 1.4 1 .2
cr-bergamotene.
t tetracosane 0.1 I tt
cI-santalene
n 6 n ta n d e tn a 0.6 0.4 0.6 0 .6
ethylcinnamate I

L" s " , . d . @ n s u p r o v i nce ;2 = Pin g yin in Sh a n d o n g p r o Vin ce;3=Ledui nQui nghai provi nce;4=Lanzhoui nGansuproV i nce
* correctisomernot identified
t = t r a c e( < 0 . 1 % )

camphor(trace) 2-phenethylacetate(0.36%)
Using a closed-loopstripping procedure on living roses, ne (17.39%)
rane (7.41%)
frans-theaspi dihydro-B-iono
the headspaceof three cultivars was examined by Brunke et e (0.28%) 3,5-dimethoxytoluene(50.30%)
B-caryophyllen
al. (1992).Resultsof GC/MS analysisof the desorbedflower methylbenzoate(0.36%) 2-phenethylalcohol(2.76%)
volatiles can be seen in Table IV. In addition, the authors 4-vinylanisole(1.97'/.) (3.42%)
dihydro-B-ionol
reported that the headspacecomposidtlnof aliving cultivar
- correct isomer not identified
(Queen Elizabeth) of a hybrid roservasfound to contain: t = tr ac e ( < 0.01% )

o-pinene(0.57%) (Z)-3'hgxenylacetate(1.17%) It is of interest to note that both the cultivar rosesand the
hexanal(0.56%) (0.35%)
6-metliyl-5-hepten-2-one hybrid rosepossessed headsPace compositionsthat were ven
limonene(O.28%) hexanol(0.39%)
(Z)-3-hexenol(0.21%) cliff'erent from each other. These types of di{ferences in the
2-hexenal-0.54%)
hexyl acetate0.38%) clstheaspirane(9.38%) compositionof different rosesiswell l<nown(cf.Lawrence1991)'

124
 Table ll. Comparativechemical composition (%) Table lll. Comparativechemical composition (o/o)
of Turkish village-and factory-producedrose oils, of Turkish rose oils produced from fresh flowers
and a village/factory blend and oils produced from fermentedflowers

Compound Villageoils Factoryoils Blend Fresh flowers Ferments flowers

ethanol 0- 1. 67 0. 50- 5. 18 Compound 1st oil 2nd oil 1stoi l 2ndoil
monoterpenehydro-
monoterpenehydro-
carDons 0. 15- 1. 31 0.80-2.71 0.578
carDons 3.86 0.27 1.78 0. 33
nonanal 0-0.04 0.03-0.09 0.054
nonanal - 0.04 0.07 0.05
linalool 0.85-2.01 0.53-1.27 0.802 linalool 0.20 1.23 0.40 1. 62
citronellylformate+
citronellyl
formate+
citronellylacetate 0.19-0.34 0.24-0.54 0.277
citronellylacetate 0.80 0 . 1I 0.80 0"1I
o-terpineol 0.20-0.53 0. 13- 0. 46 0. 2 1 2
cI'-terpineol 0.03 0.03 0.05 0.35
geranylacetate o.74-2.54 0. 55- 1. 67 1. 1 6 4 geranylacetate 2.67 0.23 0.35 0. 16
citronellol 25.04-38.97 30.67-45.83 35.645
citronellol 29.60 50.90 31.26 58.85
nerol 7. 50- 13. 36 4.52-8.89 7.785
nerol 2.58 3.90 1.55 5. 36
geraniol 20.05-31.80 8. 50- 16. 65 19.0 8 9
geranrol 4.22 7.10 2.49 8.58
2-phenethyl
alcohol 1. 85- 3. 55 1. 16- 2. 60 2-phenethyl alcohol 0.67 1.15 o.82 1. 77
methyleugenol 1. 40- 2. 67 1.93-3.37
(E,E){arnesol 0.44 0.19 0.30 0-14
/F tr\-fa rnacnl 0. 43- 1. 32 0.24-0.64 0.580
stearoptenes 12"20-9.1 83 14.00-25.96

Also in 1992, Sood et al. reported the resultsof a GC/MS In comparison, Ravid et al. (1992) determined that the
analysisof rose oil produced from R. damascenagrown in chiral distribution of citronellol isolatedfrom a commercial
Himachal Pradesh(India). The compoundsidentifiedwere sampleof Bulgarian rose oil in the relative amount of 23.67o
as follows: was found to be (R)-(+)-citronellol (267o) and (S)-(-)-
hexanol(0.25%) methyleugenol(1.90%) citronellol (74E").Theseresultsindicatethat the commercial
heptanal(0.21%) B-caryophyllene (0.25%) sampleof roseoil examinedwasprobably adulterated,based
o-pinene(0.65%) cr-cadinene(0.40%) on the previous findings of Kreis and Mosandl.
(0.1 5% )
B -p ine ne docosane(0.39%) The following year, Ma et al. (1993) used a combination
myrcene(0.220/4 heptadecane (1.83%)
2-phenethyl alcohol(4.06%) of GC/MS and retention indices to determine the comoo-
farnesol*(0.98%)
cls-roseoxide (0.68%) tridecane(0.22o/o) sition of rose oil produced from roses grown in Lanzhou
frans-roseoxide (0.29%) 9-eicosene*(2.65%) using Bulgarian, French, Turkish and Moroccan rootstock.
terpinen-4-ol (0.18%) nonadecane (12.30o/o) Then Ma's team compared these results with their own
o-terpineol(0.32'/.) eicosane(1.35%) determination of the composition o{ rose oils imported
citronellol(40.00%) tetradecanol(0.29%)
2-phenethylacetate(0.35%) from the same countries. The results of these analysesare
heneicosane (6.69%)
geraniol(14.49%) tricosane(1.69%) surnmarizedin Table V Both the oil produced from French
citral.(0.71%) octadecane(0.53%) rose rootstock and the imported French rose oil (obviously
eugenol(1.57o/") pentacosane(0.83%) Rosa centifulia) .rere {bund to possessan unusually high
geranylacetate(0.94%)
trans-rosecontent. It is the belief of this reviewer that this
determination is in error because the /rans-rose oxide
content oI'R. centfolia is usually ca. <0.IVo.
This sameyear,Kreis and Mosandl (1992)reported on the
The vacuum headspaceof R. dama,sena(CY. rose de
clirect simultaneousenantioselectivemultidimensional gas
resht) u'as analyzedby Surburg et al. (1993) using GC/MS.
clrromatographyofcis- and trans -rose oxide,linalool, can/one
The compositionwas found to be:
and citronellol. They used a heptakis (2,3-di-O-acetyl-6-
O-tert.butyl-dimethylsilyl)-B-cyclodextrin: OV-1701(50:50) 2-phenethanol (37.4-38S%)B-eudesmol(0.13-0.14%)
rapillary column after preseparationon a polar (Carbowar) geraniol(29.8-35.6%) geranyl (0.59-0"84%)
acetate
ci tronel l ol (0.71-1.1% ) (Z)-8-heptadecene( 0. 40- 0. 51%)
rapillary column. The authors found that the enantiomeric
B-elemene (0.12-0.19%) heptadecane (0.59-0.73%)
distribution of the five pairs of enantiomers in authentic elemol(0.95-1.25%) (Z)-9-nonadecene
(1.3%)
- 4*'
rose oil was as follows: s-eudesmol (0.20-O.21%) nonadecane(1.5-1.6%)
oxide(99.5%)
r+)-(2R,4S-crs-rose : (-)-(ZS,+i)-cls-rose
oxide(0.5%) The same authors also compared the composition of a
- t-(2R,4R)- oxide(99.5%)
trans-rose : (+)-(2S,{g)-trans-rose
oxide(0.5%) rose cultivar (fragrant cloud) headspaceproduced by both
(-)-(R)-linalool
(50%): (+)-(S)-linalool
(50%) a static (vacuum concentrate)and dynamic method with an
(+)-(R)-carvone
(0%): (-)-(S)-carvone
(100%) oil produced by a Likens-Nickerson SDE apparatus.The
(+)-(R)-citronellol
(1%): (-)-(S)-citronellol
(99%) results of this studv can be seenin Table VI.
 Table lV. Comparative chemical composition (o/dof the headspace of three cultivars of rose

Rose cultivar Rose cultivar

Lichtk6nigin Duchess of Lichtkdnigin Duchess of

Montebello Othello Compound Lucia Montebello Othello
Compound Lucia
0.06 5.84 0.35 camphor 0.31
o-pinene
0.03 linalool 0.04 :u'
butylacetate 0.07
0.03 0.09 hexadecane 0.40
camphene :
0.05 terpinen-4-ol 0.06
nexanal
undecane i.ro 0.06 B-caryophyllene 0.92 4.29 i uo
1. 27 0.22 methylbenzoate 0.93 0.84 0.53
B-pinene 0.02
methylgeranate 0.10 0. 07
isoamylacetate 0.46
2.O2 citronellylacetate o.29
sabinene
o.oo ethyl benzoate 0. 10
butanol
7.62 0.03 neral 0.12 1. 16
myrcene 0.16
0.17 g-humulene 0.27 0.25
amyl acetate 0.73
0.05 methylnerate 0.66
isoamylalcohol 0.20
io, 0.18 heptadecane 0.59 0.20
limonene 0.08
0.08 nerylacetate 0.25 0.34 0.34
p-phellandrene
'I Q- ninanle 0 .0 6 benzylacetate 0.07 --
0.07 germacrene D ),o,
amylalcohol
0 .10 o.ao geranial o.14 0.29 2. 26
hexylacetate 11. 40
o .2 3 1.81 ()[-muurolene - 0. 19
p-cymene 3.37
0.10 geranylacetate a.to 0.62 0.07
isoamylvalerate 0.06
citronellol 6.02 11. 64
4,8-dimethylnona-1,3,
0.27 methylsalicylate 0.21
7-triene'
(Z)-3-hexenylacetate 9.26 o.ot 1.10 nerol i.o, 3.83 21.70

2. 79 2-phenethylacetate 37.32 6.90

(E)-2-hexenylacetate
0.08 0.06 geranrol 2.56 0.20 29.86
6-methyl-5-hepten-2-one
0. 60 U.ZJ benzylalcohol 0.20
hexanol
o.ou 0.07 2-phenethylisobutyrate 0.20 o.14 0. 12
cls-roseoxide
0.07 0.17 nonadecane 0.18 0.86 0.28
(Z)-3-hexenol 0. 09
2-phenethylalcohol 12.83 30.46 0.20
(E)-2-hexenol 0.32
0.05 o.72 nonadecene* 1.85 - t.Yc
perillene
0.08 0.12 benzaldehyde
4-isopropenyl - 0 .1 6
styrene
cr-p-dimethyl 0.49
hYdrate 0 .1 3 B-ionone" 0.37
frans-sabinene 0.08
0 .11 eicosane -
neroloxide
0 .1 2 o.to p-anisaldehyde 0.12
octyl acetate
na nt r daar na 0 .3 8 hexyl benzoate o.ua -
u. to heneicosane 0.24 1.29 0 .4 4
c{,-copaene
o.07 9.13 benzylbenzoate 0.35
benzaldehyde

* correctisomernot identilied

citronellol(4.82%) geraniol(0.47%)
A Chineseoil of the Crimson Glory cultivar ofR chinensi's benzothiazole(2.81%)
n e r o l( 1 . 1 0 %)
u,assubjectedto GC/MS analysisbyZhu. et al. (1993) The
componentsidentified in this uniquely Chinese oil were: Also in 1993, Zhu et al. used GC/MS to analyze a flower
nonane(0.35%) 1-ethenyl-3-ethyl-benzene ol R. rugosa produced rn Mentougou (China). The com-
pentanal(0.20%) (0.56%) pounds identified were:
decane(0.35%) cx,-copaene (1.44'/.)
4%) 2-heptanol(O.21'/.) rhodinylethef - (0.24%)
B-pinene(1.57%) cr-pinene! .1 (0"10%) isorhodinylether""(0.10%)
myrcene(0.53%) butylacetate(0.13%) cr-pinene
camphene(1.05%) benzaldehyde (0.10%) benzylacetate(0.10%)
limonene(12.07%) (O.29%)
linalool(3.18ol.) B-pinene(0.10%) cr-terpineol
(E)-B-ocimene (1.96%)
linalyl4petate(14.98%) 6-meihyl-5-hepten-2-one citronellol(44.46%)
hexylacetate(3.95%)
lene (4.55'k) ( 0 . 1 0 %) 3,7-dimethyl-3,6-octadienol
(Z)-3-hexenylacetate B-caryophyl
benzylalcohol(0.10%) ( 0 . 1 0 %)
( 1 .13 % ) citronellylacetate(0.55%)
linalool(1.05%) geraniol(12.77%)
hexanol(3.17%) methylgeranate(0.13%)
geranial(0.65%) nonanal(0.10%) geranial(0.65'l.)
p-methoxytoluene (9.88o/.)
 Table V. Comparative chemical composition (%) of various rose oils produced from roses
grown in China (a) and rose oils imported into China (b)

Bulgarianrose Frenchrose Turkishrose Moroccanrose

Compound a b a b a b a b
isoamylalcohol 0 .0 1 0.03 o.02 0.01 0.05 0.02 0.06 0.02
amyl alcohol 0.02 0 .0 1 0.02 0.02 0.01 I 0.04 I
hexanal 0 .0 3 0.02 0.04 0.05 0.02 1 0.09 I
(Z)-3-hexenol 0 .0 1 0.03 0.04 0.04 t t 0.04 0.06
hexanol o.26 0 .2 3 0.10 0.12 0.08 0.11 0.48 0 .1 8
heptanal 0.09 0.06 0.04 t 0.08 I t I
0,-prnene 0.38 0.26 0.06 0.06 0.5 0.11 o.25 0.07
3-octanol 0.06 0.02 0.02 I 0.05 I I t
6-methyl-5-hepten-2-one 0.50 0.60 0.09 I 0.06 I I I
sabinene 0 .1 8 0.06 0.01 I 0.16 I I I
p-cymene 0.09 0.05 o.21 0.05 0.05 I I I
limonene 0 .1 3 0.28 0.30 0.44 0.07 t 0" 31 0.04
linalool J. t+ 2,90 1.87 '1.91 0.86 0-72 0.83 2 .1 0
cls-roseoxide 0.32 o .2 1 t 0.17 0-43 0.16 o.21 0.22
frans-roseoxide 1. 39 1 .2 6 17.55 17.88 2.11 1.77 2.66 J.OU

2-phenethylalcohol 0. 13 0 .1 0 0.10 I o.22 0.07 0.17 0. 12

perillylalcohol 0.05 0.04 0.18 0.08 0.08 I 0.21 0.04
terpinen-4-ol
rv,
H,,,v, I T o. 41 0.36 0.11 0.07 0.41 0.31 0.13 0.26
I 0,{erpineol 0.94 0.98 o.B7 0.88 0.18 0 . 1I I 0.62
citronellol 38.22 38.38 19.49 20"48 47.46 47.70 J | .O\t 33.82
nerol 0.05 0.06 I 0.31 I 0.41 I I

geraniol 14.41 1 9 .9 2 I o.+o 21.83 12.52 12.45 13.40 27.82

citronellylformate 0. 13 0"11 3.81 0.06 0 . 1I 0.35 0.08 0.02
geranylformate 0.06 0.05 0.11 0.22 t t
citronellylacetate 0.45 o.44 0.08 0.04 0.72 0.70 0,58 0.26
eugenol 0.82 0.82 1.98 2.28 0.73 o.29 0.56
vEr ar ryr dug(dtE 0.74 0.72 0.49 0.49 1.03 0.97 1.72 0 .8 1
p-farnesene* 0.20 0.20 0.34 t 0.01 t I t
methylisoeugenol. 1. 71 1 .7 6 0.47 '1.54 2.57 2.40 I 1 .3 5
p-elemene 0.08 0.06 t I 0.09 I I 0.06
p-caryophyllene 0.77 0.69 0.06 0.29 0.59 0.35 0.35 I
c(-guarene 0.50 0.42 0.05 t 0.46 o.32 I 0. 31
a-humulene 0.37 0.35 0.03 0.05 0.36 0.25 t 0 . 23
p-selinene 0"53 0.50 0.17 I 0.72 0.44 0.18 0. 42
p-bergamotene. 0. 17 0 .1 7 I I 0.12 0.20 0.33 0 . 10
pentadecane 0.70 0.77 I 0.20 0.71 0.53 0.49 0.43
ct-muurolol 0.08 0.09 0.05 I I I t 0.08
eudesmol* 0.07 0 .1 0 0.10 0.13 I I t 0 . 12
nardostachyol** 0. 17 0.28 0.04 I 0.12 0.16 t 0 . 12
rZ.Z)-farnesol 0. 21 0.22 0.27 0.27 0.27 0.23 0.23 0.22
"]eptadecane 0. 19 0.22 1.78 2.03 0.21 0.22 0.13 0 . 09
E.E)-farnesol 1. 98 2 .1 8 0.62 0.61 z,o I 2.24 3.04 1. 96
7-isopropyl-1
,8-
climethylnaphthalenone** 1. 12 . - 1 .0 5 0.06 t 0.59 0.67 I 0.72
senzyl benzoate 0. 10 0 .1 0 0.04 I i I tt
\r
' :onect isomernot identified
* Jncorroborated
rose oil component
: = n-ace(< 0.01%)
 geranylformate(0.15%) B-cubebene (0.96%)
2-undecanone (0.33ol.) ar-curcumene (0.14%) Table Vl. Comparativechemicalcomposition (%)
2-undecanol (0.51%) 2tri decanone (3-32'/.) of the headspace and oil of a rose cultivar
acetate(0.7B%)
citronellyl 2tridecanol(1.12'/.)
eugenol(0.98%) nerolidol-(0.14%) Static Dynamic
geranylacetate(0.78'/.) 2-pentadecano ne (1.22%) Compound headspace headspace Oil
2-dodecanone(2.48o/") (Z,E){amesol(0.91%)
(Z)-3-hexenyl
acetate 0.4 1O.O 0.2
methyleugenol(0.10%) farnesol*(3.76%)
2-phenethanol 45.0 15.0 41.0
o-bergamotene. (0.10%) benzylbenzoate(0.40%)
citronellol 5.0 5.0 5.0
aromadendrene(2.49%)
citronclhrl
a.ctate 0.4 5.0 0.8
. correctisomernotidentified
.. identityo{ thesecompoundsis uncenain 2-phenethylacetate 4.O 20.0 3.0
dAr en\r f r .Al r l o 2,0 - 4.0
Using both GC and GC/MS as their method of analysis, geraniol 16.0 - 1 .0
Bavrak and Akgtil (1994) examinedthe composition of two roseoxide* 0.1
hpes of rose oil produced at di{ferent factories (different B-damascenone - - 0.01
locations)in Turkey over tlvo distillation seasons.One was a
" correctisomernot idenlified
decirntedoil, distilled from fresh petals,while the other was
a blended oil distilled from paled (fermented) petals.Tables

Table Vll. Comparativecomposition (%) of decantedrose oils of

Turkish origin produced in differentfactories over two seasons

lslamkiiy Giineykent Kilic Yakaciren lslamkoy G0neykent Kilic Yakaoren

Compound 1990 1990 1990 1991 1 9 9 1 Compound 1990 1990 1990 1991 1991

acelone t t linalool 0.31 0.19 0.27 1. 7 4 0 .2 1

ethyl acetate t 0.49 t o,-guaiene 2.92 2.25 2.76 0.58 2.78
ethanol 0. 11 0. 14 5. 04 0.07 terpinen-4-ol 0.11 0.06 0.08 0.31 0 .1 0
pentanal I I t 0. 15 t hexadecane 0.14 0.16 0.12 0.05 0 .0 5
2-butanol I 0.06 t citronellyl
formate ttttt
a-pinene 2.20 1. 44 1. 42 0. 18 1" 33 citronellylacetate 0.82 0.69 0.81 0.18 t
isobutanol t t t 0. 14 t cr-humulene 1.51 1.17 0.98 0.39 0 .8 4
B-pinene 0.52 0. 35 0.35 I 0.31 neral 0.26 0.26 0.37 0.69 0.42
sabinene 0. 15 0. 12 0. 15 I 0.12 o,-terpineol ttt0.430.06
butanol t T-muurolene 2.07 1.93 2.11 0.44 3 .0 0
2-propenol- t 6-guaiene 1.23 0.99 1.16 0.20 1 .1 2
myrcene 0. 85 0. 61 0.62 0 .0 6 o.at heptadecane 1.92 2.30 1.62 0.94 2 .1 7
d
u
-+a! vr, nih6h6
H" 'v ' 'v
0. 06 t I t I geranial 0.43 0.37 0.60 1.06 0.48
heptanal 0.07 i 0.06 0 .16 0.05 heptadecene* 0.43 0.49 0.40 0j2 0 .1 6
2-methylbutanol 0.05 0.06 0 " 0 6 0 .6 1 I geranylacetate 2.25 2.27 2.10 0.65 2 .1 1
1,8-cine ole 0.09 t -I citronellol 35.18 24.47 28.57 38.78 26.47
2-hexenal* tt t tt nerol 2.76 3.19 7. 5 7 7.20 3 .6 9
2-amylfuran I- octadecane 0.27 0.18 0.29 1.06
(Z)-B-ocimene tt 1 tt 2-phenethyl
acetate 0.35 0.38 0.42 0.34 0.49
pentanol+ y-terpinene 0. 15 0. 09 0 .0 8 0 .1 4 0.07 geraniol 4"09 6.04 13.65 13.18 6 .3 9
(E)-B-ocimene 0. 07 0. 05 I tt 2-phenethyl
alcohol 0.50 0.33 0.63 0.99 0.70
p-cymene tt I -t nonaoecane 15.19 18.95 13.80 6.44 1 8 .0 2
terpinolene IT I tt 1-nonadecene 4.21 5.40 3.56 1.80 3 .8 0
(E)-3-hexenol -t I methyleugenol 0.93 0.61 0.60 3.26 1 .0 8
6-methyl-5-hepten- etcosane 1.54 1.91 1.36 0.57 1 .8 3
2-one - 0 .0 5 t /F\- O- a i n n co n o 0.37 0.31 0.24 0.11 0 .3 7
cls-roseoxide 0. 36 0. 18 0 .1 9 0 .7 3 0.17 (Z)-nerolidol 0.11 0.23 0-07 0.o7
frans-roseoxide 0. 13 0. 07 0 .0 8 0 .1 3 0.07 heneicosane 5.BB 7.69 4.92 2.28 6.50
(Z)-3-hexenol - 0.08 /F\- 4 - a i n n ca n a 0.19 0.38 0.17 0.07 0 .1 8
nonanal 0. 13 0. 09 3
-0 .1 0 .0 7 0.14 eugenol 0.25 0.35 0.37 0.68 0.36
6-methyl-5-hepten-2-ol t docosane 0.10 0.30 0.05 0.06 0 .0 5
++ tricosane 1-23
citronellal 1.26 1.68 0.87 0.40
nontrdonane -;
0.67 t
\it
0.60 0.23 0.80 /F F\-farnaenl 0.47 1.33 0.80 0.29 0 .8 1
benzaldehyde
. correctisomernot identified
t = t r a c e( < 0 . 0 1 % )
 Table Vlll. Comparative composition (o/o)of some blended rose oils of
Turkish origin produced in different factories over two seasons

1990 1991
Compound lslamkoy Giineykent Kilic Yakaoren Private lslamkriy Gtineykent Kilic Yaka<iren Private
acetone I I -I t t
6 lh\/. ^at at 6 t t t o.12 0.12 tt 0.16 I 0.17
ethanol t 0.25 13.43 3.70 2.67 0.14 0.16 4.02 0.20 2.96
pentanal I I 0 .1 6 t 0.08 tt 0.14 t 0.07
2-butanol I I t t t I- 0.06 I
(x-prnene 1 .1 2 1 .7 5 0 .5 4 0.81 0.60 0.08 0.63 0.26 o.72 0.35
isobutanol 0 .0 6 t 0 .16 o.o7 0.06 I- 0.13 t t
p-pinene 0 .2 9 0.42 0 .13 0.20 0.14 t 0.13 0.06 0.1I 0.10
s ab t n e n e t 0.06 t t 0.06 t I
butanol :ou :on t t t t :ou I
2-propenol* t t t 1 I
myrcene 0.48 0 .6 9 0 .2 0 0.38 0.30 0.07 o.26 0.08 o.25 0.19
d-lerpinene I 0 .0 5 t t I t t I t t
heptanal 0 .0 5 0 .0 6 0 .16 0.11 0.12 0.05 I 0.15 0.14 0.13
2-methylbutanol t 0 .7 6 0.40 0.34 0.07 0.08 0.55 0.08 0.50
1, 8 - c i n e o l e t : t
2-hexenal. t
l t
I
t l t
t
t
t
I
t
I
2-amylfuran t t t I
(Z)-B-ocimene I I t t t I t t
pentanol+ y-terpinene 0 .15 0 .1 4 o .1 4 0.12 0.16 I I 0 . 13 o.o7 0.12
(E)-B-ocimene 0 .0 5 0 .0 6 I t I I I I t
p-cymene t I I I I I t I t
terpinolene t t t t t
(E)-3-hexenol t
I I

t t l l
6-methyl-5-hepten-2-one 0 .0 6 tI t t t I I
cls-roseoxide 0 .3 1 0 .3 2 0.77 0.55 0.74 0.33 0.51 0.67 0.42 0.86
frans-roseoxide 0 .1 2 o _ J2 0 .2 0 0.1s 0.21 0.11 0.18 0.13 0.13 0.27
(Z)-3-hexenol I 0 .0 5 tt 0.07 t 0"05
benzylmethylether I l I
t
nonanal 0 .1 2 0 .1 1 0 .o 7 0.09 0.08 I I 0.08 0.14 0.07
6-methyl-5-hepten-2-ol tt t tt
citronellal t t tt I ; I.
pentadecane 0 .8 8 0 .9 2 o.tu 0.43 0.32 0.39 0.39 t o.73 0.46
benzaldehyde o .' t7 0.07 0.08 0.20 - 0.13
linalool o .2 0 0 .3 0 0 .1 6 0.69 0.97 1.28 0.85 1.56 0.66 1.26
a-guaiene 2 .9 0 2 .3 0 0.87 2.21 0.96 0.61 0.71 t 1.93 0.90
terpinen-4-ol 0 .0 8 o .o 7 0 .2 5 0.23 0.30 0.38 0.32 0.27 0.21 0.35
hexadecane 0 .1 7 0 .1 6 0 .0 7 - 0.06 0.09 0.07 o.o7 0.11 0.11
citronellylformate I I t I I I t 0.12
citronellylacetate t 0 .6 7 0 "3 0 0.63 0.29 0.61 0.25 0.24 0.59 0.35
o-h u m u l e n e 1.1 6 1 .2 0 0 .5 3 0.89 0.69 I t 0.47 0.88 0.46
neral 0 .2 4 0 .2 5 0 .6 0 o.42 0.56 0.44 0.59 0.64 0.40 0.43
c-terpineol 0 .0 5 t 0 .2 4 0.14 0.21 t 0.19 0.38 0.13 0.35
2 .3 6 ' 1 .8 8 0 .6 6 1.76 0.76 t 0.60 0.64 2.20 0.63
Y-muurolene
6-guaiene 1 .2 6 0 .9 4 0.38 o.o7 0.41 0.29 0.25 0.29 0.77 0.34
h a n t.d 6^.^6
2 .3 0 2 .3 6 | -JC 1.28 1.27 0.44 1.80 1.28 2.05 2.59
geranial 0 .4 9 0.43 0 .8 9 0.65 0.92 0.33 0.75 0.98 0.54 0.65
h a n t.d 6.6h6*
0 .3 2 0 .4 3 0 .1 7 0.27 0.15 0.31 0.21 0.16 0.23 0.29
geranylacetate 1 .2 0 I.J J 0 .3 8 1.36 0.88 1.97 1.19 0.68 0.80 0.36
citronellol 31.77 33.44 4 1 .8 6 41.56 42.97 26.45 36.54 36.89 39.0-9 38.63
nerol 0 .7 5 2 .2 9 3.28 3.79 6.13 7.06 |. to 6.30 3.72 3.19
oclaoecane 0 .1 9 0 .2 6 0 .1 2 0.17 0.22 0.98 0.95 t.Jc - 1.14
2-phenethylacetale 0.38 0 .4 0 0 .6 0 0.51 0.78 0.59 0.59 0.61 0.74 0.52
geranrol 2 .' t1 3 .8 3 5 .5 7 6.20 11.58 18.04 15.37 12.74 7.09 6.85
2-phenethylalcohol 0 .5 3 0 .5 8 0.75 0.67 1.17 1.83 2.15 1.30 1.05 1.25
nonadecane 2 0 .6 0 1 8 .3 4 1 0 .11 11.36 8.28 10.55 9.31 14.50 14.98
1-nonadecene 6 .0 0 5 .0 8 3.13 2.54 4.01 3.01 2.82 3.73 4.12
methyleugenol 0 .7 7 0 .8 1 1 .9 0 1.66 2.50 t.Jo 2.38 2.10 2.35
eicosane 2 .2 4 1 .8 1 1 .8 4 1.22 0.72 't.04 0.86 0.89 1.31 1.04
/tr\-o-oinncona 0 .3 5 0 .3 0 0 .1 1 0.23 0.14 U .J I 0.14 0.20 0.20 0.15
(Z)-nerolidol 0.42 0 .1 2 t 0.09 t 0.34 t 0.15 0.17 r
heneicosane 8 .9 0 3 .0 3 4.58 2.87 2.91 3.65 2.93 4.88 4,17
(E)-5-eicosene o .2 8 0.25 0 .1 3 0.15 0.10 0.27 0.13 0.10 0.16 0.16
eug e n o l 0 .2 8 0 .2 8 0 .3 0 0.30 0.49 0.88 0.55 0.62 0.70 0.38
oocosane 0 .1 3 0 .0 7 0 .0 5 0.08 0.06 0.15 0.08 0.06 0.07 0.10
tricosane 1 .9 1 1 .5 4 0 .5 1 0.87 0.54 0.29 0.79 0.51 0.84 0.78
(E,E){arnesol 0 .5 6 0 .6 7 0 .2 3 0.43 0.41 0.99 0.61 0.35 0.43 0.33
* correctisomernot identified:t = trace (< 0.01%)
 Table lX. Comparativechemicalcomposition (%) of four rose oils produced in different locations

Kushui Pingyan Kushui Pingyan

(Gansu (Shandong (Gansu (Shandong
Compound France Morocco provice) province) Compound France Morocco province) province)

pentanal - 0 -0 .1 bourbonene* 0.07 0.08

3-methylbutanol 0. 11 - 0.02 cr-cedrene 0.05
pentanol - 0 .0 1 -0 .0 2 - B-elemene 0.10 0.09 0.05
hexanal 0. 02 - 0-0.02 2-dodecanone - 0.04-0.05
3-hexenylformate. 0.02 - 0 .0 1 -0 .0 7 0.01 methyleugenol 1.49 1.24 2.30-2.38 2 .3 8
hexanol 0_.24 0.05 0.09-0.24 0.07 B-caryophyllene 0.76 0.42
2-heptanone - 0 -0 .1 4 a-guaiene 0.42 0.44
3-methyl-2-hexanol - 0-0.05 B-cubebene - 0.03-0.04 0.",
3-heptanol 004 c{,-bergamotene - 0.08 0 .0 6
heptanal o.oa o.o2 0.22-0.30 geranylacetone 0.11 0.08
c{,-pinene o .4 7 0 .3 1 0 .1 1 -0 .1 3 0.01 (Z)-B{arnesene 0.38 1.05 0-0.90
benzaldehyde - 0.06-0.1 0 0.02 cr-humulene 0.24 0.23
:oo
6-methyl-5-hepten-2-one - 0-0.02 0.01 allo-aromadendrene - 0 .1 4 1. 7 8 - 2 . 8 1
0.06 0-0.03 B-maaliene 0.13
B-pinene
myrcene 3.29 1.89 0.04-2.27 0.05 y-muurolene 0.09 - 0-0.61
octanal 0. 06 - 0 -0 .0 1 B-bergamotene- 0.18
a- phellandrene 0. 16 0.07 0.02-0.07 pentadecane 0.46 o.uo -
o-terpinene 0.24 0 .10 0 -0 .0 8 ar-curcumene - 0.06 0.06
p-cymene 0.09 0 .0 7 0 .0 1 -0 .0 3 0.04 2-tridecanone 0.94 3.07-3.84 0.49
lrmonene 1. 91 1.0 5 0 .0 1 -0 .8 8 0.04 2-phenethylvalerate - 0.08
(Z)-B-ocimene 1. 20 0 .7 4 0 .8 8 -1 .1 3 s{arnesene* 1.15 0.28-1.1 1
(E)-B-ocimene 1. 74 1 .1 1 0 .0 4 -1 .4 3 0.02 B-selinene :un 0.09
6-2-carene 0. 1B ou 0.02-0.04 2tridecanol 0.29
1,4-cineole : 0.., Y-Caornene 0.07 0.09 0.06
cis-linalooloxide 6-cadinene o.17 0.17 0-0.05
(furanoid) 0. 18 0.02 0.02-0.08 0.06 B-bisabolene 0.04
frans-linalool oxide nerolidol. 0.06 0.20 0.07-0.14 0.04
(furanoid) 0-74 0.34 0-0.34 0.05 g-muurotene 0.05
linalool 2. 91 1. 19 . 78
1. 23- 1 5.56 elemicin - o.oo 0"02
cls-roseoxide 0. 41 0. 44 0. 19- 0. 20 0.21 dodecanoic acid 0.03
/rans-roseoxide 0. 14 0. 14 0. 07 0.10 2-phenethyl-3-methyl
2-phenethyl alcohol 2.36 0.79 - 0.30 valerate 0.03 0.05
an allo-ocimene* hexadecane 0.07 0.16
citronellal :o' - 0-0.05 2,3,4,5{etramethoxy-
benzyl acetate - 0.03-0.08 - allylbenzene - 0-0.12
ethyl benzoate o .1 2 0.04 2-tetradecaone - 0.06-0.18
pinocarveol* 0.03 hexadecanol 0.02 0.04
terpinen-4-ol o.t, 0. 11 guaiol 0.03
tr{erpineol o_72 0. 18- 0. 50 u.o+ 2-phenethylbenzoate0.02 0.01
campnor 0.29 heptadecane 0.16 0.31
menthol 1.00 I-h6nla.lo.ana 1 I6 2.34 0-0.16
methylsalicylate o-27 0.38 2-petadecene. - 0.54-0.79
citronellol 4 1 .0 1 40.00 55.13-55.57 64.22 farnesol* o.oa 0.18 0.23-0.7 3
isogeraniol 0 .1 9 0. 11 0. 09- 0. 11 benzylbenzoate 0.05 0.10 I
0.13-0.1
geraniol 3.82 2.44 4.88-9.40 13.74 1-octadecene 0.03
hexylcrotonoate 0.04 octadecane o-17 o.22
citronellylformate 0.48 0.33 0.06-0.20 2-phenethyl
2-undecanone 0 .0 1 0 .1 5 -0 .1 8 0.03 phenylacetate 0.04 0.38
geranial - 0-0.35 farnesylacetate* 0.52 0.45 0.04-0.47
2-decanol :* 0.03 1-nonadecene 3.14 4,25
2-undecanol - 0.26-0.30 - nonaoecane 12.34 16.03 0.13-0.1 9
geranylformate 0.03 0"06 farnesylpropionate* 0 . 3 1 0.50
methylgeranate 0.24 0 .3 1 0 .0 6 farnesylbutyrate- - 0-0.27
citronellylacetate 0.25 0 .9 1 2 .6 4 -6 .0 3 1.18 1-eicosene 0.09 0.39
eugenol 1 .1 9 0.34 0.49 etcosane 1.01 1.49 0-0.09
"{.52-1.38 1-heneicosene 0.10
n ar \ / l r naiaia 0 .1 0
isogeranylacetate o .3 2 0 .1 9 heneicosane 4.40 5.82 1.15-1.22
geranylacetate 0.34 - 0.18-0.70 0.40 oocosane 0 . 10 0.13
\rr 1-tricosene 0.07 0.13
o-elemene - 0-0.44
decanoicacid 0.07 lncosane 0.76 1.47
* correctisomernot identified

130
 geraniol(26.70%) ercosane(1.45%)
Table X. Comparativechemical composition (%) citral-(0.s8%) heneicosane(6.34o/")
of some rose absolutes citronellylacetate(0..1
0%) C' Ho, alkene*(0.35%)
nerytacetate(0"19%) oocosane(0.26%)
R. Sutter's Crimson Starof Chrysler geranylacetate(1.86%) tricosane(2.94%)
Compound centifolia Gold Glory Holland lmperial heptadecane(0.80%) Cr.Houalkene*(0.85%)
C,rHroalkene"(0.15%) tetracosane(0.24%)
benzylalcohol 1.5 0 .3 2 .0 2. 0 1.0 octadecane(0.14%) pentacosane(1.21%)
linaalool+ 2-
farnesol*(0.25%) nexacosane(0.60%)
phenethylalcohol 78.1 3 2 .0 3 5 .0 43. 0 35.0 nonadecane (11.20o/") heptacosane(0.98%)
nerol+ neral+
C,nH.,alkene*(2.94y") CrrHu,alkene*(0.07%)
citronellol 9.2 1 0 .0 4.0 13.4
*
2-phenethyl correct isomer not identifieo
acetate 0.3 4.0 2 .0 1. 5 0.5
geraniot+ geranial 3.6 19.0 1 5 .0 14.0 17.0 Aiso in 1995, Etienne comparecl the composition
nerylacetate - of the
0.1 0.4 0. 5 0.1 absolute of R. centifolia with iab-prepared a6solute
citronellylacetate 0.2 0.1 0. 1 of four
0.1 rose cultivars (Setters Gold, CrimiorrGlory Star
geranylacetate of Hollancl
0.2 0.1 0 .5 0.1 and,Chrysler Imperial). The resuits of Etienne,s
eugenol 0"8 0.1 analyses
0 .2 0.2 can be seen in Table X.
cl-copaene+ methyl
eugenol 0 .5 0 .5 0 .3 0.4 K. Takahasiii, S, Muraki and T. yoshida Sqnthesisand
, distribution
B-caryophyllene 0 .2 0 .3 0 .3 of (-)-mint suphtde,
guaiadiene. .a 21yel yfur- cint aining sesq tnt ery ene.
0 .1 0 .5 0 .1 Agric. Biol. Chem., 48, Izg_] .ilitOSt).
o-terpineol - 0 .8
germacreneD B L_:y-.:lce, Progressin essentiol oils. perfum. Flavor., 16(3),
0 .2 0 .1 0 .1 Y:
43-77 (1991).
farnesol* 0 .6 2 .2 0 .5 D-! Xup, Z-L. L1, y-2, Chen andZ_2. Shi, Cornttarison
pentadecane 0 .1 beta^een
0 .1 0 .1 the chemical a.tmponent,sof e_ssentialoilsuf thn
nonaoecene* 0.8 12.0 f.n grr;run
1 0 .0 in China. Tranran Chanwayanjiu yu Kaiia, f (it, 3O_+t
nonaoecane -ri ( 19g9).
z .c o .U 3 .0 K. H. C. Baser,Turkishroseoil.perfum. Flavor.,l7(3),18-52(Igg2).
etcosane 0.2 0.3 0 .2 E-J. Brunke. F-J. Hammerschmidt and G. Schmaus,Tlrclrcacl,space
heneicosane 0.5 1 .0 1 .0 onatutrsoJJtouer Jrograncas.Dragoco Rept., (I), 3_31(lgg2).
correctrsomernot identified E-J. Brunke, F-j-. Hanrn-rerschmidtand G. Schmtrus,Scent
of roses
-recent results.FIav. Fragr.
J., 7, f95_1gg(1992).
R. P. Sood,B. Singhard\'. Sin gh,Constituentsof roseoilfrornKnngra
VII and VIII shor,vthe results of this study.As can be seen, Yalley,H. r. Qnclia). Esient. Oil. Res.,4",425_42b(1992).
].
some of the constituentsvaried quite widely from factory to P. Kreis and A. Mosan dl, Chiral contprxtnclsof esserftial
oils. patt
factory but there wasalsoa constituentvariancefrom season Xll. Aulhenlicity re111ypl o.f r,,.s',,
,,il rtsing ennnlioselcctiL.e
to season.The authors recommended that extensive re_ nrullit.litnensiotral
gas chrt)mofr,ordplty. Flav.Fragr.J.. 7. lgg_
203 (1992)
search be done on rose oil production in Turkey so that
U. E Putievsly, I. Katzir, R. Ikan arrd V. Weinstein,
Turkish rose oii can becorne a more wiclely accepted fra_ ,Ravid.
uctcnntn(ltion oJ
grance material with a more standardizedcomposiiion.The _tlrcenantiomeric composition of citronellal in,
es,senlial yil.sby rltiral CC nnnly.si;rttt ri ttldifierl \_rA,lnl,d,,ritrli,
reviewer hopes that this recommendation is supported by
lthnse.Flat. Fraqr.J. 7.235_238( 1992).
the rose oil producers in Turkey because,once the work ha.s X-Y. Ma, H-P. Pan, F-X. Zhao, H_e. Li and.X_Z.Chen,
Chemical
been done and appropriate processingchangeshave been constituents in es,sentiuloils nt tra nsllo tfted ,osesoj European
frtt
madeto standardizethe oil. a[ partiesblnefit.ihe enclresult o r i g l n , F e n r i C l r e s h i X u e b u ol.2 r 5 r . i _ O
rtggft.
could be an increased_ need lor rose oil by the fragrance H M.,Guentert and H. Harder, Volatile cornT:ounds
furbure, frorn
Who knows, the price of the oil de"crease Jlouers Anolyticol ancl ofoctory aspects.In: Bioactiue uilatile
fdyiT. compound^s
slightly becauseof increasedI,relds. -"y ",r", frornplants.-Fdits., R, feranishi, R. G, Buttery ancl
H. Sugisawa.p?..168-186,ACS SyrnposiumSeries525,
Also in 7941, Yr et al. used GC/MS to compare the Amer.
L n e m . s o c . . \ \ a s h i n g t o n( 1 9 9 3 ) .
composition of rose oil obtained from France ancli4orocco
L-F.Zln,Y-H. Li, B-L. Li, B-y. Lu and N-H. Xan,Aromatic
with oils produced in two different regions of China. The plants
and essential constihrcnts. South China Institute of B'otany,
results of this study can be seen in Tabie IX. ChineseAcademyofsciences,Hai Feng publish.Co.,dlstrlbuted
In 1995, Gora et al. examined an oil produced by bv PeaceBook Co., Ltd., Hong fong
if SO,:).
hydrodistillation of R. centfoliapetals, usifi a combination A. Bayrak,and A. Akgiii. Volatile oil cornposition of TtLrkish
rose
of GC (retention indices) and CbZnrlS.T4r"v fo,rnd that the (Rosl domaceria). Sci. Food Agric., A+, S+t_+4A
J. egg+).
oil contained: Z. Yu, Y-F. Yi, Y. Wu, X-J. yu, p. Want and
J_K. Ding, The
\ll comparison of the chemical constituent,sand tite urdn,irf
myrcene(0.08%) menthol(0.07%) rLtseoils.Acta Botan. yunnanica, f6(1), 75_g0(i994). .fur,,
linalool(0.10%) 2-phenethyl alcohot(0.60%)
c/s-roseoxide (0.14%) J. Gora, A. Lis and D. Kalemba, Chemical composition of tlrc
citronellol
(22.9%) e,s1eyl g]-gll of Rosa cent
trans-roseoxide (0.07%) nerol(14.26%) foli a L. 7.tetals. J. tr ssent. Oii Res.. i, S9_
90 (1995)

131
J. J. Etienne, QtLatre roses rtrxrcelles pour des accords inddits. camphor(8.6-14.0%) cterpineol(1.2-1.6%)
Parfum.Cosmet.Arorn..No. 126.38-44(1995). bornylacetate(0.7-1.1%) borneol(3-2-4.0%)
e (1.4-2.1
B-caryophyllen %) caryophylleneoxide(1.2-1.B%)
YarrowOil (4.6-6.8%)
tepinen-4-ol chamazulene (1.5-2.2%)

Using their olrm version of a retention index systemon two

packed columns of differing polarity, Lemberkovics and
T\r'o years later, Figueiredo et al. (1992) compared the
Verzar-Petri( 1985)tentativelyidentified a fewsesquiterpenoid
comoositionof the oils obtainedfrom the flower headsof two
compoundsin Hungarian yarrou' oil. The compoundsdeter-
pop.tlutiotr. of A. mittefolhtm ssp.millefolium. They com-
mined to be present in the oil were:
pared the composition of'oils obtained {rom closed flower
B-caryophyllene heads, young flower heads, fullv open flou'er heads and
cr-humulene cnamazulene flower heads that had dried on the plant. The oils were
T-muurorene caryophyllenol-l
isolatedby use of a Likens-Nickersonsimultaneousdistilla-
Three vears later, Lemberkovics et al. (1988) reported tion and extraction (SDtr) and by hydrodistillation using ir
th:rt a sample of Hungarian yarrow oil contained: Clevenger-t1pesystern.The oils produced by SDE were
(4.1%) lavandulyl acerare(4.4k)
used for analysisby GC and GC/MS, and the results of the
cr-pinene
B-pinene(20.8%) bornylacetate(0.8%) analysesare presented in Table XI. The oils produced by
limo ne ne(1 .6% ) B-caryophyllene (11.9%) h1'drodistillationu'ere used to estimateoil yield.
1,8-cine ole(1.7 % ) cr-humulene (2.5%) Tlie sameauthors (Figueiredo et al. 1992)trlsocompared
borneol(0.3%) T-muurolene (7.4%)
the composition of oils produced frorn the flor,versof A.
o,-terpineol(0.3%) y-cadinene (1.0%)
(0.2%) caryophyllenol-l(2.2%)
ntillefoliurn ssp. rLillefoliurn with oils produced from the
citronellol
linalylacetate(1.3%) chamazulene (12.5%) leavesof the sameplants han'estedr,vhenthe plants were in
the vegetative stageandrvlien thevu'ere in full flou'er. Again,
In 1990, Kreis et al. used enantiomeric separationon a the oils for analysisrvere isolated by SDtr and analyzedby
chir:rl ctroillarv GC column to determine that the enantio- both GC and GC/MS. The resultsof this studv are shown in
meric raiios oi a-pinene, B-pinene and limonene in valrorv Table XII. As can be seen, the oil produced from leaves
oil were: harvestedfrom plantsin full flowerhad a similar composition
(59%)
e (41%): (R)-(+)-cr-pinene
(S)-(-)-o-pinen to the flower oil. In contrast, the oil produced from leaves
(S)-(-)-0-pinen (18%)
e (82'k): (R)-(+)-B-pinene harvested frorl plants in the vegetative stager,vasvery differ-
e (23%): (R)-(+)-l
(S)-(-)-limonen imonene (77"k) ent, being rich in germacrene D and other sesquitetpene
This san-reyeaq Kedzia et al. (1990) reported that yarror'v hydrocarbons.
oil of Poiish origin contained the {bllowing composition: This samevear,Hofmann et al. (1992) carried out a more
detailed analysison yarrow oils produced from different
cr-pinene(0.06%) ctterpineol(1.4%)
bornylacetate(0.9%)
plant collections.As part ofthis study,the authors determined
camphene(1.5%)
lene (8.2%) that the oils (samplesl-3) rvere produced {rom plants th:rt
B-pinene(3.0%) B-caryophyl
1,8-cineole(3.4%) o- hum ulene( 1. 2% ) possesseddifferent levels of ploidy. For example, the
camp ho r(1 .3% ) caryophyllene oxide(7.8%) chromosome numbers of samples 1-3 were 2n=36, 2n=72
borneol(2.5%) chamazulene (13.0%)
:rnd 2n=54, respectivelrvThe results of the analyses(CC
Furthermore, the authorsdetermined that the oil showed and GC/MS) of oils from thesethree samplescan be seenin
a strong activity againstStaphylttcoccu,s aureusandCandida Table XIII.
albicons.This activitv was further determined to be related AIsoin 1992,Belangeret al. comparedthe compositionof
to the chamazulenecontent. oils produced from A. m.illefoliuniharvested at an experi-
Also in 1990, Hachey et al. reported the results of the mental farm in Quebec. Using GC retention indices on tr,vo
analvsisof the oils obtained from a number of collectionsof capillary columns of dissimilar polarity, the authors com-
l,chittea tnillefoltum that r'vere har-vestedfiorn wild plants pared the oils obtained from rvhole plants (fresh and dried)
grorvingat diff'erentsitesin the Snguenayregion in Quebec flor,vers and leaves with the headspace from fresh u'hole
(Canada). The analyses,which rvere performed on lab- plants. Their analytical data can be found in Table XI\{
prepared oils, used a combination of GC and GC/MS. The Based on the data obtained by Figueiredo et :rl. (1992)
cornpoundsidentified and their range of quantitative vari- (cf. TableXII), it is surprisingthatthe germacreneD content
ance are summarized as follorvs: of the flower oil u,ashlgher than the leaf oil.
&. Chatzopoulouet al. (1992)performed an an:rlysisof an oil
(1.1-1.9%)
o.-pinene lim onene( 0. 4- 1. 9% )
1,B-cine*ole(7.7- 19.5o/o) oI A. millefoltu.nn collecred from the Chalkidiki peninsula
camphene(1.2-2.574
y-terpinene (1.6-3.0%) near Thessaloniki(Greece) using GC and GC/MS. They
B-pinene(3.8-B.B%)
sabinene(5.7-10.07%) p-cymeHe(1.6-2.3%) ibund that the oil possesseda cornpositionthat heretofore
myrcene(2.8-10.0%) terpinolene (0.3-1.9%) had not been encountered in the A. nillefollam complex.
o-phellandrene (t) othujone (0.5-1A%) The componentsidentified in the oil rvere:
cr{erpinene(0.7-1.0%) B-thujone(8.3-24.7%)
 Table Xl. Comparative chemical composition (%) of oils produced from flower heads
ot Achillea milletolium ssp. millefolium at different stages of maturity

Compound 1A 1B 1C 1D 2A 28 2C 2D
tricyclene I I 0.1 0.2 I
o-thujene 0 .2 o .2 o.4 0.6 0.2 0.2 0.2 I
CI-prnene 2 .6 2 .5 3.8 2.1 5.5 4.7 4.2
campnene 0.6 0 .6 0.6 0.5 2.2 2.O 2.5 1 .9
sabinene 24.7 28.6 30.5 18.9 3.5 3.7 2.9 1-2
B-pinene 2 .5 1.2 2.3 2.0 11.4 9.9 9.5 o.I
myrcene 1.0 0.8 0.5 I
o-phellandrene I I 0.1 o.4 0.9 0.4 0.5 0. 4
cx-terpinene 1.1 't.2 I.3 2.2 0.7 0.5 0.6 0. 6
p-cymene 0 .6 0 .7 0 .9 2.1 0.3 0.3 0.6 o. 7
1,8-cineole 20.5 23.8 24.7 AAF
14.7 15.8 17.4 1 8. 3
limonene 0 .7 0 .8 0 .8 1.1 0.5 0.5 0.5 0. 6
y{erpinene 2 .5 2 .5 2 .8 3.5 0.5 0.5 0.6 0. 5
trans-sabinene hydrate 4 .0 2 .4 t.o 1.4 0.5 0.4 0.2 o. 4
terpinolene 0 .4 0 .4 0 .5 0.8 0.2 0"2 0.2 I
crs-sabinene hydrate 1 .2 0 .7 0 .7 1.0
frans-p-menth-2-en- 1-ol 0 .6 0 .3 0 .3 0.2 J. / J.J 3. 3
campnor 2 .3 2 .0 1.7 1.2 21.87 zJ.z 25.5 30.8
frans-pinocarveol 0 .2 o.2 0.3 o.4
cls-p-menth-2-en- 1-ol )u z-z 2.5
prnocarvone u .b 0 .6 o.7 o.7 0.4 0.3 0.4 0.7
b-terpineol 0.8 0 .9 0.9 1.0
oorneol t.c 1.6 2.3 J-O
lavandulol 0.6 1.1 2.0 1. 3
terpinen-4-ol a.t io i, 3.4 0.7 0.9 1.1 1. 2
myrtenal t 0 .3 0.3 o.4 0.4 0.5 0.8 1.1
i cr-terpineol 2. 6 2.2 1 .7 0.9 1.1 1.2 0.9 0. 7
myrtenol I 0 .5 o.7 1.1 0.9 1.0 1.0 t.c
trans-carveol 0 .7 0 .3 0 .3 0.1 0.7 0.7 0.5 0. 8
c/s-carveol t 0 .2 0 .2 0.5 I 0.1 0.1 0.2
(Z)-ocimenone t 0.1 0.2 I
c/.s-chrysanthenylacetate 2 .O o .7 1.1 1.2 0.3 0.2 0.2 0. 3
bornylacetate 1 .0 1 .8 1.5 1.8 0.7 0.6 0.6 0. 8
nerylacetate I t.o 1.7 0.5 2.6 2.9 2.9 0. 6
trans-cawylacetate 0.8 0.7 0.7 0. 6
eugenol t o.u 0.4 v,1 t 0.6 0.4 0"2
6-elemene t t 0.1 1
cls-carvylacetate t T t t
c/s-jasmone 2.0 1.9 1.9 1
B-elemene 3 .2 1 .7 1.0 I I I T I
B-caryophyllene 1 .2 0 .5 0.5 t 0.7 0.6 0.3 t
c{-humulene 0.2 I I I
germacrene D 6 .9 4 .5 3 .1 1.2 2,9 2.4 1.2 0. 8
bicyclogermacrene 1 .1 0 .5 0.5 I 1.3 0.7 0.3 t
cl-muurolene 0.2 0.2 t I I I I u.o
a-farnesene" 0 .2 0 .1 0.1 I
rcaornene I 0.1 I I
&cadinene I 0 .2 o.2 t 0.6 0.4 0.2 I
elemol t 0.1 I t
caryophylleneoxide 0.6 0.5 0.5 0. 5
T-cadinol rg 0.5 0.4 0.4 I
a-muurolol I 0.3 I I
(E)-nerolidol ^,:
ato 0 .9 o.u o.a
a-cadinol r, 1 ' 4 1.1 t.5 0.8 0.3 o.4 0 .5
chamazulene : 0.9 0.5 0.3 0 .1
- correctisomernot identified;t = trace (< 0.1%)
Lege n d l:a n d 2 r e l a t e t o d iffe r e n tlo ca tio n so fcu ltiva tio
A=n ;clo sedfl ow erheads;B =youngfl ow erheads;C =ful l yopenfl ow erheads;D =dri edfl owerheads
 artemisiatriene (0.4%) isoborneol (2"0%)
tricyclene(t) terpinen-4-o ( 1l . 1 % )
Table Xll. Comparativechemical composition (o/o)
d,-thujene(t) o-terpineol(0.5ol.)
of the flower and leaf oils of
s-pinene(0.4%) verbenone(0.2%)
Achillea millefolium ssp. millefolium
camphene(0.9%) ascaridole*(47.2%)
1-octen-3-ol (t) thujylisobutyrate (1.4%)
Compound Flower oil Leaf oil A Leaf oil B sabinene(0.4%) geranial(0.3%)
t B-pinene(0.3%) chrysanthenylacetate"(t)
tricyclene
myrcene(t) ascaridole- (2.1%)
cx,thujene o .4 t 0.2
o-phellandrene (t) carvacrol(t)
o(-pinene l.Cl 0 .8 t h y m o l( 0 . 1 %)
6-3-carene(t)
camphene 0 .5 0 .4 o-terpinene(7.0olo) cls-jasmone(0.8%)
15.4 5.4 1.0 p-cymene(7.4%) cx,-copaene (t)
sabinene
1,8-cineole (10.5%) B-cubebene (0.1%)
B-pinene 1. 3 1. 1 0.3
l i m o n e n e( 0 . 1 %) B-elemene (t)
o,-phellandrene 0. 5 t
artemisiakeione(t) B-carophyllene (0.4%)
cx,-terpinene 2. 0 1. 1 0.3 yomogialcohol(1.7%) (E)-B{arnesene (t)
p-cymene z.z 2 .8 I y-terpinene(0.3%) cx-humulene (t)
28.7 24.5 o.4 trans-sabinene hydrate(0.4%) ar-curcumene (t)
1,8-cineole
artemisiaalcohol(0.5%) germacreneD (t)
limonene 0 .9 0 .8
terpinolene (0.3%) cx-muurolene (t)
y-terpinene c.1 |.at
linalool(0.5%) y-cadinene(t)
frans-sabinenehydrate 2 .1 10.2 cr-thujone (1.5%) 6-cadinene (t)
cr,p-dimethylstyrene 0 .1 B-thujone (0.2%) (E)-nerolidol (t)
terpinolene 0 .9 0 .5 cls-sabinenehydrate(0.5%) caryophyllene oxide(0.2%)
4 .6 camphor(8.1%) T-cadinol(0.1%)
cls-sabinenehydrate 1 .7
lavandulol (0.1olo) cr-cadinol (0.1%)
frans-p-menth-2-en-1-ol 0 .3 0 .7 cls-chrysanthenol (0.2%) cr-bisabolol (0.1%)
campnor 3 .3 4 .9 * only one isomer of ascaridolecan exist
trans-pinocarveol 0 .7 t = tr ac e ( < 0.1% )
pinocarvone 1 .0 1 .1
In 1993, Belanger and Dextraze analyzedoils produced
terpinen-4-ol 3.4 5. 6 from 68 different A. millefoliunr plants grown in Quebec.
myrtenal 0 .6 0. 6 0.3
Thev {bund that the ouantitativevariation in oil constituents
o-terpineol t.3 1. 2
was as follows:
myrtenol 1 .0 t.o
cr-pinene (0.10-1.70%) (0.04-5.50%)
y-terpinene
cuminaldehyde 0.5 1 .0 camphene(0-2.68%) crthujone(0-20.7'/.)
carvone 0.1 I-
sabinene (0.29-17 .20%) (0-35.1%)
B-thujone
acetate
cls-chrysanthenyl 2.5 0 .4 B-pinene(0.8-9.74%) camphor (0.20-6.70'/.)
cuminalcohol 0.4 myrcene(0.10- 14.7'/.) bornylacetate(0-3.88%)
cx-phel landrene(0-17 .4%) e (0.54-7.68%)
B-caryophyllen
bornylacetate 2 .3 4 .O (0.10-1.17'/")
o-terpinene (0-5.36%) cx-humulene
nerylacetate 1 .0 p-cymene(0-2.75%) germacreneD (6.21-54.7%)
eugenol o .2 1,8-cineole (0.26-6.45%) chamazulene (0.75-51 .3%)
+.o
l i m o n e n e( 0 - 3 . 11 %)
o-copaene 0.3 In 1995,trigueiredoet al. analyzedthecompositionof oils
B-bourbonene 0'2
produced from cell suspensioncultures of A. millefolium
0 .3 0 .6 0.5
ssp.millefoliurn. Although the yield of oils obtained {rom
B-caryophyllene z.'l
various cultures harvestedat 8-10 days(the end ofenviron-
germacrene D o .7 7.2 65.1 nrental growth phase) i,vasonly 0.0017o,the authors were
bicyclogermacrene U.J 0 .7 3.7 able to perform GC/MS analyseson them. Depending upon
g-muurolene - 0.2
the medium, the exposure to light and whether it was a
crjarnesene* - 12.0
single- or two-phasemedium, the oils produced the follow-
6-cadinene 0. 1 1.2 ing compounds:
T-muurolol 0.4
tricyclene(0-t) terpinolene (0-5.1%)
cr-cadinol 0.8
c-pinene(0-t) borneol(01)
* correctisomernot identified s a b i n e n e( 0 - 1. 1 %) methylthymol(0-1.0%)
Leaf oil A: Obtainedfrom leavesharuestedwh?n plantwas in full flowerstage o-terpinene(0-3.4%) eugenol(t-35.6%)
Leaf oil B: Obtainedfrom leaveshaNestedwhen plantwas in vegetativestage p-cymene(I-41.0%) B - e l e m e n (e0 - 1 0 . 1 % )
t = t r a c e( < 0 . 1 % ) 1,8-cineole (0-t) germacrene D (8.5-42.0%)
Irmonene (0-5.3%) demethoxyencecalin (0-11.3%)
T-terpinene (0-16.9%)
t = tr ac e ( < 0.1% )
 Tabfe Xlff. Comparative chemical composition (%) of the oils produced from three different Achillea mittefolium collections

Compound Sample1 Sample2 Sample3 Compound Sample1 Sample2 Sample3

butylformate 0.02 0.03 0.02 pinocarveol* 1.44 I I
a-pinene 1 .0 1 o .7 1 0.28 cls-verbenol 0.03 I o.o2
0-thujene 0 .2 1 0.03 0.07 5-terpineol t 0.38 I
(E)-2-butenol 0 .1 0 0 .1 3 0.08 Y-muurotene 0.06 t 0 .18
campnene 0 .0 1 0.25 o.o7 trans-verbenol 0.08 0.25
butylacetate 0.02 0.03 0.01 frans-piperitol I 0.03 i
hexanal t lavandulol 0.86 I
B-pinene 4.Oat 0 .8 6 4.84 germacreneD 7.13 1.57 2.87
sabinene 9.68 1 .0 1 5.21 borneol+ c{,-terpineol 0.91 15.44 o.+1
myrcene 0.42 0 .1 0 0.04 caryone 0.04 0.05 1
o(-terpinene 0.37 0.28 0.12 bicyclogermacrene 0.19 n i tr 0. 37
2-methylbutylisobutyrate+ p-mentha-1,5-dien-B-ol 0.14 0.05 0. 16
3-methylbutylisobutyrate 0 .0 5 I trans-carvylacetate 0.20
limonene 0. 19 0.30 0.22 6-cadinene 1 0.41 o.28
2-methylbutanol + cis-piperitol t 1 0.09
3-methyl-butanol t 0.12 c/s-carvylacetate 0.13
1,8-cineole 0.65 '11.69 0.46 cls-linalooloxide (pyranoid) 0. 13
2-pentylfuran t t 0.01 ar-curcumene ; u. t3 0.72
(Z)-B-ocimene 0.40 t 0.02 myrtenol 0.04 t 0.30
(Z)-anhydrolinalool oxide I (2E,4E)-decadienal 0. 01
T{erpinene 0.08 z- t5 0.63 calamenene- l 1
t
(E)-B-ocimene 0. 14 0.03 0.01 trans-caweol I 0.38 t
p-cymene 0.05 2 .9 8 0.38 p-cymen-B-ol t I I
2-methylbutyl2-methylbutyrate geraniol I I
+ 2-methylbutylisovalerate t I geranylacetone t 0.08
terpinolene 0.20 u. tc 0.13 benzylisovalerate
2-ethoxyethylacetate 0. 01 0.03 0.02 c/s-carveol :' u i*
isoamylisovalerate 0. 10 0.05 0.01 1,5-epoxysalvial-4(14)-ene I t o.oo
(E)-2-heptenal I trans-jasmone I
6-methyl-5-hepten-2-one t t 0.01 cls-jasmone 0.07 0.33 I
hexanol 0.03 0.03 0.02 B-ionone. I I I
(Z)-3-hexenol 0"05 0.01 '12-norcaryophyll-5-en-2-one t
nonanal t t 0.04 isocaryophyllene oxide t t 0 .0 9
3-octanol I caryophylleneoxide 0.51 1.04 2.52
B-thujone I salvial-4(14)-en-1 -one I 0 .1 0 0 .0 8
aceticacid t I o"o,1 humuleneepoxideI I
cls-linalooloxide (furanoid) 0 .15 humuleneepoxidell I 0.13 0.09
1-octen-3-ol 0.63 o.23 1,1O-epoxygermacrene D 0.02
frans-sabinene hydrate o.ou 0.33 0.62 (R)-caryophyll-5-en- 12-al I
lrans-linalooloxide (furanoid) 0.05 I (E)-nerolidol o.rt
cx,-copaene 0.05 0.18 epi-cubenol I o.ot
campnor 0.08 5.40 0.40 (S)-caryophyll-5-en-1 2-al 0.05
B-bourbonene 0. 19 0.05 0.08 p-cymen-7-ol 0.05
benaldehyde 0. 16 0.08 0.07 spathulenol 1 0.08 0.09
pinocamphone* 0.04 0.05 0.06 eugenol I 0.10 0 .0 1
B-cubebene t 0.30 0.10 T-cadinol t 0.03 0.02
cis-sabinenehydrate 0.20 0"23 0.40 cis-cr-cadinol 0.03 0.13
pinocarvone 0.57 I 0.06 0,-muurolol I 0.05 0 .0 3
linalool I 21.50 0.06 farnesal* 0 .1 8
1-nonen-3-ol 0.08 0.48 trans-cI-cadinol 0.10 0.46 0 .1 5
cls-p-menth-2-en-1 -ol o.o7 0.08 0.16 (E,E){arnesal 0 .1 4
B-carophyllene 14. 19 1 .1 7 3.13 decanoicacid I I
6-methyl-hepta-3,5-dien-2-one
;' 0.01 caryophylla-2(12),6(13)-dien-5-ol-- I 0.08
terpinen-4-ol 1. 12 1 .0 9 z- tJ caryophylla-2(12),6(13)-dien-5-ol-- 0.23 0.56
mynenal t -: 0.34 chamazulene 15.38 0.33
phenylacetaldehyde I (E,E)-larnesol 2.72
(Z)-B-farnesene \rr 0.03 dimethylvinylazulene. t
cr-humulene I 0.46 o.71
- correctisomernot identified;t = trace (< 0.01%)
 P. Kreis, U. I-Ienerand A. Nlosandl,Chirale inhaltstofl'cdtherischer
Table XlV. Chemicalcomposition (%) of Ole. III Stereodifferenzierung\.onct-Pinen,B-Pinenand Limoneri
Achillea milletolium oil and headspace in itherischen Olen, Dlogcn ind Fertigarznein'rittelrr.Deut.
Apoth. Ztg., I30,985-988 (1990).
Fresh Dried B. Kedzia, M. Krzvzaniak and tr. Holderna, Effect o.f L::Jarrorl)
Plant plant flower Leaf essentialoil (.Oleummilleftilii) and its rxtrrytrnrc:nts
ctnprfthogenic
Compound oil oil oil oil Headspace nicroorgonisms. Herba Pol., 36, 117-f25 (1990).
cx-pinene U.OJ 1. 66 t.oc 3. 10 5.54 J. M. Hachey, G. j. Collin, NI. J. Gagnon, S. Sirrrard,S. Dufour, F.
camphene 0.79 2. 20 t./o 5. 14 7.55 L Jean. G. Vernin and D. Fraisse, ExtrrLctionarLd,GC/trtS
sabinene 1 0 .2 0 8. 31 4.49 5.95 25.50 anahlsis o.f tl're essential oil o.f Achillea milleJoLiuntL. con'Lpler
2 .8 6 5. 69 4,49 13. 90 8.34 (Ctnnpositae). J. Essent.Oil. Rcs.,2, 317-326(1990).
B-pinene
A. C. Figueiredo,J. G. Barosso,M. S. S. PaisandJ. J. C. Sche{Tcr,
myrcene 3.35 6.00 3. 75 6. 30 11.20
17.70 Co nqto sition of tIrc essential oilsfrom to o p opukLtionso.fAchilLea
c-phellandrene 0.81 0. 36 -
millefoliunt L. s sp.mill eJoliurn. J. Chromatogr. Sci.,30, 392-295
n nO 0. 09 0. 19 0.39 2.28
^-+6rnin6n6
p-cymene 1. 05 0. 45 1.95
(1ee2).
0.66 0. 73
A. C. Figueiredo,J. G. Barosso,M. S. S. PaisandJ. J. C. Scheffer,
1,8-cineole 4.54 3.70 6.09 4.00
CompLtsition of the cssential oiLsfrcm leates ancl flowers of
limonene | .12 0.95 0"07 1. 25 2.20
Achillea nillefolium L. ssp.ntillefolium. Flav. Fragr. J., 7, 219-
Y-terprnene 0.83 1. 42 2-83 2. 30 1.77 222 (.1952).
cr-thujone 0"28 0. 40 1. 02 0. 50 1.80
L. Hofmann, D. Fritz, S. Nitz, H. KollmannsbergerandF.Drarvert,
B{hu jon e 1 . 60 3. 21 0. 59 0.25 12.10 Essential oil arnnpo.sitit'tr,'f tltrtc p,lyploicl.s in the Achillea
camphor 2.93 4.43 8. 01 16. 80 2.75 nillefolium cctmplex.Phltochemistry, 31, 537-512 (.1992).
bornylacetate 0.85 5.tz 2. 50 3. 02 1.48
A. Belanger,L. Dextraze,Y. Laclianceand S. Sirvard,ExtractiLn et
B-caryophyllene 3.96 2.84 2. 84 0.17
canrci drization cleI' achillde.ntillefeuille (Achillea millefolium L. )
cr-humulene 2.77 0.60 0. 11 0. 18 cultiode rru Qrrcbec.Rivista Ital. EPPOS, (Numero Speciale),
germacreneD 25.40 4.37 21. 60 10. 80 574-580(1992).
chamazulene 25.50 34.60 26.70 11. 10 P. Chatzopoulou, S. T. Katsiotis and A. Baerheirn Svendsen,An
ascariclolecontaining essentialoil of the Achillea ntillefolitLm L.
r:ornp lexgrrnoing u il d in N onh ern Cre r:cr:.l. E ssent. Oil Res.,4,
157-159 (1992).
In addition, a number of other unidentified compounds A. Belanger and L. I)ertraze, \lariation intraspacifique dela
rvere also isolated, although no chamazulene and very {'ew compositkm chimique de L'huile essenticlled' ar:hilleem.illefcuilLe.
oxygenated monoterpenes were produced. Rivista Ital. EPPOS, (Numero Speciale),70E-712(1993).
An oil produced from A. millefolitnn ssp. millefolhnn A. C. Figueiredo, M. Salom6, \{. S. S. Pais and J. J. C. Sche{I'er,
haruested in the vicinity of Polar (northeast of Tehran) at an Corttpositiort of tlLeesserftialoil frotrL cell suspensioncultures oJ'
At:hilleamillefolir.trn ssp.millefolium. Plant Cell Tissue Culture,
altitude of 1,900-2,200 m r,vassubjected to iinalvsis by capil-
4 0 . 1 1 3 - 1 1 8( 1 9 9 5 ) .
larv GC (retention indices) and GC/MS by Afsharlpour et al.
S.Af'sharypour,S.Asgan,and G. B. Lockvood,Volutile constiilrcnts
(1996). The components identified were as folkrl'n's,
of Achillea millefolium L. ssp.ntillefolhmtfron lran. Flar'. Fragr.
phenol(3.9%) 6,10,14-trimethethyl-2- I., rr,265-267(1996).
(2.5%)
cls-sabinol pentadecanone-- (0.8%)
trans-caweol(3.7'k) B-caryophyllene (0.9%) Clove Oil
(5.0%)
cls-carveol P-himachalene (1.2%)
(Z)-B-larnesene(2.7"k)
In 1994, Gopalakrishnancompared the changesthat take
bornylacetate(1.3%)
geranylacetate(0.9%) o-patchoulene (2.2%) place when a liquid CO, extract of clove bud and an oi1of
nerylacetate(0.7%) 2-penty-5-propylresorcinol--(1.8%) clove bud are left to stand for 90 davsunder Indian ambient
(Z)-nerolidol
(5.7%) spathulenol (12.4%) conditions.The resultsof this stridvare summarizedin Table
camp he ren on e(1 . 7% ) ( E, E) J ar nes ol( 4. 0) XV Gopalakrishnanconcluded tliat. ol storage,a CO, ex-
4-oxo-3,4-dihydro-2,3- a-bisabolol (22.9%)
tract ofclove bud deteriorated faster than the essentiiJoil.
diazaphenoxatin..(0.9%) campherenone(1.7%)
In 1995,Variyar and Bandyopadhvayused simultaneous
-.independent isneeded
corroboration before canbethought
thesecomponents distillation and extraction (Likens-Nickerson apparatus)to
of asbeingtrueyarrow
constituents
isolate an Indian clove bud oil. Analysiso{ the oil by p:rcked
column GC using compound identific:rtion by peak enrich-
E. Lerriberkovics antl G. Verzar-Petri, Gas chromatographic ment revealedthat the oil had the following composition:
cltaracteri:ation of frequenthl ocatring sesquiterpenes in
essentialolls.J. Chromatogr.,318,125.*31(1985). benzylalcohol(t)
E. Lemberkovics, G. Petri and J. Taryrs, Cos cLtrotmtographic eugenol(64.3%)
detenninatiortof nutno-antlse,squite:enesin sttmecontnrcrcia.l B-caryophyllene (111%)
+ vanillin
Hungarion essential olls. In: Flaxorq,pntl Frogrurtces: a uorlcl (1.9% )
s-humul ene
Edits., B. M. Lar'vrence,B. D. Nlookherjeeand B. j.
per,s1tectiue. eugenylacetate(20.5%)
Willis, pp. 243-247, Elsevier Science Publ. B. V. Arnsterclarn
t = trace (< 0.1%)
(r98s).

136
 results (Lawrence 1979)where the level ofeugenyl acetate
Table XV. Comparativechanges in chemical
in a cold-pressedclove bud oil was found to be around 302r.
composition (%) ot a liquid CO, extract and
an oil of Indian clove bud on storage This same year, Deans et al. (1995) demonstrated that
clove oil exhibited significant antimicrobial activity against
CO, Extract
test micro-organismsand 20 different isolates of Listeria
Oil
monoc!:ltogene , aswell assignificant antioxidant activity. The
90 days 90 days
Compound Fresh
authors further showed that the antimycotic activity of clove
old Fresh old
oil was significantlymore pronounced than its antimicrobial
cr-cubebene 1.5 1.3 0.7 0.6 activi|l.
0-cop ae ne 1. 7 1. 5 1. 0 1.0
B-caryophyllene 16.6 14.7 10.8
More recently, Martini et al. (1gg6) showed that an
9.4
eugenot 62.2 64.8 71.0 72.6 ethanolic extract ofclove buds contained:
isoeugenol* 0.9 0.8 0.6 0.5 B-caryophyllene (4.1o/o)
nerolidol. 1.2 1.2 O.4 1.1 cr-humulene (0.6%)
eugenylacetate 14.3 13.6 12.1 12.8 methyleugenol (0.3%)
farnesol* 0.1 0.3 0.2 0.4 eugenol(60.2%)
. correctisomer eugenylacetate(1.076)
not identified
Furthermore, the authors proved that eugenol was the
mai n fungi r.i dalcomponentof the oi l .
Although the authorsdid not comment to any great extent
B. M. Lawrence, Major tropical ,spices- Cloae.In: Essential oils
on the oil composition,it shouldbe noted that becauseof the
1976-1977,pp. 84-145,Allured Publ. Corp., Carol Stream, IL
method of compound identification the identityof vanillin is ( 1979).
questionable,to saythe least.Also, if vanillin were presenr N. Gop-alakrishnan,Stutdieson the storage quality of C0, extracted
in the oil, it wouid occur in no greater than a trace amounr. cardamomand clooe bud oil s. J. A gric. Food Ch"t"., +2, 796-798
Also in 1995,Fuh et al. evaluatedthe use ofsupercritical (ree4).
fluid extraction (SFE) of clove buds for the purpose of P. S. Variyar and C. Bandyopadhyay, On the aolatiles of cloae,
isolating cr-humulene (noted as u-caryophyllene by the cardamom, nutm.eg and maie. PAF AI, (JanlM ar), I 9-25 ( 1995).
authors), B-caryophyllene,eugenol and eugenyl acetate. M-R.
!. Fuh, W. H. Pan, I. J. Hsieh and C-M. Chuo,
preparatioe
They found that extraction ofpowdered dried clove buds scalesupercriticalJluid extraction of essential oils
from Syzygium
aromaticurn (cloae bucl). American Laboratory, (lec.), 36-+f
at 35"C between 1,500-3,500psi with SFE CO2 yielded
(1ee5).
extractswith the following composition:
S. G. Deans, R. C. Noble, R. Hiltunen, W. Wuryani and L. G.
(0.9-1.0%)
s-humulene Penzes,Antimicrobial anrl antioxidant proper-tiesof Syzygirtttt
(10.2-13.3./")
B-caryophyllene aromaticum (L.) Merr. b Peny: Imltact upon bacteria,
fungi
(75.1-78.8%)
eugenol gnd fatty acicl leael in aging mice. FIav. Fragr. J., IO, 323-3ib
eugenyl
acetate(10.0-10.7%) (1ee5).
H. Martini, M. Weidenbcimer,S.Adams and B. Kunz, Ea genoland
It was surprising to this reviewer that the eugenol was as
c-araacrol:The mainfungicidnl compounds in cloue anrl sauory.
high as reported becauseit indicates a reasonableamount Ital. J. Food Sci.,(r),63-67 (1996).
of eugenyl acetatehydrolysis as compared to some earlier
Progress in Essential Oils
fromPerfumer
Reprinted & Flavorist, 1997,Vol.22, No.4, P. 57
July/August

Peppermint
Oil
In 1981, Takahashiet al. reported that a sample ofpepper-
mint oil produced in Michigan contained germacrene D
(0.807o)and mint sulphideQ.002Eo).
The following year, Chialva et al. (1982) compared the
con-rpositionof the static headspaceof ground peppermint
held at 60oC for 1 h with that of the oil, using GC/MS asthe
metliod of analysis.The results of this study are fbund in
Table I.
Table L Comparativechemical composition (%)
of the oil and headspace ol Mentha piperita
the separation and identification technique, shorved that
there r,verelarge differencesbetween both headspaceanaly-
ses.Also, thesewere very different from the oil composition
(TableII). The compositionof peppermint oil changesasthe
olant matures.but the authorsfailed to take that into consid-
eration. In particul:rr,rnenthofuranis the major constituent
of the flower oil but is a rninor component of the herb oil. It
is alsorecommendedthat in this tlpe of study,the researcher
should obtain the living and han'ested dlnamic headspace
analyseson plantsfron'rthe samepopulation. Finallv,if these
analysesare to be used for comparisonpurposeswitli an oil,
then the oil also should be produced from the same plant
population.

Compound oil Headspace Table ll. Comparativeanalysis (%) of the

cr,{hujene 0 .1 0 .4 dynamic headspaceof living and harvested
cr-ptnene 0 .6 5 .5 peppermintplants and peppermintoil
campnene < 0 .1
B-pinene 1 .3 74 Live plant Harvested Plant
Compound headspace headspace Oil
sabinene 0 .2
myrcene 0 .6 1. 2 hexanal 0 0.1 -
c{,-terpinene 0 .5 1. 0 (Z)-3-hexenal - 0.5
p-cymene 0 .2 (E)-2-hexenal - 0.8
5"3
(Z)-3-hexenol - 0.3
1,8 -cin eo le
Iimonene 1 .9 7. 2 (E)-2-hexenol - t-+

(Z)-B-ocimene 0 .9 1. 7 nexanol - 0.5

T-terprnene 3 .6 2. 7 2,4-hexadienal* -0.1 -
1-octen-3-ol - 2.0
linalool 1 .0
menthone 19.7 23. 7 1,8-cineole 5 '7
isomenthone 2 .7 3. 4 menlnone o.2 12.7 1 8 .1
menthofuran 2 .9 1. 4 isomenthone 9.6 7.7 2 ,3
menthofuran 49.7 26.3 5.2
menthol 3 1.1 1 5 .5
oterpineol 1 .3 neomenthol - Lt

1 .1 menthol t 46.7 44.2

menthylacetate 1 .2 0 .2 neoisomenthol _ 1 .9
isomenthol - o.2
B-bourbonene 0 .5
p-caryophyllene 1 .0 pulegone 1.6 24.5 1 .7
o-humulene t.o 1 3 5- r r ndc eal r i ene't 0.6
6-cadinene 0 .3
" correctisomernot identified
viridiflorol 0 .1 + mixtureof four isomers
t = trace(< 0"1%)

Sevenyearslater, Mookherjee et al. (19E9)comparedthe
resultsof dynamic headspaceanalysis6Taliving peppermint
plant with that of a har-vestedpeppermint plant. Both
headspaceanalysesrverefurther comparedu'ith the analysis
of a commercial oil. The results,baisbdon using GC/MS as
This san-ieyear, Kirichenko et al. (1989) compared the
chemical composition of the oil of a Russianpeppermint
cultivar (Kuban 6) with oils of three so-calledVietnamese
filed mints (of unknown ta-xonomicorigin). The results o{
this studv are found in Tabie III.

138
 Table lll. Comparativecomposition (%) of a Russian Table lV. Comparativechemical composition (%)
peppermintoil with three Vietnamesemint oils of Russian peppermintoil produced from four
commerciallygrown cultivars
Russian Vietnamesemint oils
peppermint CultivarOils
Compound oil
Compound 2 Kubanskaya
6 Krasnodarskaya
Prilukskaya 6 Chernolistnaya
cr-pinene 0. 80 0. 54 0. 62 1.01
3-pine ne 0.69 0.31 0.02 2.88 u {h u j e n e 0.1-0.15 0.1-0.4 0.1-0.2 0. 1- 0. 15
lrmone ne 0. 68 0. 92 1. 36 6.26 0-pinene 0.15-0.2 0.15-0.8 0.15-0.2 0. 1
'1.8-cineole 0. 17 0. 33 1. 88 1.40 camphene 0.2-0.4 0.2-0.65 0.2-0.3 0.3-0.5
sabinene 0.3-0.45 0.3-0.6 0.4-0.6 0.4-0.5
lrans-sabinenehydrate 2. 29 2. 60 1. 51 6.37
menthone 16. 77 2. 28 5. 91 1.76 myrcene 0.3-0.4 0.1-0,3 0.05 0.3-0.5
isomenthone 23.45 2.31 0.49 3.99 1,8-cineole 2.9-3.0 2.4-9.7 1.1 2.4-3.4
menthylacetate 3.75 2.23 4.08 2.74 (Z)-B-ocimene 0.3 0.35-0.9 0.3-0.35
linalool t I I I
neomenthol 2. 00 2. 59 3. 24 0.87
menthol 44.46 80.83 64.87 30.87 menthone 27.1 20.7-31.8 7.6-8.5 25.8-29.2
puregone 0. 99 - 1. 02 1.76 isomenthone 4.0-4.2 5.4-5.5 1 6 . 2 - 1 9 . 5 4.0-4.2
piperitone
+ piperitenone 1. 08 0. 41 1. 46 36.40 menthof
uran
neomenthol 4.5 2.4-3.6 1 . 4 - .15 3.9-4.7

Also in 1989, Brillo analyzed an oil produced from menthol 49-51.2 38.0-5.35 44.0-45.7 53.2-54.2
isomenthol 0.7-1.2 2.2-2.6 0 .5 - 1 .1
peppermint haruestedin tlien-Belorussiaduring flou,ering.
carvotanacetone
0.5-2.3 .0
0.65-1 0 . 1- 0 . 2 0 .3 - 1 .8
The oil was found to contain: piperitone 1.0-1
.2 0.8-1.1 1.2 1 .0 - .3
1
a-pinene(0.14%) + menthofuran
menthone
menthylacetate2.6-3.0 1.7-5.7 1 6 . 6 - 2. 19 1 .6 - 2 .2
B-pinene+ sabinene(0.28%) (37.8%)
B-bourbonene 0.2 0 . 15 - 0 . 2 0.05-0.1 0 .1 - 0 .1 5
myrcene(0.06%) isomenthone(4.65%)
0.5-0.7
B-caryophyllene 1.6-1.9 0.6-0.9 0.3-0.5
limonene(2.06%) isomenthylacetate(0.26%) q,-humulene 0.2-0.6 0.6-1.2 0.5-0.7 0.3-0.5
l,B-cineole+ B-phellandrene menthylacetate(6.94%)
(3.56%) neomenthol + neoisomenthol
mene (0.20'/.)
(Z)-B-oci + B-caryophyllene(10.64%)
p-cymene(0.17o/o) menthol(26.57%) of analysis,Sur et al. (1991) analyzed small amounts o1'
y-terpinene(0.09%) pulegone(1.29%)
(2.19"/")
peppermint leaves and rvater infusions of peppermint.
sabinenehydrate-(0.44%) isomenthol
The hvdrodistillation nrocedure used was similar to the
*
correct isomer not identified
Clevenger-t1pesystem,although the authors used hexane
Using chiral GC analysison a 50 m (3-O-butyryl-2,6-di- in the tran to dissolveall of the oil constituents.Frorr their
O-pentyl)-y-cyclodextrincolurnn, Koenig et al. (1990) analyses,the authors u,ere able to shorv that infusions
confirmed the fact th:rt (-)-rnenthone, (+)-isomenthone, contained menthol (2.6-8.3Eo), menthone (0.7-l.2Vo)and
( )-menthol and (+)-piperitone r'verethe predominant iso- menthyl acetate (3.6-1.4Ea).
mers found in peppermint oil. T\r'oyearslater,Piccagliaand Marotti (1993)usedGC and
Also in 1990, Voronina et al. compared the composition ion trap GC/MS to determine the composition of a sample
of peppermint oil produced from four cultivars of of Italian peppermint oil that \vas producecl in Ozzano
Mentha piperita grown in Russia. From the results (Bologna). The components identified ancl their relative
presentedin Table IY it can be seenthat the oilsrveredevoid amounts can be summarizedas fbllows:
of menthofuran. Becauseof this, it is possible that these cr-pinene (0.69-0.80%) menthone(24.96-28.23%)
cultivars are hybrid forms of' M. piperita selected for the sabinene (0.34-0.45'/.) menthof uran(4.33-9.1 1%)
fJ-pinene (0.81-0.99%) isomenthone (5.27-5.76%)
absenceof menthofuran.
myrcene(O.14-O.26"/.) menthol(46.18-51.93%)
In 1991, Mosandl et al. used multidimensional gaschro- rene(I-0.22%) isomenthol (0.60-0.81 %)
B-phelland
rnatographyusing the technique of "heart cutting" from a a-terpinene(0.15-0.43%) pulegone(0.94-4.24%)
DB-1701 column onto a heptakis (3-O-acetyl-2,6-di-O- p-cymene(t-0.20'/") piperitone(0.33-0.77%)
pentyl)-B-cyclodextrinchiral column to determine the chiral l i m o n e n e( 1 . 3 3 - 1 . 5 2 %) neomenthyl acetate(0.14-0.19%)
(Z)-B-ocimene (0.06-0.26%) menthylacetate(2.96-6.24%)
clistribution of u-pinene, B-pinene and lirnonene in two
(E)-B-ocimene (t) isomenthyl acetate(0.14-0.21%)
san'rplesof peppermint oil. They fbund the enantiomeric
re 1terpinene(0"19-0.31%) B-bourbonene (0.14-0.33%)
rlistribution was: p-menth-2-en-1 -ol. B-caryophyllen e (0.75-2.08%)
( 1 . 0 8 - 1 . 5 8 %) cr-humulene (0.17-0.39%)
(S)-(-)-cr-pinene
(66-70%): (R)-(+)-cr-pi (30-34%)
nen-e
(S)-(-)-0-pi terpinolene (t-0.15%) y-muurolene (0.10-0.30%)
nene(46-48%)
: (R)-(+)-B-pi
nene (52-54'k)
(S)-(-)-l linalool(t-0.93%) germacrene D (1.13-2.59%)
imonene (98%): (R)-(+)-l
imonene (2'k)
isopulegol(1-0.25%) germacrene B (0.13-0.35%)
Using hydrodistillation as the method of oil isolation and *
correct isomer not identified
-C q'ith the inclusionof an intern:rlstandard)asthe lnethod t = tr ac e ( < 0.01% )
 In addition, the authorsdetermined that there were some
Table Vl- Comparativechemical composition (%)
quantitative differences in oil produced from the first
of diflerent peppermintoils
harvestand the secondharvestduring the sameseason.This
difference between oils is reflected in the main oil com-
Gompound Kennewick Michigan Mitcham
ponents shown in Table V.
cI-prnene 1.64 1.34 1 .1 3
campnene 0.02 0.01
Table V. Quantitative composition (%) of peppermint B-pinene 1.97 1.65 1 .4 0
oil produced from different harvest times sabinene 0.93 0.77 0 .6 1
myrcene 0.41 0.33 0 .4 1
Gompound 1st Harvest 2nd Harvest dterpinene 0.46 0.43 0.06
limonene 2.61 2.44 2 .1 9
menthone 26.6 26.6 1,8-cineole
+ B-phellandrene 7.75 7.O2 4.97
menthol 46.4 51.9
menthofuran 4.6 6.7 (Z)-B-ocimene u.c I 0.41 0.37
pu leg on e 3. 9 1. 8 yterpinene 0.68 0"68 0 .1 1
othercomoounds 18.5 13.0 (E)-B-ocimene 0.13 0.11 0.07
p-cymene 0.11 0.24 0.08
terpinolene 0.18 0.18 0 .0 4
When screened against a series of 25 bacterial strains, 3-octanol 0.33 0.30 0.50
peppermint oilwas found (Piccagliaet al. 1993)to possessno /rans-sabinene
hydraie 1.01 1. 1 4 0 .15
antimicrobial activity and almost no antioxidant activity. menthone 17.27 23.14 3 1 .6 4
AIso in 1993, Derbesy et al. reported the results of the menthofuran 7.37 2.48 2.68
analysis of oils obtained from a number of different clones isomenthone 2.53 3.08 6.86
of M. piperi,ta grown in France over a three-year period. linalool 0.30 0.31 0.36
menthylacetate 3.80 3.69 6.66
Although the authors did not distinguish between the clones
in their analyical results, they did show that the oils quanti- neomenthol 3.10 3.25 2.57
B-caryophyllene 0.14 2.24 1 .2 6
tatively varied as follows:
iso(iso)pulegol 0.79 0.78 0 .6 1
o,-pinene(0.45-1.05%) isomenthone(1.23-17.34%) menthol 38.24 38.01 26.78
sabinene(0.20-0.70%) menthofuran (0.12-6.71'/.) puregone t.oJ 1.38 3.78
p-pinene(0.35-1
.37%) neomenthol (1.30-4.78%) o-terpineol 0.14 u. tc
myrcene(0.18-0.91%) menthol(14.44-47.60%) germacrene D 1.33 1.27 0.84
(0.58-7.14'/.) pulegone(0.10-5.40%)
1,8-cineole piperitone 0.46 1 .0 4
limonene(5.28-2.37%) piperitone (0.07-1.20"/.)
trans-sabinene
hydrate menthylacetate(2.48-13.77%) viridiflorol 0.13 0.15 0. 07
(0.01-2.75%) B-caryophyllene (0.58-4.41%)
ment hone( 12. 10 -5 0 .6 0 %g)e rma c re n e D (1 .0 8-3.86% )
period in southwestern Ontario (Canada)over three growing
This reviewer fails to see the value of this data as there seasons.They found that the menthone and isomenthone
were 15 clones of M. piperitd grown and they yielded oils of content was ma-rimized when the plants were immature,
widely varying compositions, as shown above. A more valu- while the menthofuran and pulegone contents increased
able report would have been one giving the chemical compo- along with the flower production. In addition, the menthyl
sition of eachclone'soil over the sametime period. From this acetate level was found to increase substantially over the
clatait could be readily seen whether any of these clones season.A summary of the analyical results obtained from
could become more valuable commercial tlpes rather than this study is shown in Table VII.
the currently cultivated material. The authors further re- The following year,Reverchonet al. (1994)comparedthe
ported that the enantiomersof some key componentswere: compositionof a supercriticalCO, extract (SFE) of pepper-
mint under two separatesetsof conditions with a sample of
(-)-limonene (+)-neomenthol
(-)-menthol (-)-cxterpineol peppermint oil produced by hydrodistillation. Initially, the
(-)-menthyl
acetate authors reported Ihat 0.I7Vo of the SFE extract was com-
prised the following cuticular wa.r hydrocarbons:
This sameyear,Kubeczka(1993)comparedthe chemical
pentacosane(0.5%) methyltriacontane- (1A%)
compositions of peppermint oil produced from two different heptacosane(3.7%) dotriacontane(6.7%)
regions in the United States with ths'composition of an octacosane(1.3%) ethylnonacosane.(0.6%)
oil noted as Mitcham oil (origin unknown). His results are nonacosane (15.5%) e- (2.4%)
ethyltriacontan
shown in Table VI. triacontane(3.6%) triacontane(24.3o/")
ethyloctacosane. (1.4o/o) methyldotriaconiane. (0.3%)
Court et al. (1993)comparedthelaajor component com-
henitriacontane(37.7%\
positionsof peppermint oils produced from plantsharvested
at different stages of development during a four-month *
correct isomer not identified

140
 Table Vll. Comparativechemicalcomposition (%) of peppermint Lipodex E (3-O-butyryl-2,6-di-O-pentyl-y-cyclo-
oil harvested over a four-month period for three seasons dextrin) fused silica column, the authorswere able
to determine that piperitone found at 0.1-1.07oin
Compound J uly August September October the originzrloils existedin the following distribution:
c{,-prnene 0. 61- 0. 97 0.59-0.93 0.52-0.93 o.41-0.82 (aS)-(+)-piperitone
(87->99%)
: (aR)-(-)-piperitone
(t-13%)
B-pinene 0. BB- 1. 32 0. 85- 1. 33 0. 76 - 1 . 3 0 0.65-1.20 t = trace (< 1%)
sabinene 0.46-0.67 0.34-0.64 0.30-0.62 0.31-0.62
myrcene 0.24-0.36 o. 21- 0. 37 o. 17 - 0 . 2 6 0.11-0.31 These same authors (Ravid et al. 1994b, 1g94c)
o-terpinene 0.36-0.45 0.22-O.46 0.24-0.48 0.19-0.40 also used chiral GC columns to examine the
ilmonene 0.26-2.48 0. 22- 2. 11 0.21-1.62 0.22-1
.56 enantiomeric ratio of menthone, isomenthoneand
1,8-cineole 4.88-7.04 4.97-6.81 5.32-6.86 4.47-6.34 pulegone in various peppermint oils. They deter,
T{erpinene 0.66-0.84 0.49-0.85 0.46-0.83 0.40-0.80 mined that these three compounds existed in the
terpinolene 0.14- 0. 19 0. 12- 0. 1I 0. 12 - 0 . 2 0 0.10-0.20 {bllowing enantiomeric ratios:
3-octanol 0.46-0.69 0.63-0.84 0.66-0.84 o.50-0.74
menthone 16.70-32.70 10. 93- 25. 90 2.33-12.30 1.56-4.55 (1S,4R)-(+)-menthone
(Oou")
:
menthofuran 1. 66- 3. 30 2. 11- 8. 85 7.04-8.74 5.37-9.45 (1R,aS)-(-)-menthone
(100%)(1994b)
isomenthone 3. 32- 4. 16 2.10-3.84 (1R,4R)-(+)-isomenthone
(>99-1
00%):
1. 18 - 2 . 4 0 1.04-1
.54
linalool 0.23-0.41 0.25-0.51
(1S,aS)-(-)-isomenthone
(0-<1%)(1994b)
0.20-0.89 0.14-2.06
menthylacetate 1. 77- 6. 83 3.49-8.55 5. 75- 1 4 . 1 2 9.41-22.45 (1R)-(+)-pulegone
(95-990/.)
:
neomenthol 3.23-4.24 3. 10- 4. 68 3.4'1-5.00 3.83-5.00 (1S)-(*)-pulegone
(1-5%)(1994c)
terpinen-4-ol 0. 56- 1. 40 0.70-1.34 0. 72 - 1. 1 2 0.79-1
"1I
Also,Ohloff ( 1994)reportedthat a traceamount
B-caryophyllene 1. 41- 3. 67 1. 61- 3. 07 1. 46 - 2 . 2 9 1.35-3.50
of cls-jasmonewas confirmed as a constituent of
puregone 0.73-1.62 0.89-2.90 0.63-2.90 0.49-1.00
menthol 31.B-44.6 35.9-48.0
peppermint oil.
38.5-57.0 41.4-54.7
Chung et al. (1994) showed that continuous
o-terpineol 0. 21- 0. 37 0.34-0.35 0. 16 - 0 . 3 1 0.14-0.27 cell culture o{ M.
germacreneD 1. 70- 4. 27
piperi.tawassuccessfulin a system
1. 81- 3. 49 1. 65 - 2 . 5 6 1.24-3.20
known as a cell-recycled airlift bioreactor. After
cells were removed from the culture broth, they
The results of the GC/MS analysesof the volatile concen- rvere extractedr,r.ithpentane-methylenechloride (2:1) and
trates of peppermint oil and pepperrnint produced by SFE analyzedby GC. The compounds identified in the extract
can be seen in Table VIII. medium r,vere:
Ravid et al. (1994a)examinedthe enantiomeric distribu-
isomenthol menlnone
tion of piperitone in commercial samples of peppermint limonene methylacetate
from different areasof production. Using a 25 m x 0.25 mm menthol pulegone(majorcomponent)

Table Vlll. Comparativechemical composition (%) of two SFE extracts of peppermintand peppermintoil

SFE-1 SFE-2 SFE-1 SFE-2

Compound (T:50"C,
P:90bar) (T:40"C,
P;120bar) oi l Compound P: 90bar) (T:40"C,
(T:50"C, P:120bar) oil
cI-plnene 0 .4 0 .2 0.3 linalylacetate 0.6 0. 1
B-pinene 0 .7 0 .5 0.5 neomenthylacetate o.2 0.2 0. 2
myrcene 0 .2 0 .2 0.1 bornylacetate 0 0.2 0. 4
3-octanol 0 .1 0 .1 0.1 menthylacetate 9.0 11.7 12.6
oecane 0 .1 isomenthylacetate 0.1 0.2 0. 3
1,8-cineole 5"3 3 .6 3.9 cr,-cuDeoene I t 0. 1
(Z)-B-ocimene na 0 .2 0.3 0.3
B-bourbonene 0.7 0. 6
p-menth-2-en-1
-ol- 0. 2 0 .4 0.2 B-elemene 0.4 0.9 1. 0
menthone 45. 0 Jt). I 35.6 B-caryophyllene 1.8 4.3 4. 5
isomenthone 7.3 7 .5 4.8 B-gurjunene 0.1 0.2 0. 2
neomenthol 1.0 tx-humulene 0.1 I 0. 2
menthol 25.4 2 3 .8 24.8 Q +^"^^^^^^*
P-rqt ilv-gt tv 0.1 0.6 0. 3
isomenthol 0. 5 4. 0.2 0.5 Y-muurotene 0.1 I 0. 3
dihydrocarveol 0. 1 0 .2 0.2 y-cadinene t.o 5.0
pulegone 0. 2 0.3 y-eremene 0.1 0.4
U.J 0.2
piperitone 0. 4 0 .6 0.8 trans-calamenene 0.1 0.4 0. 2
spathulenol 0. 1
caryophylleneoxide o.2 0. 2
T-cadinol 0.6 0. 7
 The following year, Shimizu (1995) reported that pepper-
TablelX. Chemicalcomposition (%)of
mint oil produced in Japan possessedthe following major peppermint oil from plantsproducedin vitro
components: and subculturedfor threedifferenttime periods
limonene(2.8%) neomenthol (3.7%)
1,8-cineole
(7.6%) menthol(41.9o/o) Compound 90-Dayoil 150-Dayoil 180-Dayoil
menthone(22.1o/") menthyl acelale (4.1"k)
isomenthone (3.9%) pulegone(2.1%) o-pinene 2.9 t.J

menthofuran(2"2%) piperitone
(0.2%) B-pinene 3.5 t.o
sabinene 0.3 0.1
This same year, Faber et al. (1995) determined that myrcene 0.2 0.7
capillary chiral GC, coupled with isotope ratio mass spec- limonene 3.6 6.6 96.9
1,8-cineole 0.2 0.1 t
trometry could be used to establisha characteristicisotopic
menthone 0.3 i 1
fingelprint of authentic peppermint oil. Furthermore, the menthofuran ot./ BB.7 2 .5
authors showed that the technioue was very useful in deter- isomenthone 0.7 1

mining the authenticity or gen-uinenessof sample of menthylacetate 1.4 0. 1

"ny neomenthol 0.2 t
peppermint oil.
o-terpineol 0.1 0. 2
Also in 1995, Karasawaet al. used GC and GC/MS to B-caryophyllene 0.1 0.6 I
an:alyzean oil produced from peppermint grown in Ulaan- menthol 24.8 t 0. 3
baatar (Mongolia). The compoundscharacterizedin this oil germacreneD 0.1 0.2 I
piperitone t 0.2 t
were as follows:
B-pinene(0.04"/.) linalool(0.28%)
limonene(0.38%) .crisabinenehydrate(0.24'/")
1,8-cineole (2.47o/o) menthylacetate(9.39%)
p-cymene(0.22%) neomenthol(3.74o/o) Table X. Chemicalcomposition(%) of peppermintoil
2-methylbutyl2- terpinen-4-ol(0.07%)
produced from clonally reproducedpeppermint
methylbutyrate(0.07%) rosefuranoxide (0.05%)
2-methybutylisovalerate neoisomenthol(0.39%) Somaclones Protoclones
(0.08%) menthol(35.07%) Parent
pulegone(O.22o/o)
Compound cfone 1 2
s-octylacetate(0.07%)
3-octanol(0.21%) cr-humulene (0.18%) s-prnene 1.0 1.0 1.0 0.9 0. 2
1-octen-3-ol (0.30%) d,-terpineol (0.06%) B-pinene 1-4 1.3 1.4 1.3 0. 4
cls-linalooloxide{uranoid(t) borneol(0.05%) sabinene 0.7 0.7 0.7 0.6 0. 2
menthone(32.22'/') germacreneD (0.05%) myrcene 0.3 0.3 0.3 0.2 0. 1
/rans-sabinene hydrate(t) piperitone (1,32o/") limonene 2.0 1.6 1.9 1.2 0. 8
(Z)-3-hexenylisovalerate carvone(0.16%) 1,8-cineole 6.3 5.7 6.2 6.0 5. 7
(0.06%) 6-cadinene (0.16%) (Z)-B-ocimene 0.1 0.1 0.1 - 0. 1
menthofuran (O.07%) geraniol(0.05%) yterpinene 0. 1
isomenthone(5.43%) crijasmone (0.O4'/") p-cymene 0.1
B-bourbonene + benzalde- (Z)-nerolidol (0.06%) terpinolene 0.1 0. 1
hyde(0.31%) viridiflorol(0.09%) isoamylisovalerate 0. 1
camphor(0.42%) 3-octanol 0.1 0.t 0.1 0.1 0. 4
menthone 2B.O 27.5 26.8 't7.8 24.1
t = trace (< 0.01%) frans-sabinene
hydrate 3.0 3.2 2.5 2.1 1. B
Mucciarello et al. (1995)establishedin-vitro culture of M. menthofuran - 8. 8
piperita startingwith nodal segmentsof mature plants.After isomenthone 9.3 4.7 4.1 4.0 4.0
30 days of culture, arillary buds were cut from each nodal B-bourbonene 0.3 0.3 o.4 0.9 0. 2
segment and cultured for 180 days, subculturing every 30 neomenthylacetate 0.2 0.2 0,2 0.2 0. 2
linalool 0.3 0.3 0.3 0.4 0. 5
davs.Essentialoils thatwere produced from in-vitro growing menthylacetate 2.8 2.9 3,2 2.5 3. 1
plants were subjected to capillary GC analysis.It was deter- B-caryophyllene 3.2 4.0 J-+ 5.2 1, 4
rnined that oils produced from plants subcultured fbr 90 neomenthol +
davs, 150 days and 180 days possesseddifferent composi- terpinen-4-ol 2.8 2.9 3.2 3.4 3. 1
neoisomenthol 0.3 0.4 0.4 0.7 0. 3
tions, ascan be seenin Table IX. These resultsshow that the puregone 2. 8
3.5 3.0 3.7 3.3
oils produced from the in-vitro subcultured plants can be menthol 31.8 32.2 33.3 40.4 37.4
thought of as being from three distinct phenotypes. isomenthol 0.6 0.8 0.6 0.8
Leaf-derivedprotoplastsof M. piperituwere regenerated (E)-B{arnesene 0.2 0.1 0.2 0.2 0. 7
o-terpineol+
bv Okuyamaet al. (1995)to produce a,numberof protoclones.
germacreneD 3.9 4.4 3.6 5.7 1 .6
Theseprotocloneswere grown on a plantation alongwith the piperitone 0.8 1.0 0.7 1.5 1 .0
nother plants. Oils produced from the plantswere analyzed piperitol- 0.2 0.2 0.2 0.3
bvacombination of GC and GC/MS, the resultsofwhich can viridiflorol 2.0 1.0 t.o 0.7 0.4
be seenin Table X. It is of interest to note that there was not . correctisomernot identified
a great deal ofvariability in the oil produced from the parent
clone,somaclones(variantclonesderived from same-parent Finally, I would like to correct an error detected by
clone) or protoclones (variant clones derived from same- B. Ridley (1994). In a previous review (Lawrence 1993)
parent protoplast). I reported that Maurer and Hauser ( 1988 ) identified p-cresyl
The followingyear, Fenin (1996) also analyzedthe oils phenylacetate and p-cresyl isovalerate in peppermint oil.
produced from peppermint plants originally propagatedin In actual fact, the authors searched for these compounds
vitro, prior to field cultivation. An in-vitro propagation can and were unable to detect them as constituents of the oil.
lead to somaclonalvariant production. As a result, the sec- Thanks is extended to Ridley for bringing this information
ondary metabolitecomposition(in this casethe essentialoil) to my attention.
may not duplicatethat of the parent. The dataobtained from
the analysisof nine oils derived from a cross section of K. Takahashi, S. Muraki and T. Yoshida, Sqnthesesand distribution
variants can be seen in Table XI. of (-)-mintsulphide, a nouel sulfu r-contai n i ng sesquiterpene.
Agric. Biol. Chem.,45, 129-131(1981).
Also in 1996,Zheljazkov et al. determined that the vari-
abiliq, in oil composition of Bulgarian peppermint that had F. Chialva, G. Gabri, P. O. P. Liddle and F. Ulian, Quantitatioe
et:aluation of aromaticherbsby directheadspace (Ce )2onalysis.
been cultivated using either mechanicalweed control, chemi- Applications of the method and comparison uith the traditlonal
cal weed control or both was small. The compoundsidenti- analysis of essential oils. In: Aromaiic plants. basic and applied
fied in the oil, and their quantitativevariance.lssummarized aspects.Edits., N. Margaris,A. Koedam and D. Vokou, pp. 183-
as follows: 195, Martinus Nrlhoff Publishers,The Hague, (1982).
B. Maurer and A. Hauser, lfuntification de ceftains produits
(0.72-0.77%)
cr-pinene menthofuran (4.90-5.65%)
aromatisants dans des ar6mes. Parfum. Cosmet. Ar6mes, (82),
sabinene(0.68-0.75%) isomenthone (4.68-5.20./.)
69-72(1988).
(0.61-0.72%)
B-pinene menthylacetate(8.92-9.90%)
myrcene(0.43-0.47o/o) B-caryophyllene(3.98-4.20.k) B. D. Mookherjee, R. A. Wilson, R. W. Trenlde, M. J. Zampino and
limonene(0.53-0.64%) neomenthol(7.07-7.59%) K. P. Sands, Neu dim.ensionsin flaoor research. Herbs and
1,8-cineole(3.53-3.60%) neoisomenthol(1.57-1.60%) Spices. In: Flaoor chemistry trends and deoelopments. E dlts ., R .
yterpinene(0.44-0.55%) menthol(37.0e-39.60%) Teranishi,R. G. Butteryand F. Shahidi,pp. 176-187,ACS Symp.
p-cymene (0-0.15%) pulegone(2.01-2.30%) Series,Amer. Chem. Soc.,Washington,DC (1989).
hexanol**(0.15-0.19%) carvonet(1.41-1.607") E. B. Kirichenko, L-D. Ky and V. A. Mel'nikov, Essential oil
menthone (12.40-1
6.3oo/o) compositionof someVieinttmesemint aarieties.Byull. GI. Bot.
Sada,154, 56-69 (1989).
"* orobablv 3-octanol not hexanol
t probably piperitonenot carvone

Table Xl. Variationin chemicalcomposition (%) of peppermintoil from plants produced in vitro and grown in France

Compound 1 2 3 4 5 6 7
0-prnene 0 .6 < 0 .1 0.7 0.5 0.6 u.t 0.9 0.8 r.0
B-pinene 1 .0 0.2 0.8 0.6 0.7 o.7 0.9 0.9 1 .4
sabinene 0.5 0.2 0.3 0.3 0.3 0.3 NA 0.6 0 .8
myrcene 0 .4 1 .8 0.6 o.4 1.1 0.5 0.8 2.5 0 .3
0-terpinene 0 .2 0 .2 < 0.1 <0 . 1
limonene ' to 0 .4 2.O 1.8 1.0 1.9 3.4 13.1 4 .1
1,8-cineole 6 .0 t.J 0.1 0.3 0.4 0.2 1.8 5 .8
(Z)-B-ocimene 0.2 0.4 <0.1 0.1 0.2 o.2 o.2 0.2
(E)-B-ocimene < 0 .1 0 .1 <0.1 <0.1 <0.1 <0 . 1 0.1 <0.1
y-terpinene 0.4 <u. I 0.1 <0.1
p-cymene 0 .2
octanol 03 < 0.1 09 0.3 0. 3
frans-sabinene
hydrate 1 .0 < 0.1 2.0 2.O
linalool 78.3
menthone p .; 0 .4 7.5 7.3 ?.; 10.7 o.7 10 . 0
menthofuran <0.1 0" 6 0.5 - 7.8
isomenthone 2 .7 u-z 2.0 aa 2-1 4.0 0.; - 2.1
menthylacetate 7 .4 0 .3 11 . 8 4.0 1.3 t.J 0.8 7.8
isomenthylacetate 0 .4 0-2 < 0.1 0.2 < 0.1 0.5
neomenthol 4.4 2.2 3.0 1.8 2.2 1.; - 3. 8
p-caryophyllene 0 .7 o- z 1.1 0.1 < 0.1 0.3 0.1 1.7 2. 0
puregone 0.8 t*0.1 0.2 42.8 0.2 38.4 25.6 54.2 0.7
menthone 50.8 0.9 57.5 30.0 78.1 33.2 10.6 2.8 41.0
isomenthol 1. l 0.3 0.7 0.3 0.6 - 0. 9
o-terpineol 0.5 \.r <0.1 < 0.1 0.2 0.2 - 0-4
germacreneD 0.5 0.3 1.4 0.2 0.3 0"4 0.; 1.4 1. 7
carvone - 1. 1 0.4 14.2 - 0. 3
piperitone 0. 6 0.6 0.5 0.8 14.3 0.4 0.4
\'. A. Brillo, Compo,sition of the Essential Oil of Peppennint oil and its inLpoftance in the atthenticity control. J. Essent. Oil
C rou;n in B elorussia.Vesti Akad. N ar-LrkB SSR Ser. Biyal. N avuk, Res.,7, 123-13r (1995).
(4 ), 11 -14(19 89 ).
D. Karasawa,S. Shatar,A. Erdenechimeg,Y. Okamoto, H. Tateba
\V. A. Koenig, R. Krebber, P. Evers and G. Bruhn, Stereochemical and S. Shirnizu, A stuchlon Mongoliatt tttints.A new chemotype
analqsis of constituents of e,s,sentialoils and flaxor cornpouncls Jrom l,[entha a,siaticoBorciss ond constituents of IV. arnensi,sL.
by enantioselectioecapillary gaschromatogrryh.LJI. High Resol. and.M. piperita L, J. Essent.Oil. Res.,7, 255-260(1995).
Chron.ratogr.,f3, 328-$2 (f990). M. Mucciarello, T. Sacco, M. Bricarello, S. Scannerini and M.
E. P. \loronina, L. B. Dmitriev and L I. Grandberg,Contpositionof Maffei, Oli e,s,senziali
d.i Mentha x piperita micrcpropagation in
essentialoil of ceftairt, mint speciesand aarieties introdtrced in oifro. Rivista Ital. EPPOS, (17), 10-30 (1995).
Central Botanic Carclen. Izv. Timiryazevsk. S-kh. Akad., (a), S. Ok-uyama,H. Sato,K. Hosomi, S. Enomoto, S. Oka,Y. Ito and M.
(ree0).
166-r70 Uzawa, Protoclonal aariatictns in essential oil cornpositiort,of
-\. \Iosandl, K. Fischer, U. Hener, P. Kreis, K. Rettinger, V. plants regenerated.frotn protoplasts tf peppemtint (Mentha
Sclrubertand H. G. Schmarr,Stereoisomericflaxorconrpounds piperita L.). Nippon Nogei KagakuKaishi, 69,33-36 (1995).
18. Clilrospecific analqsis of natural .flat:ors and essential oils Ph. Fenin, La rnicropropagation in xitro au seruice cle la filidre
ttsing nultidimensional gas chromatography. J. Agric. Food "plantes ri parfum, aronmtiques et nddicinales, " Rivista Ital.
Chern.,39, 1134-1139(1991). EPPOS,(NurneroSpeciale),327-346(1996).
S. \-. Sur, F. M. Tuljupa and L. I. Sur, Gas chromatographic V. Zheljazkov, B. Yankov anclV. Topalov, EJfect of nwchanical and
rldennination of monote:enes in es,sentialoil of medicinal chemical u;eecl controL on the grouth, detelopment and.
pl ants.l. Chromatogr.,542, 451-,158( 1991). prorluctit:ity of MentLLa piperita and Mentha aruansis uar.
B. \1. Larvrence, Progress in essential olls. Perfum. Flavor., l8(4), y'tiperascens grou^nfor planting m.uterial.J. Essent.Oil Res., 8,
5e-72(1993). r 7 1 - 1 7 6( 1 9 9 6 ) .
R. Piccaglia and M. Marotti, Characterization of seue,ralantmatic
plarftsgrouninNorthemltafuT. Flav.Fragr. J.,8, f 15-122(1993). N utmeg Oi l
R. Picaglia,M. Marotti, E. Giovanelli,S.G. Deansand E. Eaglesham, Using retention time data and compound co-injection on a
-\ttibacterial and antioxiclant properties of Mediterranean packed GC column, Madhavanet al. (1991) reported on the
ttronntic plants. Indust. Crops Products,(2),47-50 (f993).
analysis of oils obtained from nutlneg leaves and flowers
\{. Derbesv,R. Uzio, D. BoyerandV. Cozon,Corftributiortdl'dtude
(Mqristica Jragrans) of Indian origin. The results of this
dc l'Lndlle essentiellerJe Menthe-Mentha piperita. Rivista Ital.
EPPOS,(Numero Speciale),537-543(1993). study are summarizedin T:rbleXII. Although these oils are
K. H Kubeczka,M dglichheitenund grenzender qu alittitsbeu ft eih t ng not generally used commercially, their composition was
r:t-:neilich uenoindeter ritheri,iclrcr Ole. Ln, Atlrcrisclrc Ole- reviervedin light of the possibilitythat nutmeg leaf oil could
tirlsptltch und uirklichkeit. Edit., R. Carle, pp. 85-102, be used as il diluent for nutmeg oil.
\\-issenschaft.Verlag. mbh Stuttgart ( 1993). This sameyear, Pino et al. (199f ; used a combination of
\1-.\. Court, R. C. RoyandR. Pocs,Effectofharaestdateonthetlield column chromatography and GC indices on two capillary
t;nd qualitrJ of the essentialoil of peppermint. Can. I. Plant columns (one polar and one nonpolar). The compounds
Sci..73, 815-824(1993).
characterized in an oil produced {rom nutmegs obtained
E. Rererchon,A. Ambruosi and F. Senatore,Isolationofpeppennint
fron'i Grenada were as follows:
,,.i1usingsupercritical COrextntction. Flav. Fragr. J., 9, 19-23
1994). (1.2%)
cr-thujene 8-cadinene (<0.1%)
E Ridlev, personalcommunication (199ab). (10.2o/o)
o,-pinene 1,8-cineole (0.8%)
camphene (<0.1%) trans-sabinene hydrate(2.4"/")
I- Rar-id,E. Putievsly and L Katzir, Enantiorneric distribution of
B-pinene(8.0%) citronellol(<0.1%)
piperitone in e,ssentialoils of sonrc Mentha spp., Calamintha (57.0%)
sabinene decanal (<0.1%)
incana(Sm) Heldr. and,Afternisiajudaica L Flav. Fragr. j., 9, 85
myrcene (2.2"k) linalool(0.2%)
1994).
D-3-carene (0.3%) cis-sabinene hydrate(0.8%)
I- Rarjd, E. Putievs\y and L Katzir, Chiral C C analqsi s oJ'menth one cx-phellandrene (0.3%) camphor (0.1%)
and isomenthoneu;ith high enantiomeric purities in laboratory- o-terpinene (0.9%) bornylacetate (0.1o,",7
rrrudeand conutTercialessentioloils. Flav. Fragr. J., 9, 139-142 limonene(2.9%) terpinen-4-ol (6.4%)
1994). y-terpinene (1.7%) citronellylacetate(<0.1%)
L Ravid, E. PutievsLT ancl L Katzir, CC analqsi,sof (1R)-(+)- p-cymene (1.0%) o-terpineol (0.3%)
pulegone uith high enantiomeric purity in essential oils of sonrc terpinolene (0.4%) geranylacetate(0.2%)
Laniaceae arom.aticplants.Flav. Fragr. J., 9, 205-207 (1994). d-cubebene (<0.1%) geraniol (<0.1%)
o-copaene (0.3%) methyl eugenol (0.1%)
G Ohloff, Scentand fra.grances. Thefascinotion of odors and their
s-bergamotene" (< 0.1% ) eugenol (< 0.1% )
clrcmical Tterspectioes.
Translated W. Pickenhagenand B. M.
Lawrence.p. 223. Springer Verlag, Berlin Heidelberg (1994). B -caryophyl l ene(< 0.1% )el emi ci n(0.7% )
B-bisabolene (<0.1%) myristicin (0.9%)
I. S. Chung, Y. M. Kang,J. H. Oh, T. Khr, H.$ Lee and Y. A. Chae,
Continuou,s suspencleclcell culture of Mentha piperita in cell-
recycled,aillffi bioreactr.rr.Biotechnol:-{echniques, 8, 7 82-792
(l 9 94 ). The next year,Konig et al. (1992) examinedthe enantio-
meric proportions of the monoterpene hydrocarbons in
S. Shimizu, Ltlentha piperita and Japane.sbMentha aruensis uar.
piperascens.Aromatopia, 4(4), f0-f4 (1995). nutmeg oil using capillary chiral GC analysison either a
B. Faber, B. Kraus,A. Dietrich and A. M osandl, G aschrornatography 6-methyl-2,3-di-pentyl-B-cyclodextrincolurrn or a 6-
- isotope ratio massspectrometnJin the onolysis of peppemtint rnethyl-2,3-di-pentyl-y-cyclodextrincolumn. They found
 o-terpinene + p-cymene bornylacetate(0.07o/o)
Table Xll. Comparativechemical composition (%) ( 1 . 0 8 %) methyleugenol(O.14%)
of nutmeg leaf and flower oil 1,8-cineole + limonene eugenol+ o-terpinylacetate
( 6 . 1 8 %) (0-22./")
Nutmeg Nutmeg B-phellandrene (1.08%) geranylacetate+ 0-copaene
Compound leaf oil flower oil y-terpinene(0.54o/.) (0.2e%)
Iinalool+ terpinolene (O.48%) (Z)-isoeugenol (0.31%)
CI-prnene 8.62-34.64 9.51
B-terpineol-(0.25%) B-caryophyllene + (E)-isoeugenol
campnene 0-0.57 0.49 borneolt(0.05./.) (0-07%)
sabinene+ B-pinene 25.95-38.90 14.05 terpinen-4-ol (1.85%) a-humulene(0.O2%)
myrcene+ cr-phellandrene 2.92-7.55 4.42 ct-terpineol + piperitol- 6-cadinene (0.08%)
6-3-carene 0.70-2.08 (0.36%) myristicin(3.28%)
crterpinene 2.51-6.48 J.O I
geraniol(0.02o/") e l e m i c i n( 1 . 3 8 %)
p-cymene 2.49-4.78 4.55 safrole+ p-cymen-B-ol myristicacid (0.01%)
ltmonene 4. 17- 8. 96 4.40 (0.53%) triglycerylmyristate(0.06%)
+ 1,8-cineole
B-phellandrene 1. 79- 4. 59 1- 4 6 - 4 . 4 1
1. 80- 5. 96 - correct isomer not identitied
Y-terprnene 4.63 r tentativeidentification
linalool 0. 95- 2. 17 3.95
terpinolene 0-0.28 0.48 The reasonfor the occurrenceof mixed ouantitativedatalr,as
B-terpineol- 0-0.21 0.36 that the oil r,vasseparatedusing a packed GC column rather
borneol 0-0.09 0.14 than a capillary GC column.
terpinen-4-ol 1. 89- 6. 78 11.63 Using a chiral phase {used silica column, Ravicl et al.
0-terpineol 0.35-1.74 5.BB (1992) determined that the enantiomeric distribution of
geranrol 0.02-0.08 terpinen-4-ol, which was found at 4.9Voin nutmeg oil, was
bornylacetate+ o-fenchylacetate 0-0.59 0.31 ( S)-( + )-(737o
), (R )- (* )-(277" ).
terpinen-4-ylacetate o.32-2.82 0.46
o-terpinylacetate
In 1995,Variyarand Bandyopadhyayanalyzeda sampleof'
0.02-0.47 0.64
Indian nutmeg oil produced by using a Likens-Nickerson
geranylacetate 0.51-1.42 0.31 sirnultaneousdistillation and extraction apparatus.The oil,
B-caryophyllene 0-0.07 0 . 10
methyleugenol 0. 17- 0, 48
which was analyzedby packed column GC and component
0.58
eugenol 0. 10- 2. 16 0.71 identification b;' peak enrichment, was reported to contain:
(Z)-isoeugenol 0. 14- 1. 00 0.63 o-pinene(7.8%) a-terpineol(1.0%)
nerolidol* 0- 1. 86 0.96 B-pinene+ sabinene(38/%) eugenol(1.3olo)
(E)-isoeugenol 0-0.40 0.56 myrcene(3.4%) B-caryophyllene (0.2%)
myristicin 0.44-1.85 3.79 l i m o n e n e( 3 . 1 %) (5.0%)
myristicin
elemicin 0. 19- 3. 51 8.76 linalool(0.8%) elemicin(2.6%)
terpinen-4-ol (8.6%)
- correctisomernot identified

Also in 1995, Dorman et al. showed that nutmeg oil

clemonstrated extensive antioxidant activity, similar in exlent
that the monoterpene hydrocarbon {raction of East Indian
to thaf olthynre and oregano oils.
nutmeg oil contained the fbllowing:
The following year, Ravid et al. (1996) examined the
(+)-a-thujene(0.19%) (+)-o-phellandrene (0.82%) enantiomeric distribution of borneol in a commercial samnle
(-)-cr-thujene
(1.66%) (-)-5-3-carene(1.43o/") of nutmeg oil. Using chiral GC analysis on a permethylaled
(-)-cr-pinene
(21.74%) o-terpinene (3.69%)
(+)-u-pinene(5.69%) p-cymene(1.49%) B-cyclodextrin column, borneol, r,vhich was found at 0.3%
(-)-camphene (0.36%) (-)-B-phellandrene (0.20%) in the oil, had the follorving distribution:
(-)-B-pinene(10.60%) (+)-B-phellandrene (2.39"k) (lR)-(+)-borneol
(27%): (lS)-(-)-borneot
(73%)
(+)-B-pinene(7.65%) (-)-limonene(3.47%)
{+)-sabinene(26.84%) (+)-limonene (2.23%)
(-)-sabinene L. Madhavtrn,IvI. Gopalakrishnanand C. S. Naravanan,Clrcmical
(0.51%) y-terpinene(4.94%)
myrcene(2.88%) coml:osition of ruttnrcg lrof arrclfloutr oils. Indian Perfurn.,
terpinolene(2.28%)
3 5 ( 3 ) , 1 6 1 - 1 6 3( 1 e 9 1 ) .
Li adclition,the authors rvere able to show tliat the oll dld J. A. Pino, P. Borgesand B. Mollincdo, Nota. aceiteesenciolde nuez
Lrt containanv (+)-camphene,(-)-u-phell:rndreneor (+)-6- rnoscada(Mqristicalragrons H.): obteru:ionq caracterizrLciondc
. -t . ll' e n c . su composcioncluitnica.Rev. Agroquim. Technol. Alirnent., 31,
4 r 1 - 4 1 6( 1 9 9 1 ) .
-\lso in 1992, Gopalaklishnan compared the chemical
\'V. A. K6nig, A. Krtiger, D. Icheln and T. Runge, Enantionrcric
- -,npositior-rof mace and nutmeg o-il produced from M.
cotrtpositionof the chiral ('onstituentsitt ts,scntialoils. Port f :
''t:zrons grown in local gardensin Tr.ivandmrn(India). The noriote:ene'hy drocarbons.j. High Resol.Chromatogr-..15.
' rl ) oundsideniilje di n n u fm e go i l w e re : 184-189(1ee2).
.r-pinene
(14.72%) (3.06%)
c-phellandrene M. Gopalakrishna\ Chemical conrytositionof nutunegand nrtce.
:-pinene
+ sabinene
(62.660/") (0.60%)
6-3-carene l. SpicesAromat. Crops,l, 49-54 (1992).
U. Rar.id, E. Putievslqr,I. Katzir and R. Ikan, Detemtination of the (E)-2-hexenal (0.1-0.2%) cis-sabinenehydrate(0.1-0.4%)
enantiotnericcornpo,sition rf teryinen-4-olin essentialoilsusing a-thujene(3.0-3.4%) frans-p-menth-2-en- 1-ol
o pemtethylated ftcyclodextrin coated chiral capillanl ctthunn. a - p i n e n e( 1 . 0 - 1
. 1 %) (trace-0.1%)
Flar. Fragr.J. 7. 49-52( 1992\. camphene(0.1%) b{erpineol(0-0.1%)
1-octen-3-ol (0.3%) terpinen-4-ol (1.1-1.2%)
P. S. \'arivar and C. Bandyopadhyai', On the uolatiles of cloae,
3-octanone (0.1%) oterpineol(0.1%)
ca r d anut rn, mltnTeg ancl rrtc e. PAFAI, (Jan/M ar), 19-25 ( 1995)
sabinene(0.5%) thymol(35.4-46.7%)
H J. D Dorman, S. G. Deans,R. C. Noble and P. Surai,Eoaluation carvacrol(0.6-0.8%)
B-pinene(0.4%)
in titrc.tplant e,ssentialoils as notural antittridants. j. Essent. Oil myrcene(3.1-3.3%) eugenol(0.3-10.7%)
Res..7, 645-65r (1995) o-phellandrene (0.3-0.1 %) methylcinnamate(t-0.1 %)
L. Rarid, tr. Putievslcyand I. Katzir, Sterenchemicalanalqsisof 6-3-carene(0.2olo) methyleugenol(t'0.1%)
bonrcol in essential oils usingpermethylated ftcycloclextrin as o-terpinene (1.0-3.0%) o-copaene(0.4%)
a cliral stationarLlphase.FIav. Fragr. J., ff, 191-f95 (1996). p-cymene(5.8-18.3%) B - e l e m e n(e0 . 1 %)
1,8-cineole (0.3-3.5%) (E)-BJarnesene (t-0.1%)
Ocimumgratissimum Oil l i m o n e n e( 0 . 9 - 1 " 0 %) cr-humulene (0.2%)
(Z)-B-ocimene (1.B-3.4%) (E)-methyl isoeugenol (0.1-0.2%)
In 1986, Yu and Cheng reported the results of a combined (E)-B-ocimene (0.2-0.3%) germacrene D (t-0.1%)
GC and GC/MS analysisof a ChineseOcimum gratissinrum y{erpinene(3.4-22.5%) B-selinengt (0.9-1.5%)
oil. The compounds identified in this oil were: trans-sabinene hydrate o_farnesene.r(t_0.1%)
( 0 . 4 - 1 . 5 %) B-bisabolene (t-0.1%)
3-hexenol*(0.08%) terpinen-4-ol(0.34%) a-p-dimethylstyrene (0.9-1.0%) T-cadinene(0.1-0.2'/.)
crthujene(0.06%) linalool(0.14%) terpinolene (0.1%) 6-cadinene(0.3-0.4'l")
a-pinene(0.05%) eugenol(80.33%) linalool(0.2-0.3%) caryophyllene oxide(0.3-1.3%)
sabinene(0.14'/.) B-caryophyllene (0.73%)
myrcene(0.16%) cr-humulene (0.05%)
t tentativeidentification
p-ocimene-(12.89'/") B-cubebene(4.24'/.) t = trace (< 0.'1%)
cr-ocimene* (0.27%) cadinene*(0.06%)
y-terpinene(0.02%) T-muurolol(O.02'/.) The following year,Khanna et al. (1988)reported that the
* correct isomer not identified main componentsof clocimum oil (a eugenol-richselection
of O. gratissim,um growTtin India) were:
It is presumed that because the cclmpounds rvere
presented in elution order from a non-poiar capillary CC ocimene.(0.28'/.) linalool(2.35%)
bornylene**(0.56%) methylchavicol(4.95%)
column that the p-ocimene and o-ocimene were, in fact,
(0.43%)
o(-terpinene eugenol(77.60'/.)
incomplete characterizationsof (Z)-B-ocimene and (E)- camphor(2.50%) methyleugenol(5.81%)
B-ocimene,respectively.In addition, becauseof the elution p-cymene(0.56%) B-caryophyl lene (4.32'k)
order presented,it shouldbe noted that the characterization
* correct isomer not identilied
of B-cubebenewas in error. **
constituentidentity in question
Also in 1986, Zamureenko et al. examinedthe composi-
tion of ten oils cf Ocimun gratissinwm produced in the In 1988, Maia et al. reported that an oil produced from
former Soviet Union as a source of eugenol. The oils were O. grati,ssimtnnof Brazilian origin was found to contain:
found to contain: cr-pinene(1.33o/o) terpinen-4-ol(O.47'/")
sabinene(0.85%) cr-terpineol (0.92%)
cr-pinene(0-0.4%) camphor(0-6.7%)
B-pinene(0.68%) t h y m o l( 1 3 . 11 %)
camphene(0-0"3%) terpinen-4-ol(t-0.9%)
myrcene(5.640/0) carvacrol(0.87'/")
B-pinene(0-0.4'/") menthol(O-0.2'/")
p-cymene(29.69%) B-caryophyl lene (2.01'k)
myrcene(0-0.3%) eugenol(31.5-90.5%)
T-terpinene(0.29%) allo-aromadendrenet (5.26%)
p-cymene(0-0.6%) cr-cubebene (0.2-3.3'/.)
s-thujone(0.50%) (E)-B{arnesene (18.99%)
1,8-cineole (0-0-2%) o,-copaene(0.1-1.3%)
(0.1-1.5%) borneol(1.38%)
limonene(0-0.4%) B-bourbonene
(Z)-B-ocimene (0.3-14.5%) B-caryophyllen e (1.2-6.5%) r tentativeidentification
(E)-B-ocimene (tace- 12.1"/') p-cubebenet (0.1-0.3%)
3-3-carene (0-10.9%) cr-humulene (t-0.5%) In 1990, Vostrowsly et al. used modern analltical tech-
yterpinene(0-0.3%) germacreneD (1.8-15.7"/") niques to analyze an oil produced from O. grati'ssimunt
frans-sabinene hydrate 6-cadinene (0.7-1.6%)
har-vestedin the An'razonregion of Brazil. The oil, which
(t-0.3%) T-muurolol(0-0.1%)
terpinolene (0-t) cadinenol(0-0.1%) did not have a chemical composition of economic
linalool(0.1-0.7%) (0.1-0.2%)
cr-cadinol tance, possessed the following composition:

t = trace (< 0.01%); t incorrectidentitybased on elution order tricyclene(t) myrcene(0.35%)

othujene (t) 3-octanol(0.08%)
A year later, Ntezurubanzaet al. (1987) shor'ved,through cr-pinene(0.27o/o) a-terpinene(0.14'/.)
GC/MS analysis,that RwandanO.grqlissimum oil possessed camphene(0.14%) limonene(0.20%)
a compositiondifferent from the eugenol-richoils normally benzaldehyde(t) 1,8-cineole(3.28"/")
sabinene(0.80%) (Z)-B-ocimene (3.65%)
associatedwith the species.Two samples of Rwandan O
B-pinene(0.44'/") (E)-B-ocimene (0.33%)
gratissimurnoil possessedthe following composition: 1-octen-3-ol (0.15%) T-terpinene(0.07'/.)
 terpinolene (0.11%) methylcinnamate(t) terpinen-4-ol(0.4%) (Z)-o-bisabolen
e (2.3%)
linalool(1.32%) B-elemene(2.03%) methylchavicol(2O.6%) caryophylleneoxide(0.2%)
myrcenol(0.19%) methyleugenol(46.83o/o) (0.5%)
o,-terpineol methyleugenol(0.1%)
terpinen-4-ol(t) B-caryophyllene(5.50%) germacreneD (3.9%) eugenol(4.6%)
(0.31%)
ct,-terpineol cr-humulene(1.43o/o) bicyclogermacrene (1.7ok) T-cadinol(3.1%)
methylchavicol(t) allo-aromadendrene (0.40%) B-bisabolene (0.8%)
8-elemene(0.17%) aromadendrene+ germacreneD
eugenol(19.26%) (5.74%)
A suwey of someother strainsof O. gratissinrumrevealed
the existence of the second chemotlpe, although this
AIso in 1990,Wu et al. examinedthe chemical composi- chemotype possesseda composition with considerable
tion of a eugenol-rich strain of O. grati,ssi,mum.
They found quantitative variation as shou'n belolv,
that the oil contained the following constituents: camphene(t-0.6%) (0.2-4.5o/")
B-elemene
3-hexenol.(0.05%) (0.09%)
cI-terpineol B-pinene(t-0.5ol.) B-caryophyllen e (2.5-27.3%)
c-thujene(0.01%) eugenol(84.50%) sabinene(0.1-0.6%) terpinen-4-ol(t-O.2%)
a-pinene(0.03%) c-copaene(0.52o/o) myrcene(t-0.5%) methylchavicol(0.4-2.O%)
sabinene(0.03%) isocaryophyllen e (1.52%) 1,8-cineole(0.1-30.9%) crterpineol(0.1-0.3%)
myrcene(0.10%) cx-humulene (0.10%) (Z)-B-ocimene (1.O-4.0%) germacreneD (3.5-1 0.9%)
p-cymene(0.10olo) y-muurolene(0.07%) (E)-B-ocimene (t-0.6%) bicyclogermacrene (t-9"2%)
(Z)-B-ocimene (4.57o/o) allo-aromadendrene (0.50%) p-cymene(t-0.1%) B-bisabolene (0.1-0.2'/")
(E)-B-ocimene (0.20'/") cr-muurolene (2.43%) terpinolene(t-0.1o/.) (Z)-cx-bisabolene (0.1-0.2%)
T-terpinene(0.06%) s-cadinene(0.96%) 1-octen-3-ol (1.0-1.6%) caryophyllene oxide(t-0.39"7
linalo ol(0 .14 % ) cedrol(0.37%) camphor(0.4-0.6%) methyleugenol(0.1-1.9%)
terpinen-4-ol(0.28o/o) l i n a l o o(l0 . 1 - 3 . 1 %) eugenol(21.1-56.7'/.)
lrans-o,-bergamotene T-cadinol(0.1-O.7%)
The occurrence of cedrol in this oil is doubtful. It reouires (0.5-9.7%)
unequivocalcorroborationbefore it canbe acceptedasteing t = trace (< 0.1%)
real.
AIso in 1990, Fun and Baerheim Svendsenused CC and This sameyear, Dixit and Shukla (1992) screenedan oil
GC/MS to analyze an oil produced from O. gratissimurL of O. gratissimu,m(eugenol-rich)againsta seriesof storage
erowing in the wild in Aruba. It was found to contain: fungi. From the results, the authors concluded that the oil
may prove to be an ideal storage {ungi-toxicant for the
tricyclene(t) eugenol(20.0%)
protection ofstored foodstuiTsin India.
o-pinene(0.5%) methyleugenol(0.5%)
(Z)-methylcinnamate(t)
Also in 1992, De Medici et al. reported the results of
B-pinene(0.3%)
camphene(0.4%) (E)-methylcinnamate(0.1%) the analysis of O. gratissimum oil produced from pi:rnt
sabin en e(0 .1% ) B-elemene (1O.4%) materialcollectedin Madagascar. The compoundsidentified
1-octen-3-ol (t) B-caryophyllene (39.8%) in the oil by capillary GC retention times and compound
my rce ne(0.1 % ) cr-humulene (2.9%)
co-iniection were as follows:
p-cymene(t) B-bisabolene (0.2%)
'1 (6.2%) y-cadinene(t) o-pinene(1.5%) c i t r o n e l l a( 1
l . 5 %)
,B-cinole
lim o ne ne(0 .1% ) 6-cadinene (t) B-pinene(0.5%) camphor(0.6%)
(t) (E)-nerolidol
(0.2%) myrcene(0.8%) linalool(0.2%)
7-terpinene
terpinolene (t) caryophyllene oxide(5.5%) o-terpinene (0.4%) linalylacetate(0.4%)
trans-sabinene hydrate(t) T-muurolol(t) 1,8-cineole(12.0%) B-caryophyl lene (2.7'/')
camphor(t) elemol(0.4%) y-terpinene(3.2%) o-terpineol (3.8%)
linalool(0.3%) T-cadinol(0.1%) p-cymene(0.2%) eugenol(40.3'/.)
terpinen-4-ol (t) o-cadinol(0.3%) terpinolene(0.2%)
borneol(1.0%) o-bisabolol(t) More recently,Pino et al. (1996)used GC and GC/MS to
: = tra ce (< 0 .1 %) analvzethe comoositionof the leaf and {lorveroils of a strain
of O. gratisslnruni grown in Cuba. Becausethe oils were
T\r'oyearslater, Larvrence(1992) reported the results of
qualitatively sirnilar,the range of composition for both oils
-r.eanalvsisof two chemotypesof O. gratissimum.The first
can be summarized as follor,vs,
rLemo\pe, which is rich in linalool, was found to contain
cx-thujene (2.21-8.23%) o-p-dimethylstyrene (0.70-1.19%)
I'e lbllowing components:
a-pinene (1.07-4.09o/o) terpinolene (0.24-0.30%)
r-plnene(0.2%) terpinolene(t) camphene(0.07-0.63%) linalool(0.21-0.70%)
; amph en e(0.1 % ) 1-octen-3-ol(0.1%) B-pinene(0.33-2.22%) borneol(0.55%)
:-pinene(0.3%) oxide (furanoid)
trans-linals1l myrcene(2.91-8.23%) terpinen-4-ol(3.24-4.35"/4
r:hi nana /A J o/^\ (0.3u a-phellandrene(0.07-0.21o/o) o-terpineol (0.53-0.55%)
-),,rcene(0.4%) camphor(1.2%) p-cymene(12.84-14.OO%) p-cymen-8-ol methylether
-onene (0.2%) linalool.(46.1%) (Z)-B-ocimene (0-0.21
%) ( 0 . 6 6 - .11 9 %)
: g-cineole(2.8%) oxide(furanoid)
cis-linaldbl (0.1%) limonene(2.90-5.27%) thymol(19.35-27.33%)
7 - R- nnim ana rfl 1ol^\ frans-u-begamotene (1.0%) ^y-terpinene(7.00-8.23%) carvacrol(2.19-3.09%)
-3-ocimene(1.2%) B-elemene (0.5%) frans-sabinene hydrate B-bourbonene (0.21-0.59%)
:-:ymen
- e(0.1 % ) B-caryophyllene(1.9%) (0.70-1.40o/.) B-elemene (O.24-0.557.)

t47

B-caryophyllene B-chamigrene (1.61-2.84%)
(7.23-11.50o/") y-cadinene(0.61-1.07%)
frans-B-bergamotene caryophylleneoxide
(1.03-2.29"/.) (1.74-3.02%)
cx-humulene (0.71-1
.36%) humuleneoxidell (0.10-0.52%)
B-selinene(4.35-7.960/")
Although these oils can be obtained in0.6-LGVo ields,
they have not achieved any economic importance because
they are examples of the thymol chemo$p e of O gr ati'ssimum'
oJ'
XJ. Yu and B-Q. Cheng. Analysisof thc chemicalconstituents
gratissimumaar. sio", ,til Yunnan Zhlwu Yanjiu, 8(2),
Or:itrum
171-174(1986).
V. A. Zan'rureenko,N. A. Kl1uev, L. B. Dmitriev, S G. Polakovaand
I. I. Grandbeig, Coo,pornnt compositionof-essential oils in
eugenol-typebisils.I'zv. TimiryazevskS-kh. Akad , (2) L72-175
(re86).
L. Ntezurubanza,J.I.C. Schefferand A. Baerheim Svendsen,
Conryosition of the essentialoil of Ocimum-gratissimunt grou;n
in Rroanda.Planta Med., 53,421-423 (1987).
R. K. Khanna.O. S.Sharma,M. L. Sharma,P N. MisraandA Singh,
Essential oil of clocimurrt. A 'strain of Ocimum C'q:ti:yy!
L. raised on alialine soils'Parfum. Kosmet.,69, 564-568( f 988)'
I. G. S. Maia. L. S. Ramos,A. I. R. Luz, M. L. da Silvaand M das
' G.r"o, B. Zoshbi. LJncommonBrazilian essentiol oils of the
Labiatae and iompttsitue.In: Flaaors ancl Fragrances:AWctrId
Perspectioe.trdits.',B. M. Lawrence' B. D. Mookerjee and B J'
Willis, pp. 177-188,trlsevierSci.Publ. B. V', Amsterdarn(1988)'
ential oil of A('aa aca,
O. Vostrowksy,W. Garbe and i. G. S. M aia,E s's
Ocimum gratissimamfrom Brazilian Amazon Ziet Naturforsch,
4 5 c , 1 0 7 3 - [ 0 7 6( 1 9 9 0 ) .
M -2. Wu, S-C. Xiao,W-J. Ren and P-Q. Chetl.,Chemical components
of the essentialoilfrom an escapeOcimttm gratissimum L uar'
SuaaeWlld. in Miyi County, Sichuan. Tianran Chanwu Yanjiu
Yu Kaifa,2(2),58-60(1990).
C. E. Fun and A. Baerheim Svendsen,Cottt'positionof the essentiul
oilsof OcimrLmbasilicum aar canum simsancl O. gratissimum L'
grou;nin Aru,ba.Flav.Fragr.J., 5, 173-177(1990).
B. M. Lawrence,Labiatae oils - mothernature's chemicalfactory'
In: Essential OiIs 1988-1991.Edit., B. M. Lawrence' pp l88-
2 0 6 , A l l u r e d P u b l . .C a r o l S t r e a r nI.L r 1 9 9 2 ) .
V. Dixit and K. Shukla, Et:aluation of essential oil of Ocimum
-283
fungi. In&an Perfum., 36, 277
gratissimum against.str,trage
(1ee2).
D. De Medici, S. Pieretti, G. Salvatore, M Nicoletti and P
Rasoanaivo, Chemical analqsis of medicinal plants bq gas
chromat csgr aphy and N MR spectro scoprJ Flav. Fragr' J'' 7, 275-
281(ree2).
A. Pino, A. RosadoandV. Fuentes,Compositionofthe essentialoil
'T. L grotun in
fromthe leaxesandJktuers of Ocimu'm gratissimurn
-Cuba.!.
Essent.Oil Res.,8, 139-14f (f996).
 Progress in Essential Oils
Reprinted
fromPerfumer
& Flavorist,
September/October No.S, p. 71
1gg7,Vol.22,

RosemaryOil 25 meter, 6-methyl-2,3-di-O-pentyl-y-cyclodextrincolumn

In 1987, Cartoni et al. used two capillary columns or a 2,3-di-O-pentyl-y-cyclodextrincapillary column, the
coupled in the following way: SE-54-Carbowax20M, and a monoterpene hydrocarbon fraction was determined to be:
temperature program of 60"C (5 min), 60"-80oC (2.C/min) (+)-0-thujene (0.30%) (+)-o-phellandrene(4.08%)
and 80"-170"C (4'Clmin) to resolvethe following rosemary (-)-cr-thujene(0.59%) a-terpinene (2.15%)
o i l cons t it uent s : (-)-o,-pinene(12.35%) p-cymene(1.69%)
o-pinene (+)-cx-pi
nene (17 .14o/o) (-)-B-phellandrene(0.15%)
campnor
camphene terpinen-4-ol (-)-camphene (16.71o/o) (+)-B-phellandrene(5.85%)
(+)-camphene(3.34%) (-)-limonene(5.7Bo/o)
B-pinene borneol
myrcene or-terpineol (-)-B-pinene(11.25o/") (+)-limonene(3.14o/o)
ttmonene (+)-B-pinene(2.08%) y-terpinene(4.57%)
bornylacetate
1,8-cineole myrcene(8.11%) terpinolene(2.08%)
B-caryophyllene
y-terpinene B-bisabolene
linalool The authors were also able to determine that the OII .l

fraction did not contain any (*)- or (-)-6-3-carene or any

Although the authors did not present any quantitative data,
(-)-o-phellandrene.
the relative amountsof eachconstituent could be estimated
The following year, Ravid et al. (1993) found that the
from the chromatogrampresented.
enantiomeric distribution of camphor in rosemary oil was
Two years later, Mookherjee et al. (19S9)compared the
( R)-( + ) -camphor (667o): (S)-(-) -camphor (S4Vo)
.
dlnamic headspaceanalysesof living and harvested rose-
Piccagliaet al. (1993) examined ,or"-"ry oll with the
nary with the direct GC/MS analysisof a commercial rose- "
iollowing major r.omponents:
mary oil. The comparative chemical compositions can be
seenin Table L ct-pinene(9-30%) 1,8-cineole
(14-50%)
borneol(1-8%) camphor(7-22%)
Table l. Comparative chemical composition (o/o) The oil exhibited no growth against a series of 25 different
from headspace analysis of living and harvested bacterial strains. In addition, this same oil exhibited only
rosemary and from GC/MSanalysis of rosemary oil
very low antioxidant activity.
A year later, Spiro and Chen (1994)examinedthe kinetics
Living Harvested
Compound plant plant
of rosemary leaf extraction using hexane,ethanol and two
Oil
hexane/methanol mixtures(10.1:S9.9and 8g.7:10.3)over a
(E)-2-hexenal o .2 temperature range of 25o_45"C. They concluded that the
(Z)-3-hexenol 0 .7
hexanal mixed solventscomplemented each other. The dehydrating
0 .3
c-pinene o .7 1 3 .3 effect ofethanol altered the surfacetension ofthe essential
myrcene
oil gland wall causing it to rupture more readily, thereby
9 .5 11. 1
B-pinene 0 .2 0. 1 7.6
acceleratingthe dissolution rate of the cuticular layers by
p-cymene 1 9 .8 13.7 1a hexane,resulting in a more rapid extraction.
ilmonene 14.1 | +.o 1 .0 In 1995, Perez-Alonsoet al. used a combination of GC,
1, 8-cin eo le 2"0 0.7 44.5 GC/MS, IH-NMR and 13C-NMRto examinethe comnosi-
linalool aa
7 .6 0 .8 tion of rosemary oil produced {rom Rosmarinu.sofficiialis
camphor - 1 0.1 grown in Turkey. In this analysis,the authors characterized
methylchavicol 3 .0 0 .3 t the following constituents:
cls-carveol 0 .2 0 .6 cx,{hujene
(0.35%) 1,8-cineole (36.91%)
citronellol 0 .6 1 .1
a-pinene(0.44%) o-terpinene(1.52%)
cr-campholenic
alcohol+
camphene(3.81%) cis-sabinenehydrate(1.93%)
o-campholenylacetate 0 .3 0 .8 sabinene(0.44%) camphor(7.63%)
t = t ra c e( < 0 . 1 % ) B-pinene(0.44%) frans-sabinene hydrate(1.44%)
myrcene(0.38%) borneol(17.50%)
o-phellandrene(0.38%) terpinen-4-ol (3.63%)
In 1992,Kciniget al. determined the enantiomerspresent
crterpinene(3.29%) o-terpineol(0.e3%)
in a monoterpene hydrocarbon fraction of rosemary oil p-cymene(10.50%) trans-piperitol(0.38%)
produced in Germany.Using chiral GC analysison either a limonene(0.82%\ cls-piperitol(0.54%)
 bornylformate(0.32%) carvacrol(1-73o/") camphor(27.3'/") caNailol (0.2Y")
piperitone
(O-76%) B-caryophyllene (1.22%) borneol(9.0%) B-caryophyllene(1.7%)
bornylacetate(1.64'/.) cr-humulene (O.25%) terpinen-4-ol(1.6%) cr-humulene (0.8%)
thymol(0.90%) oterpineol (3.8%) caryophyllene oxide(0.2%)
verbenone(6.3%) y-eudesmol(0.3%)
Although o-terpineol wasonly a minor constituent( 1.27o) bornylacetate(1.4%)
of an Israeli-produced rosemary oil, Ravid et al. (1995)
determined that it existed in the following enantiomeric A sample of rosemary oil that was produced in China
ratio:(4R)-(+ )-a-terpineol(697o) :(aS)-(-)-a-terpineol(377o). was determined (Zhu et al., 1995) to contain the following
This same year, Domokos et al. (1995) found that comnonents:
samplesof Hungarian rosemaryoil contained the following o-pinene(8.53%) camphor(7.25%)
componenrs: camphene(2.21%) borneol(1.71'/.)
(4.1-14.4'/.)
cx,-pinene camphor(13.0-31 .0%) B-pinene(3.66%) terpinen-4-ol(0.28%)
borneol(1.0-3.55%) myrcene(0.39'/") (1.35%)
o(-terpineol
camphene(4.0-4.4%)
verbenone(2.5-11.0%) p-cymene(1.00%) bornylacetate(0.83%)
B-pinene(5.3-13.7%)
bornylacetate(1.1-3.5%) 1,8-cineole (69.33%) B-caryophyllene (1.69%)
3-octanone(t-10.0'l.)
p-cymene(0.3-1.8%) (1.1-3.3%) linalool(0.33%) o-caryophyllene-.(0.18%)
B-caryophyllene
1,8-cineole (23.1-46.4'/") .. The authors probably meant s-humulene not u-caryophyllene,which is an
unacceptablename.

Tomi et al. (1995) used both GC and CC/MS to examine In 1996, Mul6 et al. determined that rosemary plants
an oil produced from R. offi cin ali s collected in the mountain- obtainedfrom avarietyof sources(suchasFrance, Morocco,
ous region ofAndalucia, an areathat is consideredto receive Spain and Italy) had an oil yield of 0.30-0.707o,while plants
the highest rainfall (> 100 cm) in Spain.The oil was found to grown under the same conditions in Sardinia had an oil
possessthe following composition: yield range of 0.50-I.50Vo.The authors determined that the
camphor(32.33%)
oils contained:
a-pinene(11.5%)
camphene(4.63%) linalool(1.62%) tx-prnene p-cymene
p-pinene(1.60%) bornylacetate(1.36%) campnene linalool
myrcene(6.52%) B-caryophyllen e (0.57%) B-pinene bornylacetate
limonene(3.45'/') cxterpineol (1.51%) o,-phellandrene camphor
(14.41%)
1,8-cineole borneol(1.55%) myrcene B-caryophyllene
(0.71%)
T-terpinene verbenone(5.30%) limonene borneol
3-octanone(6.15%) geraniol(t) 1,8-cineole verDenone
p-cymene(1.42%) T-terpinene geraniol
t = trace (< 0.01%)
Although they did not present any quantitative data, they
r3C- reported that the Sardinian oil-while containing relatively
Also in 1995, Tomi et al. used comPuter-assisted
NMR analysisin combination with capillary GC analysisto moderate amountsof monoterpeneestersand verbenone-
determine that a lab-prepared Corsican rosemary oil was rich in monoterpene hydrocarbons.thereby giving it a
contained the following components: good fragrance.
cr-pinene(22.O%) p-cymene(1.2%) Also in 1996, Ravid et al. examined the enantiomeric
camphene(6.3%) c am phor( 11. 8% ) distribution of borneol in ten samplesof lab-distilled rose-
B-pinene(3.9%) linalool(3.4%) mary oil. As can be seen from the summary of their results
myrcene(3.4%) bornylacetate(8.7%) given in Table II, the enantiomeric distribution of borneol
o -ph ella nd ren(1.
e 3% ) terpinen-4-ol (1.1%)
pinocarveol.(0.9%)
differs depending upon the rosemary cultivar. The authors
clterpinene(0.7%)
limo ne ne(3.1 % ) a-terpineol (1.0%)
B-phellandrene (3.0%) borneol(3.2%) Table ll. Enantiomericdistribution of borneol
1,8-cineole (3.0%) verbenone(10.7%) in cultivars of rosemary
(Z)-B-ocimene (1.2%) geraniol(0.5%)
yterpinene(1.9olo)
Cultivar Borneol(%) (1R)-(+)-Borneol (1S)(-)-Borneol
"correct isomer not identified 45
lsrael1 8.4 55
lsrael2 5.9 26 74
This was a good example of the value of this anallical
Greece 6.2 43 57
technique becausethe analysiswas reasonablydetailed. 67
Spain 9.4 33
Using GC/MS, Bourrel et al. (1$95) analyzedan oil of
"Mojorica" 0.8 4 96
rosemary that was screenedfor its antimicrobial activity' The
"Corsican" 2.6 83 17
oil was found to confain: "Tuscanblue" 11.2 5 95
o,-pinene(4.4%) 6-3aprene (0.5%) "Sevensea" 1.2 16 84
camphene(2.8%) p-cyinene(1.B%)
(22.2%) "Frimleyblue" 1.3 83 17
sabinene( 1.0%) 1,8-cineole
y-terpinene (10.8%) "Postrate" 6.1 62 27
B-pinene(0.3%)
a-phellandrene(3.2%) linalool( 1. 3% )

150
pointed out that because of this wide variation in enantiomer Gi nger Oi l
ratios, there was probably a genetic variation in R. fficinalis.
In 1994, Koenig et al. examinedthe enantiomeric distribu-
As a result, the enantiomeric distribution of borneol cannot
tion of two s"rqnit"rp"ne hydrocarbonsin ginger oil. Using
be used to identify the addition of non-natural sources of
chiral GC analysisthey found that (+)-ar-curcumene and
borneol in commercial oils. (-)-F-bisabolenewere the predominant forms of these two
sesquitelpenehydrocarbons.
G. P. Cartoni, G. Goretti and M. V. Russo,Capillary columns in
series for the fast chromatographic analysis of essential oils.
Also in 1994, Bartley and Foley analyzedthe chemical
Chromatographia,23, 790-795(19S7). composition of a supeicritical fluid extiact of Australian-
B. D. Mookherjee,R. A. Wilson, R. W. Trenkie, M. J. Zampino and grown ginger. The freshly harvested roots were peeled and
K. P. Sands,Neu dimensionsinJlaaorresearch. Herbs aidspices. chopped into 2 mm cubes before grinding under liquid
In: Flaoor chemistnl trendsand deaelopments.F,dits.,
R. Teranishi, nitrogen. The pulp was mixed with coarsegranulatedCelite
R. G. Buttery and F. Shahidi, p. 176-187,ACS S1.mp.Series, (diatomaceous earth) and subjected to extraction by
Amer. Chem. Soc.,Washington,DC (1989).
supercriticalCO' The analysiswasperformed by a combina-
W. A. Konig, A. Kriiger, D. Icheln and T. Runge, Enantiomeric tion of capillary GC (for retention indices and quantitative
composi,tion of the chiral constituents in essential oils. Part I.
Monoterpene'hydrocarbons.J. High Resol. Chromatogr., 15,
data) and GC/MS (for component identification confirma-
184-189(1992). tion r. Jls compoundsideniifiedwere:
U. Ravid, E. Putievsly and I. Katzir, Determination of the hexanal (O.52o/o) (0.189"/
B-farnesene*
enantiomeric comltosition of (1R)-(+) ond (1sl(-)-camphor in 3-methylhexanol(0.11%) ar-curcumene(9.25%)
es,sentialoils of some Lamiaceae and Compositae herbs. FIav. o,thujene(0.93%) zingiberene (2S.B7o/o)
Fragr.J., 8,225-228(1993). camphene (3.71o/o) s-bisabolene. (10.83%)
R. Piccaglia,M. Marotti, E. Giovanelli,S.G. DeansandE.Eaglesham, B-pinene (0.08%) B-bisabolene (2.739o1
Antib acterial and antioxidant prop er-ties of Med ite rra nea n myrcene (0.53%) y-cadinene(0.14%)
aromatic plants. Indtst Crops Products,(2), 47-50 ( f 993). limonene (0.430/") B-sesquipheltandrene (8.18%)
M. Spiro and S. S. Chen, Kine tic s of soloent extraction of essential oil B-phellandrene (1.63%) etemol(0.25%)
1,8-cineole (2.99o/o) dodecatrienol"(0.22%)
fromrosemary learses.FIav. Fragr. J., 9, f87-200 (f994).
linalool(0.46%) o-bisabolol(0.14./.)
M. J. Perez-Alonso,A. Velasco-Negueruela,M. Emin Duru, M. borneol(0.60%) cls-sesquisabinenehydrate
Harmandasand j.L. trsteban.Cotnpositionof the essentialoilsof decanal (0.11%) (0.22%)
Ocimam basilicum aar. glabratum and Rosmarinus fficinalis neral(2.87o/o) zingiberenol(0.15%)
fromTurkey. J. Essent.Oil. Res., 7,73-75 (1995). geraniol (0.66%) aromadendrenol" (0.20%)
U. Ravid. E. Putievsly and I. Katzir, Determination of the geranial(25.06%) zongerone (0.64%)
enantiomeric composition oJ'a-terpineol in essential oils. Flav. isobornyl acetate(0.10%) pentenyl
curcumene* (0.20%)
Fragr.J., 10,281-284(1995). geranylacetate(0.12%) (0.08%)
G-paradol
8-elemene (0.23%) 6-shogaot(0.31%)
J. Domokos, tr. Hethelp, J. Palinkas,S. Szirmaland M. Heltmann-
Trlok,Rosemary essentialoil of Hungarian origin. OIaj Szappan B-elemene (0.20%)
Kozmet.,44(3), 102-r05 (1995). * correctisomernot identified
P. tr. Tomi, P. L. Cioni, G. Flamini and A. Stefani,Eoaluation of
the chemical composition of the essential oils of some Larniaceae The following year,Tomi et al. (1995) used a compurer-
from Serraniafu Ronda (Andalucia, Spain).1.Essent.Oil Res., assisted13C-NMRanalysisin combinationwith capillaryGC
7,279-282 (L995). analysisto determine that the major componentsof ginger
F. Tomi, P. Bradesi,A. Bigelli and j. Casanova,Computer-aided oil were:
identification of indiuidual components of essential oils using
camphene(7.9%) B-bisabolene(5.9%)
carbon"-NMR spectroscopy.J. Magnet. Reson. Anal., 25-34
(1ee5). limonene(6.0%) (E,E)-cr{arnese
ne (5.4%)
zingiberene
(27.2%)
C. Bourrel, G. Vilarem, G. Michel and A. Gaste,Et ud e despropridtds
bacteriostatiques et fongistatiques en milieu solide de 21 huile,s That same year,Zhu et al. (1995) reported that Chinese
essentielles prdamblementanalysdes.Rivista Ital. EPPOS, (f6), ginger oil possessed the following composition
3- 12 (1 99 5).
L-F. Zhu, Y-H. Li, B-L. Li, B-Y. Lu and W-L. Zhang, Aromatic 5-methyl-2-hexanol(0.10%) cxterpineol (0.37%)
plants and essential constituents. Supplement 'l, p. 160. South a-pinene(1.04o/") citronellol(0.21o/o)
China Institute Botany,ChineseAcad. Sciences,Hai Feng Publ. camphene(3.88%) neral(1.34k)
Co., PeaceBook Co., Hong Kong (1995). B-pinene(0.14%) geraniol(0.30%)
6-methyl-5-hepten-2-one geranial(2.93%)
-\. Mul6, D. L. Moretti, G. Pirisino and M. Salta,Studio dellaresae (0-37'/") bornylacetate(0.23./")
della composizioine chimica dell'olio essryziale di Rosmarinu,s myrcene(0J2%) 2-undecanone(0.21%)
officinalis L. spontaneo cli cala gonone (Sardegna). Rivista Ital. p-cymene(0.13%) 8-elemene(0.10olo)
EPPOS,(19), 147-157(1996). 1,8-cineole(4.00o/o) citronellylacetate(0.29%)
U. Ravid, E. Putievsly and I. Katzir, Sqereochemicalanalysis of heptylacetate(0.10%) geranylacetate(2.92'/.)
borneol in essential'oilsusingpermethllaterl pctlclofuxtrin as a linalool(0.46%) o-elemene(0.81%)
chiral stationary phase.Flav. Fragr. I., 1f, 191-195(1996). camphor(0.10%) zingiberene (0.28%)
borneol(0.48%) B-caryophyllene (O.aa%)
terpinen-4-ol(0.10%) B-gurjunene (0.58%)
 ar-curcumene(26.31%) B-bisabolene (13.49%) 3,7-dimethyl-(32,62)- 2-(2',3'-epoxy-3'-methylbutyl)-
(3.39%)
cx,-cedrene nerolidol"(0.92%) octadienal 3-methylfuran
y-cadinene(4.51o/") camphenehydrate 3,7-dimethyl-(3E,6E)-octadienal
isoborneol

More recently,Vahirua-Lechatet al. (1996) analyzedan

AIso in 1995, Nishimura made a hexaneextract of fresh
oil of ginger produced from rhizomes harvested in Tahiti
gingerwhich he subjectedto analysisusing silicagel column
during a 2-year period. Using GC/MS as the method of
chromatography to yield a hexane-eluted fraction and
analysis,the authors identified the {bllowing components:
a methylene chloride-eluted fraction. Each fraction was
further subjected to gas chromatographic separationon a 2-heptanol(0.23-0.29%) geranial(8.89-1 8.10%)
wide-bore, thick-film polar capillary column (30 m x 0.53 o,-pinene (1.80-2.'|9%) citronellylacetate(0.24-0.27 %)
mm, film thickness 1.0 pm). The GC was fitted with a camphene(5.63-6.48%) d,-copaene(0.26-0.33%)
thermal conductivity detector and a glass sniffing port to B-pinene(0.38-0.75%) (E)-B{arnesene (0.31-0.35%)
myrcene+ s-octanol ar-curcumene (0.40-3.55%)
which moist air was pumped at a flow rate of 100 ml/min.
(1.23-1.26%) zingiberene + (E,E)-o,{arnesene
After determining that the orygenated (or methylene chlo- (5.09-8.69%) (3.32-7.83%)
B-phellandrene
ride) fraction was richest in odor, the researchersanalyzedit 1,8-cineole(2.1B-4.03o/") B-bisabolene (7.92-8.77 %)
by rnultidimensional GC/MS (MDGC/MS). In addition, linalool(0.81-0.88%) B-sesquiphellandrene
some componentswere ideniified by IR and NMR analysis citronellal(0.11-0.37%) (7.14-7.98%)
borneol(1.29-1.34%) germacreneD (0.24-0.56%)
once they had been isolatedby preparativeGC. In combina-
terpinen'4-ol (0.15-0.53%) viridiflorol(0.47-0.72%)
tion r,viththis, the orygenated fraction was analyzed accord- cx-terpineol(0.81%) y-eudesmol (0.33-0.79%)
ing to the procedure known asaroma extract dilution analysis citronellol(0.85-1.02%) cr-cadinol (0.57-O.7 3%)
(AEDA) (Grosch 1994),with the resultsbeing expressedas neral(5.37-6.69%) B-eudesmol (0.17-0.60%)
flavor dilution factors (FD). FD is the ratio of concentration geraniol(0.60-1.82%) B-sesquiphellandral (0.12-0.45%)
in the oure extract to its concentrationat the lowest level of
detection, or the most dilute extractwithin which the com- It should be noted that it is highly unusual to find a

ponent can be detected. Consequently,the higher the FD ginger oll with such high levels of orygenated constituents
value, the more important is a component'scontribution to and such correspondingly low levels of sesquiterpene
hydrocarbons.
the overallaromaof the extractwithin which it is found. Also,
it is generallyaccepted(Grosch 1994)that componentswith
W. Grosch, Determination of potent odorants in foocls by arorna
FD values greater than 10 are the main contributors to the
extract difution analysis (AEDA) ancl,calculation of odor actitity
odor of the oil or, in this case,the orygenatedfiactlon of the xalues(COAYS) Flav. Fragr. J., 9, 147-15E(1994)
extract.The comooundsthat were found to have FD factors W. A. Koenig, A. Rleck, I. Hardt, B. Gehreke,K-H. Kubeczkaand
greater than 10 are listed here along with their FD factors: H. Muhle, Enantiomeric contpo,sitionof the chiral constitLtents
of essential oils. Paft 2. Sesquiterpene hydrocarbons. J. High
1,B-cineole (15) ner al( 15)
Resol.Chromatogr.,17, 315-320(1994).
bornylmethylether(11) bor neol( 16)
2-heptanol(13) geranial(17) J. P. Bartleyand P. Foley, SupercriticalJhid extraction of Au,straliart-
(E)-2-octenal (12) geranylacetate(14) grou;n ginger (Zingiber fficinale). l. Sci. Food Agric., 66, 365-
citronellal(11) ner ol( 10) 371 (1994).
de ca na(1
l 1) geraniol(20) F. Tomi, P. Bradesi,A. Bighelli and J. Casanova,Comlruter-aided
linalool(20) zingiberenol (1 1) ifuntification of indnidual conponertt.s of essential oils usirtg
2-undecanone (14) (E)-2-dodecenal (11) carbonr']-NMR spectroscoplJ.J. Magnet. Resol. Anal., 25-34
(E)-2-decenal (11) isoeugenol- (13) (1ee5).
citronellylacetate(16) L-F. Zhu, Y-H. Li, B-L. Li, B-Y. Lu and W-L. Zhang, Arornatic
plants and es,sentialconstituents. StLpplement-1, p. 68, South
China Institute Botany,ChineseAcad. Sciences,Hai Feng Publ.
From these results, it can be concluded that l,8-cineole, Co., PeaceBook Co., Hong Kong (1995).
linalool, citronellyl acetate,borneol, geranial and geraniol O. Nishimura, Iclentification of the characteristic oclorants infresh
are the most important contributors to the odor of fresh rlilzonrcs of ginger (Zingiber fficinale Roscoe) using aromrL
ginger. extract dihttion analysi,s and nutdified nrultidimensional gos
chromatographq-mass spectrometry.J. Agric. Food Chem., 43,
Using MDGC/MS, Nishimura alsoidentified some other
2941-2945(1995).
constituentsin this fresh ginger extract,although he did not
I. Vahirua-Lechat,C. Menut, G. LarnafandJ. M. Bessiere,Huiles
present any quantitative data. The additional compounds essentiellesde PolyndsieFranEais.Rivista Ital. EPPOS, (Numero
i d ent iliedwer e: Speciale),627-638(1996).
2_octanol nonanal
2,6-dimethyl-5-heptenal 2-pine1-S-ol. SchinusmoileOal
2-nonan6ne c/s-roseOXIOe
trans-rose
oxide During an initial analysis of the fruit oil of Schinus mctlle
2-(3'-methyl-2'-butenyl)-3-
2-octylacetate L., Terhune et al. (1974) used a combination of modern
methylfuran
 spectroscopictechniquesto_identifya sesquitelpene
hydro_ cr-plnene(2.66%) 0(-muurotene(1.4Bo/")
carbon in a reduction product of spathulenol which B-pinene(0.17%)
they D-cadinene (9.11o/o)
named B-spathulene. myrcene(20.41'/")
B-guaiene(0.22%)
The followingyear, cx-phellandrene(12 .34%) cafamenene"(02A%)
Jenningsand Bernhard (1g75)charac_ limonene(7.25%)
terized the following components in a lab_distilled geranylbuiyrate(0.94o/o)
oil of B-phellandrene (6.21%)
S. molle: T-calacorene (O.15%)
p-cymene(2.99o/") d-calacorene(0.26%)
c[-ptnene terpinolene terpinolene(O.10%) elemol(1.32%)
campnene methyloctanoate methyloctanoate(0.95%) neryl hexanoate (0.28o/o)
B-pinene B-bourbonene o-cubebene(0.19%) y-eudesmol(1.04%)
sabinene frans-c[-bergamotene o-copaene(0.12%) T-cadinol(1.39%)
myrcene cr-gurjunene(0.71%)
B-caryophyllene T-muurolol(2.32%)
o-phellandrene tx-terpineol B-elemene(0.52./") o,-muurolol (0.69%)
d,-terptnene germacreneD B-caryophyilene (2.02%) o-eudesmol(0.90%)
p-cymene 6-cadinene s-humulene(0.58%)
B-eudesmol (1.O1o/")
T-muurotene (0.48%) cr-cadinol(6.64%)
Un{brtunately the authors did not present any quantrtative
data, although the compo,lrrd, *"ri identifieh bv u * correct
isomer not identified
nation of retention indices and GC/MS. "o*bi_
The following year, Lawrence (1gg4) examined
Eight years later, Bernhard et al. (lgg3) analyzedan the
^ oil composition of three lab-distilled fruit oils of
ol S. molle lruit produced th" Likens-Nickerson appara_ S. molle,
!y produced from fruits harvested in California and Florida,
tus using GC/MS. They found that the oil contained
the using a combination of modern analytical techniques.
following components: As
can be seenin Table III, the compositionof the oils
showed

Tabfe lfl. comparative chemical composition (o/o)

or schinus moile oils
Compound 1 2 3 Compound 1 2 3
o-thujene 0.2 0 .2 I phellandral 0.5
ct-ptnene 3 .1 0.1 I
2 .7 1.4 carvotanacetone
campnene 0.2 I I
0 .1 LZ I germacreneD
B-pinene I 2.4 o.2
0 .1 0.4 0.2 bicyclosesquiphellandrene
sabinene 0.3 t 0. 9
I I 0.2 ptpentone 0.6 0.1
6-3-carene t 0. 2
I 0.1 Y-elemene+ t
myrcene 1 1 .6 5 .0
I 0.2
1 9 .0 geranylacetate 0.1
o-phellandrene 12.7 0.2 0. 1
9 .1 6-cadinene 4"7
s-terpinene 2 .1 6.8
I I
limonene Y-Cadtnene 0.1 0.1 0. 3
9 .0 8. 4 8.3 p-mentha-1,3-dien-7-al
B-phellandrene 0.2 0.5 0. 1
7.2 4. 8 6 .3 o(-cadinene
y-terpinene 3.8 2.2 1. 1
0.8 I 0.1 trans-p-mentha-1(7),5_dien_2_ol 0.4
p-cymene 1 0 .5 0.7 0. 5
11. 5 6.2 calamenene*
terpinolene 0.2 0.3 0.3
0 .6 0. 1 0 .1 Y-Catacorene
methyloctanoate 0.1 0.1 0.1
0 .2 1. 2 t.o palustrol
methylnonanoate 0.5 0.1 I
t I I caryophylleneoxide
c[-cubeoene t I I
t 0 .2 0 .2 epi-cubenol
0-copaene 0" 6 0.6 0. 5
t 0 .4 0 .6 0-calacorene
0-gurJunene 0.1 I 0. 1
1 .0 0 .3 0.6 0,-coracalene
linalool 0.1 t I
0 .1 0 .3 0.8 cubenol
c/s-p-menth-2-en- 1-ol 0.6 2.4 0. 3
I 0 .1 0 .1 elemol 0.2
bornylacetate 0 .1 1.0 1. 0
0.2 0 .1 spathulenol 2.5
B-elemene 0 .1 3.6 2. 0
0 .3 0 .4 T-eudesmol
terpinen-4-ol 0.1 0.2 1. 0
1 .3 0.5 o.4 T-cadinol
B-caryophyllene 2.5 2.0 0. 7
0.3 LZ T-muurolol 2.2
trans-p-menth-2-en- 1-ol 0 .2 1.4 0.2
0 .1 I o,-muurolol 0.5
cryptone 0 .2 1.0 1. 1
I I carvacrol
s-humulene 1.0 1.0 0. 6
3 .0 0 .7 0 .8 0,-eudesmol
y-muurotene 0.2 0.7 1
0 .1 0 .9 t B-eudesmol
d-terpineol 0.4 0.3 I
0 .3 i?.0 0 .2 viridiflorol
p-spathulene 0 .3
o. l 5.8 6. 5
_ 0 .1 0 .1 cr-cadinol 0.2 0.2 0. 3
cadina-1 (6),4-diene t 1 t cadalene
viridiflorene 0.5 I 0. 1
0 .3 . 0 .8 I guaiazulene
cr-muurolene 0 .5 - 0 .1 I t t
I
t = t rac e( < 0 . - 1 % ) ; - c o r r e c tiso !n :| n o lid e n tifie d ;+ p
'1= oil produced
from ripe californianfruit;2 = oil pl'ooucecitrom driedcaliforniantrul; i1-oir proorcedfrom dried Floridian
truit
 cr-terpineol (1.25'/") 8-cadinene (1'26%)
no qualitative
only minor quantitative variations and g"rtu.r"nt D (12.08%) caryophyllene oxide(0'53%)
germacrone (0'75%)
variations. 6i"y"tog"tt".rene(29.20%)
of
In 1987,Devalle G, and Schwenkeruseda combination : a nerD
t"- and i3C- S.J.Terhune,J.W. Ho-gg andB M Lawrence' ft spathulene
,rll"" g"l chromatography,HPLC' Yt' ntolle oil Phyochemistry'13' 865-866
' sirquit"r't)Jneitt Scititrus
"ol.tmn -prJsenceof preisocalamenediol
NMR to characterizethe ( 1974).
in an acetoneextract of S' molle leaves' andR.A. Bernhard' ntponenls oJ
I tlcnI ifit'uI ittn'[1'.o
W. G. Iennings
(1990)used CC/MS ( nlotIc L'
tt i"uloi I of t h e CaI ifort ti a n pt 1tper I reP 5cI It n u
s
Three yearslater, Maffei and Chialva t h e esset
of oils produced 95-96 (1975)
,o the chemical composition Ctt"*. UlLtoUiol. technol Lebensmitt ' 4'
The
"o-pit"leavesand berries (fruitJ of S' molle collectedfrom T. Shibamoto,K' Yamaguchiand E White'
from thf -'' A. Bernhard,
R.
Ll Food Chem' 3 l'
(ttaly)'. Th-e-components uototiiol entsof S chiruts mott e J'Agric
naturalized plants in Liguria "irstitu
oils are listed in Table IV' 463-466(1983).
identifiecl in ihe two molle and Schinu's
B. M. Lawrence, A cliscussiono/ Schinrr'r
Flavor', 9t5)' 65-69 (f984)'
inrrbtrthfoliu,s. Perfum
(%) Prei'socrtlomenecliol' a
Table
'-? lV. Comparative chemical composition " l,t.
D. pevalle G. and G Schwenket'
in" teat hno berry oils ot Schinus molle ;;"t;;";;;,r1S"hrrut mnlle PIatta Med'' 230 (1987)'
molle berries
M. Maffei and F. Chialva, Essentialoilsfrom .schinr;,l
BerrY oil ant!IeaucsFlav. Fragr'J" 5' 49-52 f 1990)
Compound Leaf oil
s
C. Rossini, P. l'1 tr D ellacassaand P' Moyra' EssantirLloil
1. 46 3.96 "'-itoiinou:,nt "r."r.,le,,' of Urugtayart
cr-pinene
oo5 of Schinusmolle and S' Ientiscfolitts
camPhene t 'orisin' Essent.Oil Res , 8, 7f-73 (f996)
0.19 T.
B-pinene
0.10
0.67 0.45
sabinene
Santolina Oil
myrcene 1i their
o-phellandrene 30.24 55.42 In 1992, Schmauset al' and Brunke et al' republished
1992 (Lawrence
o-terplnene o.o2 0.03 results from earlier studiesthat I reviewed in
9.27 14.25
limonene 19e2).
p-phellandrene 9. 63 15"39 That same yeaq Perez-Alonsoand Velasco-Negueruela
p-cymene 0. 59 0 91 (l99ti the composition of oils.from four sub-
o.2o o'21 "o-pu.".l with oils producecl
terpinolene il;i;t of iantolina
r 2j 7 "ho*in"y7'oris,s indices as
methyloctanoate from three cultivars.Using GCTMSand retention
o'01 o 01 the authors
cr-cubebene their method of compoient identification'
o-02 o 01 of the oils' o.' t"" be seen fron'r
cr-copaene ;"-ili;J detailed
o .o 1 o 01 "ttoly'"' widely' The oils
B-elemene
0 .4 7 0.01 TableY the compositionsof theseoils varied
by Schmaus
B-caryoPhYllene
;i;;;"t" quite different from the oils examined
o.o3 o'04 $/ere;
terpinen-4-ol et al. and Brunke et al.' u'here the major components
y-elemene tI
0.39 I myrcene(3.60-9.61%)
cr-humulene
germacreneD 5 .2 1 0.13 (B'63-1
B-Phellandrene 7 93%)
o' 31 ketone(8.54-34
artemisia 10'i')
6-cadinene 1 .7 1
o'04 (9.10-17369')
longiverbenone
t
B-guaiene o' 04 of the li-ic1-
calamenene* 0 .9 3 It would seem that this is yet another example
13.25 o'72 can exist lvithln species in tl'=
elemol ranqe of chemotlpes that
2 94 o'23 Compositae familY.
neryl hexanoate
0.39 GC and GC
T-eudesmol
3.24
o'04 The following year, Giner et al' (1993)used
T-cadinol 4 70 of season andvegetative gro$ -:
t o' 10 MS to determini'the effect
T-muurolol the composition of the
stageof S. chamaecypartsus ''
t 0.08 -on
not use a tlpical artemrs '
cr-muurolol Altlough these a.tihors did
t 0.10 that :: '
c[-eudesmol
ketone-rich chemotlpe. their results showed
t 011
cr-cadinol
of th" o'iii, definite\ affected by the datc
"o*porition incon'rplt--
t = tru"u t.0.01%); " correctisomernot identified plani hawesting. A summary of this somewhat
data can be seenin Table VI'
t
the compo- ce,Sontolinaoil' In: Progressin Essettial
Morerecently,Rossiniet al'41996)examined B. M. Larryren
17(6), 53-56 (1992)'
f,orqthe and
ieaves twigsoI s' molle Perfum. Flavor,
rt,t;;;i;;ilpio,lrr""d elsr '-
The oil wasfound to contain: " Schmaus,
G. tr-J.BrunkeandF-J FT-"tt-:\*idt'The -
usingGC a risisL' RivistaItal trPPOS'(Nu:'
oiio,f5,,ui.,tiiachomttectlp
"rld^CCUNlS. (1y{erPinene "13%) 345-363 r 1992)'
B-pinene(13.95%) "' Specjol"'.
sabinene(12.92%) linalool(0.71%)
*tr-ft . Brunke, F-J. Han'rmerschmidt and G schmaus'l ' ' r
e (7.68'k) L Parfum Kosue: i i
myrcene(5.46%) B-caryoPhYllen
nrrniidti du iontono it"n*aectlparisu's
terpinen-4-ol(10.57%)
limonene(0.88%) 629-637 (1992).
(0.30%) cr-humulene (0'57%)
B-phellandrene

154
 Tabfe V. Comparative chemical composition (%) of various oils of Santotina chamaecyparisus

Compound 1 2 3 4 5 6 7
artemisiatriene 0 .1 t I 0.2 0.3 0.3 I 0.2 0 .1
ct-prnene 0 .1 0.2 I 1.0 1.1 2.7 0.3 0.2 0 .4
campnene 0 .2 0.5 I 1.0 3.0 8.0 0.1 0.5 1 .1
B-pinene+ sabinene o .2 o .7 0.1 1.3 1.1 0.8 0.6 2.O 5 .7
myrcene 0 .1 0.2 I 0.3 0.1 0.1 o.2 0.9 16 .1
yomogialcohol 0 .1 0.6 0.3 0.2 0.1 0.1 0.1 1.0 0 .4
p-cymene 1 .3 1 .4 0.8 t.o 1.1 0.2 0.9 0.4 0 .1
1,8-cineole 8 .7 2.3 6.0 17.6 0.3 2.9 2.8 13.2
artemisiaketone 0 .1 4 .5 2.8 1.5 1.2 0.1 0.1 27.8 25.6
terpinolene 0 .1 0 .3 0.2 0.4 0.3 0.3 0.2 0.3 1 .8
linalool 0 .2 0 .8 1.1 0.1 0.8 0.7 0.7 0.3 0. 1
B{erpineol- I I I 1.3 t I I ++

campnor 9.2 24.9 ' 18.9 22.5

I 42.9 8.3 2.0 4.7
isoborneol t.o 1. 7 LC t I 1.2 I tt
borneol I1 .6 12.8 26.0 11.3 28.4 8.4 2.3 0.9 0.6
terpinen-4-ol 3.1 4.4 c, l 1.0 z .+ 1.1 0.8
d-terpineol 1 .8 1. 9 z .z 1.3 2.0 0.5 2.7 0.3 0.2
y-terpineol 0 .5 3.9 0.6 t I I o.4 1.2 0.6
myrtenol 1 .7 i 1.9 0.6 t 2.4 I LI
dihydrocarveol 0.5 0 .5 0.3 0.2 I 0.7 t tt
verDenone o .4 0 .6 1.0 0.3 0.3 t 0.1 tt
carveol' 1 .0 0.7 1.1 0.1 t 0.2 0.1 t 0.1
myrtanol" 0.2 0 .1 0.3 iA t I 0.1 tt
linalylacetate 0 .1 0 .1 0.1 1 0.1 0.1 t 0.5 0.1
3,6,6-trimethyl
bicyclo[3,1,0]
hexane-3-carboxaldehyde 0 .1 I I I t 0.1 1.1 t I
h^r^r n ^^^+^+^
uvr rryr auErdlv 0 .1 0 .1 0.1 I 0.6 0.1 t t I
isobornylacetate 0 .4 0.4 0.7 0.1 I 0.1 I 0.1 0. 1
dihydrocarvylacetate 0.2 0.2 0 .1 t I 0.1 I 0. 1
nenr\rl 4^6+r+6* o .2 t 0 .1 I i 0.1 t 0. 1
yterpinyl acetatei 0 .1 0 .1 I I t 1 0.8 0. 1
allo-aromadend rene 0 .6 0 .5 0 .4 0.6 0.3 0.3 I 0.3 0. 2
ar-curcumene 1 .1 1 .0 0 .5 1.0 1.0 0.2 +.o 2.3 2.4
elemene*'** 0.5 o .2 t 0.7 0.3 0.2 0.5 0.5 0. 3
y-cadinene 0 .3 0 .4 0.2 I o.2 0.1 1.0 t t
6-cadinene 0 .9 0 .7 0.2 I.C 0.4 0.9 3.2 t.c 0. 4
elemol 0 .9 1 .3 1 5.0 I 2.1 z. l 2.5 no
nerolidol.+ spathalenol 8 .6 6 .8 7.7 9.3 3.0 0.7 6.1 3.7 1 .9
copaenol* | + .o 2 .7 5.8 15.2 t I 4.9 t.c o.4
ledol 5.2 2 .6 3.5 4.1 0.7 1.0 2.5 1.2 0. 7
cadinenol* I t I 1 I 0.3 I t.o 0. 5
caryophylla-4(12),8(13)-dien-5-ol
2.1 2 .3 1.8 t.o 2.7 0.7 10.2 I I
T-cadinol I i I 2.5 t I 6.0 23.6 4. 8
B-eudesmol 7. 5 4 .6 3.9 1.7 0.6 1.8 5.7 1.0 0. 8
o-cadinol 1. 7 0 .9 1 .0 2.4 0.4 t 1.4 3.0 0.9
cubenol t.o t.o o.t 0.4 17.3 12.9 1.7 8. 6
3B-hydroxymuurolene* 0 .6 t t 1.2 t 0.6 1.2 1.7 0.4
3B-hydroxy-5-cadinene I t I 1.9 0.1 i t 1.2 0.4
opropenone 0 .5 0.2 0 .2 I 0.6 t 1.1 I t
germacrone 0 .3 I 0 .3 ' 1.3 I 0.3 0.6 t.o 0.4
ct-bisabolol 0 .3 { * 1 .6 0.9 I 0.3 0.2 2.7 I o.4
B-bisabolol _ 0 .1 0.1 t 0.1 0.1
I t.o 0.8 1.1

3-oxo-T-muu
rolol 0 .1 0 .1 I 0.1 t t 1.7 o.4 0.1
* correctisomer
not identified;** incorrect basedon elutionorder;t = trace (< 0 .1" \; I compoundidentityis in question
Samples 1-3= S. chamaecyparisusssp.squarrosaiSample 4 = S. chamaecyparlsusssp.tomentosa;Sample 5 = S. chamaecyparisusssp.incana;
Sample 6 = S. chamaecypar.susssp. magonica;Samples 7-9: = S. chamaecyparisuscultivars
 Table Vl. Chemical composition (o/o)of santolina oil produced from plants harvested at different times

Date of Harvest

Compound Jan Mar May Jun Jul sep Nov

cr-ptnene 0.23 0.28 u. to
camphene I I 0.31 0.36 0.75
B-pinene+ sabinene 0.25 1.59 1.80 l. to
myrcene 0.19
cr-phellandrene
+ 6-3-carene 5. 66 5.00 0.31 0.18 1 .7 2
ctterpinene 0.65 0.20 0.36 0.53
limonene 0.59 0.28
B-phellandrene 0.16
p-cymene+ 1,8-cineole 4.07 2.43 5.80 0.72 0.31 9 .1 9
y-terpinene t.Jc 0.41
artemisiaketone 1. 39 o.27 2.49 0.30
terpinolene t.uc

cr-p-dimethylstyrene 3.02 2.14

fenchone 1.13
thujone- 0.15
cls-sabinenehydrate ,.oa 8. 9 1 1.48 0.18 0.22 6.54
campnor 4.98 3. 9 9 4.67 0.67 0.50 7.49
myrtenal 2.48 1.44 3.82 0.60 0.64 5 .7 1
borneol 7. 18 t.3 | 4.78 t.4 J 0.65 7.54
terpinen-4-ol 0.91
oterpineol 0.65
cuminaldehyde i.ro 1.83
bornylacetate+ isobornylacetate 10. 58 0.24 0.30 t.oc 1.31 5.79 1 .9 7
o-copaene 0.26 I 0.13 0.28 0 .1 1
c{,-yrangene 0. 1 4 o.29 I 0.31 0.33
allo-aromadendrene t. oo 0.35 0.91 i.oo 1.68 1 .3 2
o-cubebene 2.50 2.45 0.66 1.26 0.72 0 .5 1
B-gurjunene | .zJ 1.32 0.86 1.34 0.29
isocaryophyllene 0.69 t.uc 0.18 2.38 0.43 0.28
ar-curcumene 0. 5 9 2.39 0.22 4.83 0.32 0.23
cx-muurolene 0.98 . FA
0.21 I .JJ 0.26 0.60
germacreneB 2.7 9 2.58 0.73 z.J6 0.33 0.41
6-cadinene 0.49 0.41 U. IJ | .z o
unknownsesquialcohol1 15.67 3. 13 7.86 10.66 zv- tz 13.10 1 7 .1 9
unknownsesquialcohol2 2.43 J.O I 10.62 5 . 1B 8.16 z-63 4 .0 1
unknownsesquialcohol3 3.28 5.33 10.51 3.08 5.23 10.42 3.30
Total identified 43.44 33.43 13.01 46.62 24.40 15.91 4 7 .1 4
* correctisomernot identified;t = trace (< 0.01%)

\I. J. Perez-Alonso and A. Velasco-Negueruela, Essential oil 0-pinene(2.3%) benzylacetate(0.3%)

components of Santol,inachamaecyparisrzsL. Flav. Fragr. ]., 7, o,-phellandrene(5.1%) (E)-cinnamaldehyde (0.7%)
34-42 (L992). p-cymene(3.2ol.) eugenol(68.6%)
R. M. Giner, S. Manez and J. L. Rios, Seasonalaariations in the linalool(5.0%) (E)-cinnamylacelale(4.7ok)
essential oil of Santolina chamaecqparisusL. Sci. Pharm., 61, B-caryophyllene (0.7%) eugenylacetate(8.1%)
169-173(1993). oterpineol(0.4%) benzylbenzoate(1.0olo)

re Five years later, Variyar and Bandyopadhyay (1989)

Cinnamon Leaf oil reported that cinnamon leaf oil of Indian origln contained:
A {ew years ago, Yu et al. (f984) u-seda combination of
linalool(0.96%) (E)-cinnamyl
acetate(0.06%)
analyical GC, preparative GC and IR to examine the com- safrole(1.50%) eugenol(92.81%)
position of cinnamon leaf oil produced in Xishangbanna (E)-cinnamaldehyde (2.13olo) coumarin(0.06%)
(Yunnan,China). They found that the oil contained: (E)-cinnamyl alcohol(0.41%)
It should be noted that these authors used retention time
compositions, whereas an oil produced from leaves har_
data of authentic compounds on a packed GC column for
vested in the rainy seasonhad a reduced level of eugenol
component identification pu{poses.
and an increasedlevel ofeugenyl acetate(TableVIIIi
In 1993, Cheng and Yu reported that cinnamon leaf oil
Also in 1996,Nath et al. reported that the leaf oil obtained
produced in Yunnanpossesseda compositionthat varied as
from C. zeylanicum collected in the Brahmaputra Vallev
follows:
of northeastern India possessed .,."o**Jn chemical
cinnamaldehyde
(0.7-1.0%) "n
composition. The componentsidentified in this oil by GC/
eugenol
(79.1-82.6%) MS w ere as fol l ow s:
In 1995, Ravid et al. determined that the enantiomeric o-pinene(2.02%) ethyl benzoate(0.24%)
distribution of u-terpineol (L3qa) in a commercialsampleof camphene(1.24%) methylchavicol(0.69%)
cinnamon leaf oil was (4R)- ( + )-o-terpineol (205a): US)- e) _ B-pinene(1.77o/o) cinnamaldehyde (0.63%)
o-phellandrene(0.17o/") eugenol(0.69%)
u-terpineol (807o).
p-cymene(0.56%) methyleugenol (0.21"/")
Also in 1995, Mallavarapuet al. compared the chemical limonene(3.38%) lene (6.92ok)
B-caryophyl
compositionof cinnamon leaf oil produced in Bangaloreand 1,8-cineole (0.O4o/o) eugenylacetate(0.71%)
Hyderabad(India) using both GC and GC/MS. Their results l i n a l o o(l1 0 . 8 1 %) benzylbenzoate(65.42%)
are summarizedin Table VII. borneol(1.52o/")
More recently, the seasonalvariation in the composition This is an example of an unusual chemotl,pe that is not
of cinnamon leaf oil produced from leaves harvested at fbund in commerce. It is of interest to note that in the
different times of the year was studied by Kaul et al. (1996). germplasm of C. zeylanic:um brought to China from Sri
They found that oil produced from leavesharvestedeither in Lanka, Cheng and Yu (1991) had previously identified a
the summer or in the winter possessedcomparablechemical benzyl benzoate-rich cinnamon leaftil.

Table Vll. Chemicalcomposition (%) of cinnamon leaf oils from Bangaloreand Hyderabad

Compound Bangalore Hyderabad Compound Bangalore Hyderabad

a-thujene 0 .0 6 0.04 nerol 0.26
c-prnene 0.49 0.38 cuminaldehyde I
camphene 0 .1 7 0.1 8 piperitone
sabinene
0.03
t I (E)-cinnamaldehyde 0.63
0-pinene 0 .1 8 0.1 6 linalylacetate
myrcene
o.52
0 .1 3 0.09 safrole 0.19 I
oclanal I (E)-cinnamyl alcohol t
c-phellandrene 1 .0 3 0"50 2-phenethylpropionate I
6-3-carene 0.05 I eugenol 84.50 8 1 .4 3
c-terpinene 0 .0 3 t (E)-methyl
cinnamate i 1
p-cymene o.2B 0 . 16 (Z)-cinnamylacetate I I
1 ,8-cine ole 0 .3 8 0.23 B-elemene 0.28 0.25
p-phellandrene 1 1 (2,E)-cr{arnesene I
(Z)-B-ocimene I (E)-cinnamylacetate
(E)-ocimene
2.49 o.73
0.05 B-caryophyllene 2_25 0.47
7-terpinene 0.05 I (Z)-methylisoeugenol t
cls-linalooloxide (furanoid) t t s-humulene
frans-linalool
0.46 o. 12
oxide (furanoid) I I (E)-methyl
isoeugenol I I
terpinolene 0 .1 1 0.05 B-selinene t 1
linalool 3.70 eugenylacetate
t.Jl
0.14 2.85
2-phenethanol t y-cadinene 0.08 0.05
camphor 0 .10 ; caryophylleneoxide 0.11 0. 10
citronellal I 0.39 (E,E){arnesol t t
borneol 0. 12 t benzylbenzoate 0.13 8.29
terpinen-4-ol 0.04 0. 0 5 2-phenethylbenzoate
a-terpineol
I 0.08
0 .H 0. 1 0
methylchavicol 0 .1I I
(Z)-cinnamaldehyde t
\il
I
 X-j. Yu, X-R. Chen and B-Q. Cheng, Preliminary study on the
Table Vlll. Seasonalvariation in the chemical chemical constituentsfrom Cinnamomum zeylanicum Bl. Ieaaes.
composition (%) of cinnamon leaf oil Yunnan Zhiwu Yanjiu, 6(10), 103-f07 (1984).
P. S. Variyar and C. Bandyopadhyay, On some chemical aspectsof
Winter Summer Rainy Cinnamomum zeylanicum. PAFAI (OcVDec), 35-38 ( 198g ).
Compound oil oil season oil
B -Q. Cheng and X-J. Yu, lnrro du ced Ceylon cinn amnn cuhio ars and
d,-thujene 0.06 0.03 chemical coml:tonentsof their essential oils. Linchan Hauxue Yu
cr-prnene 0.59 0.33 0 .11 Gongye, 11, 325-332(1991).Cited in L-F. Zhu, D-S. Ding and
campnene 0 .3 3 0 .1 2 0.04 B. M. Lawrence,The Cinnamomann, speciesin China: resources
B-pinene 0 .2 0 0 .1 6 0.04 Jbr the p resent and future. Perfum. Flavor., lS (4), l7 -22 ( L994) .
myrcene 0 .0 9 0.05 B-Q. Cheng and X-J. Yr, Cultioation of Ceylon cinnamon ond
cx-phellandrene 0.59 0.23 0 ,12 chemical components of its essential oil. Zhongacaoyao, l4(3),
p-cymene 0 .3 8 0.36 0 .05 134-137(1993).
limonene+ 1,8-cineole 0.39 0 .3 1 0 .11 U. Ravid, E. Putievsly and I. Katzir, Determination of the
enantiomeric composition of *teryineol in essential oils. FIav.
terpinolene 0.05
1.03 Fragr.j., rO,281-284(1995).
linalool 1 .0 7 0.86
citronellal 0.o7 0.03 G. R. Mallavarapu,S.Ramesh,R. S.Chandrasekhara, B. R. Rajeswara
terpinen-4-ol U.UO 0.09 0.02 Rao, P. N. Kaul and A. K. Bhattacharya, Inaestigation of the
essential oil of cinnamnn Ieaf groun at B angaloreand H y derabad.
0-terpineol 0. 14 0 .1 0 0.10 Flav. Fragr.J., rO,239-242(1995).
piperitone 0.05 0.07
(E)-cinnamaldehyde 0. 41 0 .1 7 0.06 P. N. Kaul, A. K. Bhattacharyaand B. R. RajeswaraRao, Seasonal
eugenol 91. 08 93.94 83.03 Da4ation in the composition of the essential oil of cinnamon
( Cinnamomum zeylanicum Blume) leaoes.Indian Perfum., 4O(2),
B-elemene 0.28 0.34 0.23 36-38(1996).
(E)-cinnamylacetate 0. 12 0 .1 9 0.02
S.C. Nath, M. G. PathakandA. Barauah,Benzqlbenzoate,themajor
B-caryophyllene 0.66 0"48 0.46
component of the leaf and stem bark oil of Cinnamomum
n-humulene 0. 17 0 .1 2 0.10
zeqlanicumBlume. I. Essent.Oil. Res.,8, 327-328( 1996).
eugenylacetate 0.92 1 .0 7 1 0.02
5-cadinene 0.09 0 .0 6 0.91
caryophylleneoxide 0.36 0.26 0.02
benzylbenzoate 0.42 0.43 6.83
 Progress in Essential Oils
Reprinted
fromPerfumer
& Flavorist, 1gg7, Vol.22,No.6, p. 45
November/December

Neroli Oiland Orange Flower lsolates

Table L Comparativechemical composition (o/o)
Neroli oil and orange flower extracts are obtained from the of orange flower absolute, orange flower water
carefullyharvestedflowers ofbitter orange (Citrus aurantium absolute and neroli oil
L. ssp.amara). Both neroli oil, orange flower absolute and
orangeflower water absolutesare important perfumery raw Orange Orange
materials. flower flower Neroli
Compound absolute waterabsolute o i l
A survey of the Iiterature reveals that in 1g5g Triebs and
Bournot reported that the compounds known to occur in o-pinene I 0. 8
neroli oil were: B-pinene 0.4 1.1 15. 0
myrcene 0.1 t.o
hydrocarbons*.(35%) (+)-nerolidol(6%) limonene+ (Z)-B-ocimene 5 . 1 0.5 to. I
(-)-linalool(30%) methylanthranilate(0.6%)
(E)-B-ocimene u.o 0.2 6.0
(-) -|inalyl acetale (7ok) indole(<0.1%)
linalool 32.0 44.2 30.6
(+)-a-terpineol (2%) freeacidsand phenols(0.1.io)
geraniol+ nerol (4%) 2-phenethylalcohol 1.9
geranylacetate+ neryl s-terpineol 2.4 18.5 3. 0
acelale (47o) citronellol 0.5 0.2 0. 2
nerol 0.9 2.8 0. 5
-'comprised ol o-pinene, camphene, limoneneand heptacosane linalylacetate 16.8 9. 1
geraniol 1.5 6.4 2. 0
Three yearslater, Bigi (1962)reviewed the production of
neroii and orange flower absolute. In this ."rri"*, he noted indole 1.0 0.1 0. 1
that neroli oil was known to contain: methylanthranilate 3.0 A1
0. 3
eugenol 0.3 0.5
linalool(30%) methylanthranilate(0.6%) nerylacetate 0.8 0.5 1. 7
linalylacetate(7%) indole( 0. 1% )
nerol+ geraniol(4%) citronellylacetate 0.1
hydrocarbons*.(35%)
geranylacetate 0.6 u.3 ).n
o-terpineol(2%) othercompounds..-(11.2%)
nerolidol* t.o 1.7 4. 0
nerolidol(6%) acids,includingacetopalmitic
farnesol* 7.7 4. 0
acids(0.1%)
* correct
isomernot identified;t = trace (< 0.1%)
-- includingp-ocimene,limonene,camphene, o-pinene and heptacosane
--- includingdecanal,jasmone, farnesol, benzoic acid and esters and some
unidentified phenylacetates

In 1971,McHale proved that (E)-B-ocimenewas a com- In 19B2, Kaiser and Lamparsky examined the nitrogen-
ponent of neroli bigarde oil. The followingyear,Balboaet al. containing components of orange flower absolute and its
1972)usedTLC to tentativelyidentify a few componentsin headspace.Using a combination of analytical techniques
bitter orange flower oil of Eg,ptian origin. The components they identified the following constituents:
rentatively identifi ed were : methylanthranilate(6.5%)geranialdoxime
ethylanthranilate
(t) (6E){arnesal
oxime
limonene geranial N-methylmethylanthranilate methylheptenone isooxazoline
Iinalylacetate linalool indole(5.0%) nonanaldoxime
methylanthranilate o,-terpineol N{ormyl methylanthranilate decanaldoxime
neral nerol (t) undecanaldoxime
N-acetylmethylanthranilate nonylnitrile
\ine years later Buccellato (1981) compared the major
(0.03%) decylnitrile
:omponent compositionsof orange flower absolute,orange phenylacetonitrile
(1.5%) undecylnitrile
llos-er water absolute and neroli oil. The results of this study phenylacetaldoxime (2.0%) 1-methyl-2-ethylpyridine
1re seenin Table I. t* 1-nitro-2-phenylethane 2-acetylpyridine
This same year, Prager and Misklewicz (1981) used GC (0.4%) quinoline
methylheptenone oxime 2-methylquinoline
:nd GC/MS to examine the composition of a number of
geranylacetoneoxime 6-methylquinoline
samples of neroli oil, orange flower"firater absolute and neraldoxime 2-methylbutyrylnitrile--
:,rangeflower absolute.Their resultscan be found in Tables
II and III. -* found in headspaceonly
t = trace (< 0.1%)
 Table ll. Chemicalcomposition (%) of neroli oils Table lll. Comparativechemical composition (o/o)
of orange flower water absolute
Compound Percentagerange Average and orange flower absolute

cr- pin en e 0. 7- 1. 9 1. 1
Orange flower Orange
B -pin en e 11. 0- 23. 0 16.0 water absolute flowerabsolute
sabin en e 1. 0- 3. 3 1.7
myrcen e 1. 1- 2. 2 1.7 Percentage Percentage
Compound range Average range Average
lim o ne ne 9. 0- 17. 0 13.0
(Z)-B-ocimene 0.5-1.0 0.7 B-pinene 0-1.1 0.5 0-2.7 0 .9
(E)-B-ocimene 3.2-8.2 5.6 myrcene - 0-0.5 0.2
lina loo l 31. 0- 41. 0 36.0 limonene o-2.2 0.7 0-3.6 2 .0
(E)-B-ocimene - 0-2.2 1 .0
linalylacetate 3.4-7.6 5.0
terpinen-4-ol+ B-caryophyllene 0.3-1.6 0.8 frans-linalooloxide+ 1.0-3.7 2.5
c{,-terpineol 2.8-4.9 4.O cis-linalooloxide+ 0.6-2.3 t- o

nerylacetate 1.3-2,0 1.5 linalool 40.0-53.0 48.0 34.0-48.0 42-0

l i nal \/l anAtatp O - 2.4 1.0 1 4 . 0 - 2 1 .0 1 8 .0
n e r a n rrl a ccte te 2.5- 4.1 2- g
nerol 0.5-1.2 0.9 terpinen-4-ol
+
geraniol 1.2-2.9 2.2 B-caryophyllene 0.6-2.0 1.0 0-0.8 0 .4
nerolidol- 1.4-5.6 3.6 oterpineol 13.0-22.0 16.0 1.5-3.7 2 "1
nerylacetate 0-0.6 0.4 0-0.7 0.5
methylanthranilate 0-0.5 0.2
farnesol* 0.9-2.8 0.9 geranylacetate 0-1.1 0.7 0-1.3 1 .0
indole 0-3.2 1.3 nerol 1.7-2.7 2.4 0 - 1. 1 0 .6
geraniol 3.8-7.6 o. l 0-2.0 1.1
. correctisomernol identified 2-phenethylalcohol 0.9-3.9 2.1 0-2.1 0 .9
benzylcyanide 0.8-5.0 2.5 0-1.1 0 .7
nerolidol- 0-1.5 0.8 4.9-8.9 6.8
The authors presented quantitative data only for those methylanthranilate 2.0-11.4 5.8 1.0-4.3 2 .8
compounds for which the quantitative data is included farnesol* 0-1.9 0.9 3 . 6 - 1 5 .4 8 .7
aDove. indole 0-3.2 1.3 2.6-9.9 4 .5
Four yearslater, Srinivas(1986) compared the composi- * correctisomernot identified;+ furanoidform
tions of neroli oil produced in various countries such as
Algeria, Egrut, Italy, Spain and Tunisia. A surnmary of his
GC/MS analvsescan be found in Table IV. In 1988, Ma et al. compared the compositionof neroli oil
Also in igSO, it was reported by Kaiser that trace produced in Chinawith that of the headspaceof picked bitter
amounts of 2-isobutyl-4-methylpyridineand 2-isobutenyl- orange flowers. The authors used a combination of GC/MS
4-methylpyridine were characterized as constituents of and retention indices on trvo colurnnsof differing polarity as
orange flower absolute. their method of analysis.The resultsof this study are summa-
An oil produced from the flowers of the bitter orangetree rized in Table V
rvas analyzed bv a combination of'GC/MS and retention The flower oil of bitter orangesgrowr) in Spain was the
indices (Lin et al., 1986). The oil r.vasfound to possessthe subject of analysisby Boelens and Sindreu (1988). In tliis
following composition: study the authors identified the following components:
o-thujene(t) linalylacetate(18.39%) o,-thujene (0.1%) uterpineol(2.09.)
o-pinene(O.28%) geranial(0,04%) o - p i n e n e( 1 . 1 %) nerol(0.5%)
camphene(0.02'/.) frans_linaloolo*;6s++(0"09%) camphene(0.05%) geraniol(4.25'/")
B-pinene(0.53%) methylanthranilate(t) sabinene(2.8%) linalylacetate(2.8%)
myrcene(6.26%) acetate(t)
o,-terpinyl B-pinene ( 1 1 . B %) o-terpinylacetate(0.2%)
limo ne ne(9.1 3% ) o";6s++(0 07%)
cls_linalool 6-3-carene (0.1%) nerylacetate(0.9%)
B-ocimene. (3.91%) nerylacetate(1.09%) myrcene(1.7%) geranylacetate(1.7%)
frans_linalooloxide+(0.15%) geranylacetate(2.15%) o-phellandrene (0.05%) cls- and frans-linalool oxidet
linalool(50"46olo) nonanal(t) o-terpinene (0.5%) ( 0 . 1 %)
terpinen-4-ol (0.11%) B-caryophyllene (0.13%) l i m o n e n e( 1 6 . 6 %) cls- and trans-anhydrolinalool
cr-terpineol(4.75%) o-humulene(t) B-phellandrene (0.4%) oxide+(0.05%)
trans-pinocarveol (t) y-muurolene(t) (Z)-B-ocimene (0.5%) perillene(t)
nerol (t) (Z)-nerolidol(o.64%) (E)-B-ocimene (6.0%) neral (t)
neral(0.5%) farnesol-(t) y-terpinene (1.0%) geranial(t)
geraniol(t) (E)-nerglidol(1.09%) terpinolene (0.4%) B-elemene (0.1%)
p-cymene(t) B-caryophyllene (0.5%)
* correct isomer not identified cx-p-dimethylstyrene (t) bisabolene.(0.1%)
+ furanoid form
++pyranoidform linalool(37.5%) c r - h u m u l e n(e0 . 1 %)
t = trace (< 0.01%) terpinen-4-ol (0.75%) germacrene D (0.1%)
 Table lV. Comparisonbetweencompositions (%) Table V. Comparative chemical composition (o/o)of
of neroli oils of various geographicalorigins neroli oil and bitter orange flower headspace

Algerian Egyptian ltalian Spanish Tunisian Bitter orange

Compound oil oil oil oil oil Compound Nerolioil flower headspace
0-prnene 0.95 0. 86 1. 24 1. 18 1.35 (E)-2-hexenol 0.09
B-pinene 9. 31 7.42 8.22 9.97 14.08 toluene 0 .10
sabinene 7.24 5. 27 9, 12 7. 93 9.53 o(-thujene 1 .5 9
myrcene 2. 07 3. 76 9. 34 1. 87 1.97 campnene 0.08
cl{erpinene 0.59 0.74 p-mentha-1
(7),2-dienet 3.33
limonene 15. 35 18. 12 15. 05 15. 60 12.58 B-pinene o.ta 20.95
+
B-phellandrene myrcene 0.07 0.96
(Z)-B-ocimene 1.02 0.98 0.86 0.66 0.78 limonene 1.06 45.90
Tterpinene 7.92 8.34 7.34 2.75 6.98 (E)-p-ocimene 0.40 2 .0 2
p-cymene 0. 15 0. 17 0.56 0.05 ci+linalooloxide- 0.04
terpinolene 0.45 o.71 0.66 o .1 7 0.43 frans-linalool
oxide. 0.04
cis-linalooloxide+ 0.05 0.05 0.08 0 .0 8 0.11 3-cyclohexenylcarbinolt o.oa 0.08
frans-linalooloxide+0.05 0.02 0.05 0.24 0.02 linalool 73.72 6 .8 7
linalool 25.48 29.99 31.23 38.81 29.00 linalylacetate 16.53 1 6 .6 9
linalylacetate 5.29 9.45 4.90 2.48 3.84 nerol 0.19
terpinen-4-ol 0.17 1 .5 9 1 .9 0 0 .4 3 0.53 1H-indole 0.83
B-terpineol- 0.60 0.32 0.50 0.85 0.52 methylanthranilate o.25
c[terpineol 2. 26 2.59 2.96 3.09 3.35 nerylacetate 0.45
citronellol 4.08 2.21 2.81 3.59 3.08 geranylacetate o.21
nerol 0.79 0.64 0.81 0.48 0.77 isocaryophyllene 0.09 0.22
gera nio l 1. 99 2 .0 0 1 .7 ' t 1 .5 0 4.09 cr-humulene 0.06 0.11
nerolidol- 6.88 2.76 3.03 4.61 4.33 benzylalcohol 0.15
methylanthranilate 0.31 0.85 0.36 0.13 0.26 (Z)-nerolidol 1.18
farnesol* 0 .7 2 - 1 .0 1 2.17 farnesol* 2.46
farnacrrl 4na+a+6* 0.03 1,2-benzene
dicarboxylicacidt0.09
aromadendrene 0.30
'correct isomernot identilied;I furanoidform
hexadecanoicacid 0.36
* isomeric
form not given;t tentativeidentification
6-cadinene(t) selinene.(t)
(Z){arnesene.+ nerolidol.(2.6%)
(E){arnesene-(0.1%) (Z){arnesol.+ (E)-tarnesol" linalool(50.4%) neral
valencene(t) ( 1. 05% ) linalooloxides-(0.15%) geranial
nerol nonanal
- correct isomer not identified;+ furanoidform; t = trace (< 0.01%) geraniol o,-terpineol
nerylacetate nerolidol.
This sameyear,Yangand Lee (1988)determined that the geranylacetate farnesol*
bergaptencontent of Eglptian, French and Algerian orange limonene methylanthranilate
flower absolute was 2,650 ppm, 545 ppm and 680 ppm, * correct
isomer not identified
respectively.F urthermore, the authors proved that photo-
toxicity of orange flower absolute was directly related to Although the authors did not present much quantitative
the bergapten content. The authors also identified berga- data,theydid determine that, on storage,the linalool content
motin epoxide found in orange flower absolute, but they decreased,andthe linalool oxidecontentincreasedtoI3.37o.
found that it was non-phototoxic. The amount and enantiomeric distribution of o(-Dinene.
Kaiser (19B8) reported that, based on his extensive B-pinene and limonene in neroli oil was examined by
headspaceanalysisof fragrant flowers, he would categorize Mosandl et al. (1990).They found the following distribution:
bitter orange flower as a "white floral image" aroma. In this o-pinene(2.5%)a( : (1S)-(-)-(77%)
1R)-(+)-(23%)
group of aromas,all white flowers examinedwere found to (24.8%)a(1
B-pinene R)-(+)-g%): (1S)-(-)-(e6%)
contain: limonene(44.5'/.)agR)-(+)-(97%)
: (aS)-(-)-(3%)
indole phenylacetaldoxime a amount found in the oil

methylanthranilate 1-nitro-2\-p
henylethane
Also in 1990,Germanaet al. comparedthe compositionof
Itwas reported (Linget al., 1986, cited in Ding) that bitter oils produced from the petals, pistils and stamens of five
orange flower oil produced in Chongqing (Sichuan, China) clonesof the bitter orangeflower grown in Sicily (TableVI).
contained: The differences between the various flower-oart oils is
 Table Vl. Comparativechemical composition (%) Table Vll. Comparativechemical composition (%)
of oils produced from the petals,pistils and stamens of the flower and bud oils of bitter orange
of five clones of bitter orange flower
Compound Flower oil Bud oil
Compound Petaloil Pistil oil Stamen oil ct-pinene 0.25
0 .3 1 -0 .7 5 0-0.58 0-0.50 B-pinene 4.85 0.10
7 .0 0 -1 1 .9 4 0.50-9.53 0.27-0.89 sabinene 0.66 0.02
sabinene 0.27-0.56 0.08-0.71 0- 0. 13 myrcene 1.34 0.01
myrcene 0.56-1 .48 0. 33- 1. 65 0.06-1.61 limonene 7.15 0.49
limonene 8.89-25.28 8. 98- 18. 66 0.45-2.O0 cl-terpinene 5.64
ci-terpinene 1.28-7.59 7. 04- 10. 60 0. 13- 1. 1 5 B-caryophyllene | -zJ 0 . 11
0.37-0.84 1.36-2.1
3 0. 11- 0 . 4 7 linalool 53.19 95.21
B-caryophyllene
linalool 44.49-57.60 47.52-64.38 12.73-21 .34 benzaldehyde 0.22
benzaldehyde 0.42-0.60 0.39-0.50 c[-terpineol Y./O 0.04
0.09-0.25 2.95-5.05 2.88-3.77 nan/l rnatrta 0.48 0.46
nerylacetate 0. 61- 0. 89 0. 08- 1. 02 0.72-3.20 neral 3.70 0.93
neral 1. 85- 6. 67 1. 92- 2. 51 10.32-19.20 geranylacetate 1.08 0.65
geranylacetate 0.64-3.52 0.94-5.51 4.06-5.66 geranial 1.05 0.99
geranial 1.10-5.31 0. 52- 2. 18 5. 04- 1 0 . 3 6 nerol 0.98 0 . 10
nerol 0. 31- 0. 91 0. 10- 0. 47 0.44-1.02 geraniol 0.45 0.31
geraniol 1.39-3.65 0-0.29 12.28-14.27 methylanthranilate 0.08
methylanthranilate 0.10-0.38 0.96-2.04 1. 12 - 2 . 0 0 farnesol* 7.55 0,22
farnesol* 0.95-2.02 0. 48- 1. 63 29.45-34.06
- correctisomernot identified
t correctisomernot identified

interesting, particularly with respect to the hydrocarbon nerolidol-(2.587.) (0.10%)

methylanthranilate
cr-muurolol (0.02%) methylN-methylanthranilate
content of the petal and pistil oil compared to the stamen oil.
(Z,E){arnesol (0.04%) ( 0 . 1 0 %)
This latter oil is extremely rich in oxygenated constituents (E,E){arnesol (1.48%) cisjasmone (0.05%)
compared with the other two oils. 2-phenethanol(0.20%) methyljasmonate(0"01%)
A second paper by Germana et al. (1990) compared the i n d o l e( 0 . 1 6 %) geranylacetone(0.05%)
composition of whole Sicilian bitter orange flower oil with
* correcl isomer not identified:+ furanoidform
that of bud oil. These results are summarized in Table VII.
The following year, Boelens and Oporto (1991) reported In 1993, Toyoda et al. examinedthe headspacevolatiles
that neroli oil of Spanish origin was found to contain the of the flowers of various Citrus species grown in japan.
following constituents: Although the authors did not present useful quantitative
data, they did prove that the following constituents were
cr-thujene(0.05%) octanal(0.02%)
a-pinene(0.75%) nonanal(0.01%) present in neroli oil and C. aarantium ssp,amara absolute:
camphene(0.05%) geranial(0.10%) myrcene B-caryophyllene
sabinene(2.26'/.) linalool(8.93o/.) Iimonene oterpineol
B-pinene(0.52"/.) terpinen-4-ol(0.42","1 B-phellandrene nerol
myrcene(2.49%) o{erpineol (3.30%) geranrol
o-phellandrene(0.04'/.) nerol(0.82%) p-cymene 2-phenethylalcohol
6-3-carene (0.05%) geraniol(2.18%) linalooloxideisomers. phenylacetonitrile
o,-terpinene (0.18%) linalylacetate(6.37%) benzaldehyde nerolidol-
p-cymene(0.22'/") crterpinylacetate(0.06%) linalool methylanthranilate
limonene(12.88%) citronellylacetate(0.09%) l i ^ ^ t.,t
i l r ta tyt a^ ^u^Eta
+^ +^
tg indole
(Z)-p-ocimene(0.82'/") nerylacetate(1.36%)
(E)-B-ocimene (5.60%) geranylacetate(2.65'/.)
y-terpinene(0.33%) limonen-1O-yl acetate(0.02'/")
Also in 1993, Remy et al. compared the composition of
terpinolene (0.42%) B-elemeneJp.05%)
2,2,6{rimethyl-6- (0.54%) fresh Tunisian orangeflower lvater absoluteand an absolute
B-caryophyllene
vinyltetrahydropyran (Z)-B-faraesene (0.08%) produced from orangeflower water after it had been stored
(0.04'/") o,-humulene (0.18%) {br one month. The results of this analvsiscan be found in
cis-linalooloxide+(0.07%) germacrpneD (0.05%) Table VIII.
frans-linalooloxide+(0.02%) (E)-B-farnesene (0.13%)
This same yeal Surburg et al. (1993) characterized
perillene(0.02'/.) valencene(0.05%)
cls-limoneneoxide(0.03%) b-cadinene(0.03%) the following heterocyclic compounds in orange flower
frans-limonene oxide(0.03%) caryophyllene oxide(0.01%) absolute:
 linalool(15.59%) B-elemene (1.63%)
Table Vlll. Comparativechemical composition (%) 2-phenethylalcohol(0.01o/o) methylN-methylanthranilate
of fresh orange flower water absolute cls-p-menth-2-en- 1-ol ( s . 1 8 %)
and orange flower water absolute produced (0.0e%) e (0.72%)
B-caryophyllen
from water stored for one month lrans-p-menth-2-en- 1-ol lrans-o,-bergamotene (0.02%)
( 0 . 1 e %) rx-humulene (0.10%)
Compound Fresh oil "Storedoil" citronellal (0.06%) (Z)-B{arnesene (0.14%)
terpinen-4-ol (1.20%) germacreneD (0.05%)
methylheptenone 0.32 2 1 .0 0 a,-terpineol (1.79%) (E,E)-a{arnesene(0.07%)
linalooloxides. 5. 10 6.00 frans-piperitol (0.03%) 6-cadinene (0.03%)
linalool 47.80 27.00 nerol(0.69%) (Z)-nerolidol (t)
linalylacetate 0. 18 0.05 neral(0.41%) (E)-nerolidol (1.76%)
(r-terpineol 19. 80 25"00 linalylacetate(9.76%) spathulenol(0.02%)
nerylacetate geranial(0.65%) caryophyllene oxide(0.04%)
0.33 0.07
geranylacetate 0.70 0 .1 3 indole(0.06%) globulol(0.01%)
nerol 2.86 0.97 methylanthranilate (0.11%) o-cadinol(0.02%)
o-terpinylacetate(0.05%) (Z,E){arnesol (0.98%)
geraniol 8.25 0 .11 citronellylacetate(0.03%) (E,E)-farnesol (0.01%)
2-phenethylalcohol 2.54 0.57 nerylacetate(0.92%)
nerolidol- 0.70 0.23
methylanthranilate + furanoidform
2. 97 4.30
t = trace (< 0.0'1%)
farnesol" 1. 00 0.06
indole 1. 50 1 .4 0 This was the same data that was published two years
earlier (Mondello et al., 1994).Also in 1996, Tuchelkaet al.
- correctisomernot identified
reported the stereochemicalchiral GC analyiis of linalool,
Iinalyl acetate and u-terpineol using a heptakis-(2,3-di-O-
acetyl-6-O-tert. buq'ldimethyl-silyl)- B-cyclodextrin capiltary
3-phenylquinoline
(0.019"7
column and the same, simultaneous,analysisof o-pinene,
4-methyl-3-phenylpyridine
(0.001%)
4-ethyl-3-phenylpyridine
(0.0002%) B-pinene, Iimonene, terpinen-4-ol and (E)-nerolidol using
3-phenyl-4-propylpyridi
ne (0.0005o/o) a heptakis-(2,3-di-O-methyl-6-O-tert.butyl-dimethyl-silyl)-
2-methyl-5-phenylpyridine
(0.001%) B-cyclodextrincapillary column. They compared the enan-
2-ethyl-5-phenylpyridine
(0.001%) tiomeric distribution of the eight compoundsin a number of
ne (0.01o/o)
2-phenyl-2-propylpyridi
different lab-prepared oils and commercial samplesof oils
The following yeaa Ohloff (1994) reported that neroli oil {rom different origins.The enantiomericdistributionsof the
contained the following components: various compounds can be seen in TablesIX-XI. Examina-
(E)-B-ocimene tion of the datapresentedin thesetableswould indicate that
+ methylanthranilate (0.1%)
(Z)-B-oci
mene (6.5olo) indole( 0. 1% ) the French oif was adulterated and possibly one of the
B-pinene(11.0%) phenylacetronitrile
(0.1%) Tunisian oils aswell, becausethe enantiomeric distribution
limonen e(1 7% ) 1-nitro-2-phenylethane (0.15%) of linalyl acetate,terpinen-4-ol and (E)-nerolidol appearsto
linalylacetate(6%) isobutyl-3-methoxypyrazine be outside ofthe ernected levels.
(E)-nerolidol(3%) (1 ppm)
farnesol-(1%)
More recently,Monsandl and Juchelka(1997)presented
cr's-jasmone (0.02%)
the authenticity profile of neroli oil using both chiral GC
*
correct isomer not identified analysisand stable isotope ratio mass spectrometry both
A commercial sample of neroli oil that contained on-line coupled with capillaryGC. In addition to presenting
o-terpineol (4.6E")was determined by Ravid et al. (1995) to some of their data that was published in a previous article
existin the enantiomericratio of (4R)-(+)-u-terpine oI(477o) (Juchelkaet al., 1996), the authors presented an "isotopic
: (4S)-(-)-o-telpineol (53Vo). fingerprint" of some authentic neroli oils and compared
A year later, Mondello et al. (1996) used online HPLC- them with three commercialoils thatwere definitelvadulter-
HRCC and HPLC-GC/MS to examine the comoosition of ated. The value of this paper is that, although the examina-
Italian neroli oil. They found that the oil contained: tion of enantiomeric distribution of optically active oil
componentscan provide useful information on oil adultera-
tricyclene(0.01%) 6-3-carene(0.52o/o)
tion, the genuinenessof an oil can be accuratelydetermined
o,-thujene(0.25%) or-terpinene(0.51%)
a-pinene(1.31%) p-cymene(1.04%) only by a combination of enantiomeric distribution of oil
camphene(0.04%) limonene(24.W") componentsand their stableisotope ratios.
benzaldehyde (0.01%) (Z)-B-ocimeqe (0.34%) Also in 1997,Boelensand Boelenscompared the chemi-
sabinene+ B-pinene (E)-B-ocimene (3.60%) cal composition of bitter orange flower til produced bv
(2O.22%) y-terpinene(3,.21V4
steamdistillation from flowers harvestedin Spainand Tuni-
6-methyl-5-hepten-2-one frans-sabinene hydrate(0.09%)
(0.11%) o,,;6sf(0.02%)
cr.s-linalool sia. The authors further compaled these analytical results
myrcene(2.33%) terpinolene(0.53%) with those obtained from the analysisof a CO, extr-actof
o-phellandrene (0.09%) cissabinenehydrate(0.03'/.) bitter orange flowers of Moroccan origin. Their results are
 Table lX. Enantiomericdistribution (%) of linalyl acetate,linalool and u-terpineolin neroli oil

Linalyl acetate Linalool o,-Terpineol

Numberof
Nerolioil samples samples R-(-) s-(+) R-(-) S-(+) R-(+) s-(-)
freshblossomoils 4 95.4-97.5 2.5-4.6 70.8-81.5 18.5-29.2 70.3-71.O 29.0-29.7
driedblossomoils 6 95.8-96.9 3.1-4.2 73-0-77.9 22.1-27.O 69.1-72.3 27.7-30.9
authenticMoroccanoils 3 96.0-96.2 3.8-4.0 71.0-71.4 28.6-29.0 69.4-70.1 29.9-30.6
commercialMoroccanoils 2 94.0-97.0 3.0-6.0 76.8-78.7 21.3-23.2 68.6-69.3 30.7-31.4
commercial
Tunisianoils 2 94.4-97.9 2.1-5.6 77.1-78.2 21.8-22.9 68.7-69.5 30. 5- 31. 3
commercial
Tunisianoils-- 1 62.8 37.2 72.6 27.4 60.2 39.8
commercialFrenchoil-. 1 BB.6 11.4 oJ. I 36.9 71.9 28.1
-- oil probablyadulterated

Table X. Enantiomericdistribution (%) of some monoterpenehydrocarbonsin neroli oil

o,-Pinene B-Pinene Limonene

Numberof
Nerolioil samples samples R-(+) s-(-) R-(+) s-(-) R-(+) s-(-)
freshblossomoils 4 8. 2- 12. 3 87.7-91.8 <0.1-0.1 99.9->99.9 97.0-98.1 1. 9- 3. 0
driedblossomoils 6 2. 2- 10. 4 89.6-97.8 < 0.1-0.8 99.2->99.9 93.1-95.7 4.3-6.9
autheniicMoroccanoils 3 11. 8- 13. 6 86.4-88.2 0.3-0.5 99.5-99.7 96.9-97.2 2. 8- 3. 1
commercialMoroccanoils 2 ' 13. 1- 13. 3 86.7-86.9 1.0 99.0 96.0-96.7 3.3-4.0
commercial
Tunisianoils 2 10. 5- 12. 3 87.7-89.5 0.1-0.3 99.7-99.9 95.8-98.3 1. 7- 4. 2
commercial
Tunisianoil 1 11. 9 88.1 2.9 97.1 97.1 2. 9
commercialFrenchoil 1 13. 1 86.9 4.0 96.0 96.7 J.J

Table Xl. Enantiomericdistribution (o/o)

ol terpinen-4-oland nerolidol

Terpinen-4-ol (E)-Nerolidol
Numberof
Neroli oil samples samples R-(-) s-(+) R-(-) S'(+)
fresh blossomoils 4 51. 0- 6 3 . 2 36.8-49.0 0.4-0.8 99.2-99.6
driedblossomoils o 56.4-64.7 35.3-43.6 0.9-1.8 98.2-99.1
authenticMoroccanoils J 62.4-64.0 36.0-37.6 LZ- 1.+ 98.6-98.8
commercialMoroccanoils 56.5-59.4 40.6-43.5 1.0-1.3 98.7-99.0
commercial
Tunisianoils 54.6-57.7 42.3-45.4 1.0 >9 9 " 0
commercial
Tunisianoil 1 64.9 35.1 1.6 98.4
commercialFrenchoil.. 1 41.2 58.8 33.4 66.6

-. oil probablyadulterated

summarizedin Table XII. The authors pointed out that the D. McHale, Thebasecatalyzedrearrangemento;fcis- andtrans-ft
major difference between the CO, extract and the oils was ocimene to trans- L-trans- 6-alloocimene.Tetrahedron, 27, 4843-
4844(r97r).
that linalyl acetate, a major component of the extract, was
S. I. Balboa,M. S. Hifnawy and M. S. Karawya,StudlJof theflouer
drasticallyreduced in the oils becauseof hydrolysisduring
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CI-pinene .13
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Mookherjeeand B. ]. Willis, pp 551-565,ElsevierSci.Publ. B.\2.,
B-pinene 1 0 .5 2 -1 3 .0 0 tz+.3b 8.79 Amsterdam (1988).
myrcene 1.40-3.09 2.08 1. 1 1
H-j. Yang and N -ALee,A study of the phototoxicity of orangefloa^er
s-lerpinene 0.18-0.48 0 .1 0 0.04
p-cymene absolute. In: Flaxors and,fragrances : A.*^odd p erspectiae.E dits.,
0 .0 1 -0 .0 5 0 .1 2 0.04
B. M. Lawrence, B. D. Mookherjee and B. M. Wilhs, pp 1039-
lrmonene 12.88-17.89 1 2 .2 0 11.5 0 1044, trlsevier Sci. Publ. 8.V., Amsterdam (1988).
(Z)-B-ocimene 0 .1 0 -0 .4 3 0.73 0.40 R. Kaiser, From headspacetroppingto reconstitutions of natural
(E)-B-ocimene 5.60-7.00 6.24 4.54 scents. Proceedinss of IFEAT International Conference on
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terpinolene 0.42-0.60 0.42 0. 1 6 1988,IFtrAT/Ministry of Light Industry, Berjing (1988).
hexyl acetate 0 .0 1 -0 .0 5 0.05 0.04 Z-K. Ling, Y-F. Hua and Y-H. Gu, The chemical constituents of the
cls-linalooloxide+ 0 .0 1 -0 .0 7 0 .1 6 o.22 essential oilfromthe flowers, leauesand p eelsof Citrus aurayttium.
lrans-linalooloxide+ 0 .1 0 -0 .2 0 0.06 0. 16 Acta Bot. Sinica,28, 635-640(1986).Cited In:D.Ding,Recent
linalool 31.37-47.05 37.87 34.60 pro gressof essentialoilsandflaaour analy sisinChlna. Proieedings
2-phenylethanol 0.06-0.25 0.64 ofthe IFEAT International Conference on essentialoils. flavours.
terpinen-4-ol 0 .3 1 -1
.3 2 o. 1 4 fragrancesand cosmetics,Beijing, Oct. 1988,IFEAT/Ministryof
0-terpineol 1.07-3.45 1. 1 3 Light Industry, Beijing (1988).
A. Mosandl, U. Hener, P. Kreis and H. G. Schmorr, Enantiome,ric
nerol 0.32-O.82 0.88 0.23
distribution of a-pinene, ftpinene andlimonene in essential oils
neral 0 .0 1 -0 .0 3 0.03
and.extracts. Part I. Ilutaceae and Craminae. Flav. Fragr. f., 5,
geraniol 0.80-2.28 2.00 0.40
193-199i1990).
linalylacetate 0 .5 8 -1 0 .0 0 3.30 23.60
M. A. Germana, F. De Pascuale,E. Bazan and E. P.afazzolo,
2-phenethylacetate 0.03 0. 1 8 Essential oils from dffirent pafts of the flowers of dffirent
geranial 0 .0 5 -0 .1 0 0.06 clonesof Citrus aurantiumL., EssenzeDeriv. Agrrrm.,60,287-
dterpinyl acetate 0 .0 1 -0 .3 0 0 .1 4 0. 14 296 i I 9907.
h ^ ^ ,1
rrEry r ^^^+ ^+
auEr dLE^ 0 .2 9 -1 .5 5 t.cJ 0.79
M. A. Germana, F. De Pascuale,E. Bazan and tr. Palazz.olo,
geranylacetate 0.70-2.95 2.94 1. 1 7 Essential oils of the floroers, leaoes,and burls of fiae speciestf
cls-jasmone 0 .0 1 -0 .0 5 0.02 u. t c Citrus., EssenzeDeriv. Agrum., 60, 297-312 (1990).
cls-methyljasmonate 0 .0 1 0 .0 1 0.03 M. H. Boelens and A. Oporto, Natural isolatesfrom Seaille bitter
phenylacetonitrile u. o/
orangetree.Perfum.Flavor.,t6(6), 1-7 (1991).
indole 0 .10 -0 .1
6 0 .1 6 0.45 T. Toyoda, I. Nohara and T. Sato, Headspace analysis of uolatile
methylanthranilate 0.10-0.22 0.09 0.98 compounds emitted from oarious citrus blo,s,soms.In:Bioactiue
B-caryophyllene 0.54-0.70 0.73 0.o7 uolatile compounds-from plants. Edits., R. Teranishi, R. G.
(E)-B{arnesene 0 .0 5 -0 .1 0 0 .1 7 Butteryand H. Sugiswara,ACS Sympos.SeriesNo. 525,pp205-
a-h umu len e 0 .0 6 -0 .1 5 0 .10 219, Amer. Chem. Soc.,Washington,DC (1993).
(E,E)-o{arnesene 0 .0 5 -0 .1 0 0 .1 1 M. Remy,J-C.Bayle,M. DerbesyandR.IJzro,TheTuttisian orange
7-eremene 0 .0 1 -0 .0 2 0"12 flouer water absohtte LMR. Rivista Ital. EPPOS, (Numero
6-cadinene 0 .0 1 -0 .0 3 0.03 speciale),593-602(1993).
(E)-nerolidol 2.15-3.37 3.36 H. Surburg, M. Guentert and H. Harder ,Volatile com,pounds from
(E,Z)-farnesol 0 .7 2 -1 .5 9 1 .5 7 flowers, Analytical and olfactorg aspects. In: Bioactiue uolatile
comltounrlsfrom pkrnt s . E dtts.R. Teranishi, R. G. Buttery and H.
= furanoidform
Sugisawa,pp168-186,ACSSl.mposiumSeries525,Amer.Chem.
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chemical perspectiaes. Translated by W. Pickenhagen and B. M.
90, Proceedingofthe VII International EssentialOil Congress,
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Cannes,pp 287-294,Fedarom, Grasse(l€82).
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S. R. Srinivas, Atla,sof essenti al oils. Publirbed by author, B ron-r,NY
high perfonnance liquid chromatography coupled uith high
r98 6).
resolution gas chromatography and massspectrometry @PLC -
Fi. Kaiser, Ne'**natural products of structlval and olfuctory interest HRGC-MS) for the analAsis of complex rnirtures containing
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Crur,ter. Berlin (1986).
U. Ravid, E. Putievsky and I. Katzir, Determination ttf the
enantiomeric compositionof a-te:ineol in essentialoils. Flav.
Fragr.J., r0, 28r-284 (1995).
On-line HPLC-
L. Mondello, G. Dugo, P. Dugo and K. D. !tsa:r.le,
HRGC inthe analytical chemistry of cihus essentialoils .Perfum.
Flavor.,2r(4), 25-49 (1996).
A. MosandI,Chiral compoundsof
'essential A. Steil,K. Witt and
D. Juchelka,
oils.XX . Chirality eaaluatinn and authenticitg profiles
of neroli andpetitgrain oils.l.Essent. Oil Res.,8, 487-497( 1996).
A. Mosandl and D. Juchelka, Adnoncesin the authenticity of citnts
oils.J. Essent.Oil Res.,9, 5-12 (1997).
M. H. Boelensand H. Boelens, Dffirences in chemicaland,sensory
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hy droclistillation andfrom supercritical C O, extraction. Perfum.
Flavor.,22(3), 31-35 (1997).
Menthacitrata Oal
ln 1972, Virmani et al. analyzed an oil of M. citrata
produced in Lucknow (India) using gas chromatography.
They found that the oil contained:
o-pinene(1.7%) B-phellandrene (3.3%)
B-pinene(2.0%) linalool(48.0olo)
limonene(1.3%) linalylacetate(32.0'/.)
Two years later, Kapil et al. (1974) determined that, in
addition to linalool and linalyl acetate, the water-soluble
fraction produced during oil distillation contained furfural,
acetone,formic acid, aceticacid, methanol and a number of
unidentified alcohols,ketonesand acids.Unfortunately the
authors did not provide any quantitative data.
Also in 1974, Paris et al. determined that a sample of
bergamot mint (M. citrata) oil that was produced in F rance
contained the following major components:

Taxonomists disagree about whether to treat this Mentha 1 , 8 - c i n e o l(e1 0 - 1 8 %) linalylacetate(6%)

linalool(55-61%) cr{erpineol(11%)
speciesas Mentha x citrata Ehrh. or a variety of M . aquatica
or a nothomorph of M. piperita. A survey of the literature In addition, the authors identified small undetermined
revealsthat it has been reported for some time that an oil amounts of componentssuch as:
known as lemon mint, lavender mint or bergamot mint cr,-prnene geraniol
containslinalool and linalyl acetate(Guenther 1949), B-pinene g-eudesmol
In 1963, Fujita reported that an oil produced from M. carvone B-eudesmol
citrata grown in Japan contained the following components: nerol T-euoesmol

(I-prnene linalool(30%) Four yearslater, Lawrence (197E)used a combination o{

B-pinene linalylacetate(40%) column chromatography, preparative and analyical GC and
limonene(0.1-0.3%) carvone infrared spectroscopyto analyzethe oils from three different
'1,B-cineole
strains of M. citrata. The compounds identified in the oils
As can be seen,incomplete quantitative data was reported. were:
The following year, Handa et al. (1964) used retention d,-pinene (0-0.1%) linalylacetate(42.0-78.4%)
time data to determine that an oil produced from M. citrata B-pinene(0-0.3%) o,-gurjunene (0-<0.1%)
grown in the United Statespossessedthe following compo- sabinene(0-0.2'/.) B-elemene (0-0.3%)
myrcene(0.5-1.3%) lavandulylacetate(0-1.4o/")
sition:
limonene(<0.1-0.4%) B-caryophyl lene (<0.1-2.1%)
o-pinene(0.6%) menthofuran (0.1%) 1,8-cineole (0.9-4.1 %) (E)-B{arnesene (0-0.5%)
B-pinene(0.9%) linalylacetate(45.0%) (Z)-B-oci mene(0.2-0.5%) cr{erpineol(0.6-7.3"/")
limonene(1.1ol.) pulegone( 8. 1% ) (E)-B-ocimene + T-terpinene nerylacetate(0.7-1.1'/")
1,8-cineole(0.2%) piperitone(4.2%) ( <0 . 1 - 0 . 6 %) germacrene D (0.2-0.7%)
linalool(32.4%) piperitoneoxide-(3.0%) p-cymene(0-0.1%) bicyclogermacrene + carvone
terpinolene (0-0.1%) ( 0 . 1 - 0 . 3 %)
* correct isomer not identified
3-octylacetate(<0.1-1.8%) geranylacetate(0.2-0.5%)
3-octanol(0.2-1.5%) 6-cadinene (<0.1-0.1%)
That same year, Nigam and Levi (1964) confirmed the
menthone(0-0.4%) citronellol (<0.1-0.8%)
presenceof menthofuran (0.05E")tnM. citrata oil.Two years menthofuran (0-<0.1%) geraniol(<0.1-1 .0%)
later, Sharmaet al. (1966) reported the same results as had isomenthone (0-0.2%) elemot(0-1.3%)
Handa et al. (1964). Also in 1966, Montes and Mizrahi isopinocamphone (0-0.2%) viridif lorol(<0.1-3.0%)
repofted that the major constituentsof an oil produced from l i n a l o o(l1 0 . 3 - 3 8 . 1 %)
NL citrata grown in Argentina were: In 1980, Singh et al. identified a new C, terpenoid
limonene linalool constituent in Indian M. citrato oil. Usine a combination of
1,8-cineole linalylacetate IR, 1H-NMR and MS, they elucidatedthe structureof this
Three years later, Shimizu et al. (1969) determined that hydrocarbon to be 1-vinyl-p-menth-4(8)-ene.
the oil of a strain of M. citrata grown iXf apan contained the Five yearslater, Grossoand Molna (1985) reported that
following major components: a sample of Argentinear M. citrata oil (which they noted as
being M. aquatica) contained:
cr-pinene(12.3'/") tinatootlzo.sz)
B-pinene(4.1%) linalylq.getate(22.9%) B-pinene(0.1%) B-caryophyllene(2.3%)
limonene(20.0'/") linaloolbxide. (7.0%) o-phellandrene (0.8%) menthol(trace)
limonene(0.2%) pulegone(trace)
.
correct isomer not identi{ied linalool(13.4%) carvone(4.5%)
llnalylacetate(66.2"/4
 In 1988,Shimizu determined that M. citrata oil produced
in Japancontained the following constituents: Table Xlll. Comparativechemicalcomposition (%)
of Argentinean M. citrata oils produced from plants
0,-pinene (0.55%) linalool(25.65%) harvested at two separate times
(1 .09 % )
B -p ine ne linalylacetate(53.24%)
myrcene(t) B-caryophyllene (1.31%)
limonene(t) menihol(0.38%) Oilfrom Oil from
1,8-cineole (9.39%) c-terpineol(1.75o/o) full-flowering post-flowering
menthone(t)
Compound plants plants
nerylacetate(0.39%)
trans-linalooloxidejuranoid geranylacetate(0.35%) 0-prnene 0.10 0.20
(0.26%) elemol(0.58%) B-pinene 0.70 0.80
myrcene 0.50 0.70
1,8-cineole 0.72 0 . 57
u;;;;-".", Shimizu proved that M. citrataoit contained
ltmonene 2.98 z-50
r3R) - t - ) - linalool. linalool 23.80 35.40
Using multidimensional gas chromatography,c,-pinene, cr.-terpineol 0.09 0.1 0
F-pinene and limonene were separatedinto their enantio- nerol 0.10 U. IJ

meric forms by "heart cutting" from a DB-1701 column onto
a heptahs (3-O-acetyl-2,6-di-O-pentyl)-B-cyclodextrin chiral
column (Mosandlet al., 1991).The enantiomericdistribu-
tion of thesemonoterpenehydrocarbonsinM. citrataoilwas
as follows:
o-pinene
S-(-)-(21%) : R-(+)-(79%)
S-(-)-(92%)
B-pinene : R-(+)-(s%)
limonene
S-(-)-(8%): R-(+)-(92%)
The enantiomeric distribution of citronellol (2.g%) iso-
lated from a sample of M. citrata oil produced in Israel was
fbund (Ravid et al., 1992)to be (R)-(+)-citronellol(SSVo):
( S)-(-)-citron ellol (477o).Using a y-cyclodextrinchiral Lipodex
column, Ravid et al. (1994) determined that the linalyl
acetate found in M. citrata oil was enantiomericallv oure
t R r-r- t - linal)I ac et a te .
Oils produced from four strains of M. citrata grown in
Israel were found to contain minor quantitiesof u-terpineol
(2.7-4.2Ea).Ravid et al. (1995) determined that its enantio-
meric distribution was (4R)- ( + )-o-terpineol (69-317o) : (4S) -
(-)-o-terplneol ( 19-3t % ).
More recently,Malizia et a1.(1996)used a combinationof
GC and GC/MS to analyzeoils produced from Argentinean
grown M. citrata at two different growth stages.Their results
are summarized in Table XIII. As can be seen,the linalool
and linalyl acetatecontents varied depending on the matu-
rity of the plants used to produce the oil.
E. Guenther, Theessentialoils.Vol III, pp 685-686,D. VanNostrand
Co.,Inc.,Princeton,NJ (1949).
Y. Fujita,OnMenthacitrataEhrh. j. Jap.Bot.,38,171-f74 (1963).
K. L. Handa,D. M. Smith,I.C. NigamandL. Lei,Essentialoilsand
their constihtents
XXIil. Chentotaxonomy of the genusMentha.
j. Pharm.Sci.,53,1407-1409 (1964).
I. C. Nigam and L. Levi, Essentialoilsandtheir constituents.XX.
Detectionand estimationof menthofuranin Mentha ar-aensis
anrl other mint ,species bq coupiedgasJiqtLid-thin-layer
chromntography. J.Pharm.Sci.,53, 100f810i3(f964).
M. L. Sharma,M. C. Nigarr,K. L. HandaandP. R. F:ao,Chemical
and gas_chromatogmphic inDestigatiolrof linalool and linalyl
acetatebearingplants in India.IndianOil SoapJ.,31, 303-307
(1e66).
A. L. Montes and L Mizrahi, E,ssentialoils
of Menthacitrata,Mentha
rotundfolia ancl Mentha canadensis.An. Soc. Cient. Argentina,
181(3/4),49-60(1966).
carvone 0.05 0 . 12
geraniol 0.12 0 . 18
linalylacetate 60.90 48.65
nerylacetate o.70 0 . 50
geranylacelate 0.70 0 . 45
caryophylleneoxide 0.35 0.25
S. Shimizu, D. Karasawaand N. Ikeda, Studies on the essential oils
tf Mentha aquatica L. I-ilL. J. Fac. Agric. Shinisu Univ., 6,
67-82(1969).
o P.^Virmani, M. C. Nigam and S. C. Datta, Ga-schromatographrl
of the essentialoil of Mentha citrata raised in Lucknou.lndiai
Perlum., r6(II), 1-2 (1972).
B. Kapil, B. C. Gulati and G. K. Singh, Chemical studie,sof
essentialoil of Mentha citrata. I. Physiochemicalstudq of dffirent
oil samples and uater soluble constituents. Indian Perfun'r.,
r 8 ( 1 ) , 4 1 - 4 6( 1 9 7 4 ) .
M. Paris,C. A. L. Bercht,J. Unger and G. Clair,InterAtdelaMenthe-
bergamote en aromatique. Rivista Ital. EppOS, f l, 655-658
(re74).
B. M. Lawrence, A study of the monoterpene interrelationships in
the genus Menthawith specialreferenceto the Ltrigin ofpulegone
and PhD thesis, Rijksuniversiteit, Groningen,
-menthofuran.
Netherlands (1978).
R. B. Singh, A. Goswami, M. C. Nigam and R. S. Thakur,
1-V iny lmenth- 4 (B) -ene, a t ew enoi tl h y d roca rb o n fro m M entha
citrata. Phytochemistry,f9, 2466 (19S0).
M. B. de Grossoand P. Mo1ma,Comlt osicion Quimi ca delas esencias
de Mentha del Uruguay. An. Real. Acadl Farm., 51, 333-338
(1e85).
S. Shimizu, Studieson the mints containing dextro- orleao-rotatory
linalool as a dominant constituent in the essentialoils. Bull. Iidi
Women's Junior College (japan), 9, 24-33 (1988).A. Mosandl,
K. Fischer, U. Hener, P. Kreis, K. Rettinger, V. Schubert and
H. G. Schmar,Stereoisomt ricflau,rr c'ompoi nds 48.Chirospecific
analy sisof n aturalJlaa orsand esset'rtialo ilsusingm:ultidimensionul
gas chromatographA.J.Agric. Food Chem.. 39, 1131-1134
(199r
)
Ravid, E. Putievsly, I. Katzir, R. Ikan and V. Weinstein,
Determination of the enantiomeric comltosition of citronellol in
es.sentialoils by chiral GC anaQlsison a modified ycyclodextrin
phase.Flav. Fragr. J., 7,235-238 (1992).
Ravid, E. Putievslg, and I. Katzir, Chiral CC analysis of
enantiomerically pure (R)-(-)-linalql acetatein someLantiaceae.
Mqtle and Petitgrain essentialoi1s.Flav. Fragr. J.. 9,275-2i6
( 1994)
U. Ravid, E. Putievslg' and I. Katzir, Determination of the More recently, Khanna et al. (1988) identified 17 con-
enantiomeric composition of a-terpineol in essentialolls., Flav. stituents in an oil that was produced in 4.5Voyield from the
Fragr.J., 10,281-284(1995).
fruit rind of C. glaucescens.The compounds that were
R. A. Malizia, j. S. Molli, D. A. Cardell and j. A. Retamar,Essential identified only by retention time on a packed GC column
oil of Mentha citrata groon in Argentina. Yariation in tht
comlto,sitionand rlield at full- and post-flouering. J. Essent. Oil
were:
Res..8. 347-349(1996). cx,-pinene (2.25"/") terpinen-4-ol(4.05'/.)
B-pinene(2.99%) linalylacetate--(1.25%)
Su gandha K ok il a Oi l limonene(2.74%) crterpineol(4.05%)
1,8-cineole (5.92'/") methylcinnamaIe (6.70%)
A very limited amount of Sugandha(sometimesSugandh) ^f-terpinene (26.74o/o) thymol(3.64%)
kokila oil is produced in Nepal and sold in Europe and India. p-cymene(2.02%) salrole(17.42%)
It is produced from the fruit of Ci,nnamomum glaucescens elemicin.*(6.90%) eugenol(5.82%)
(Nees) Drury (syn.C. cecidodaphneMeissn.) that is found in linalool(8.46%) nerol--(8.94%)
B-caryophyllen e (2.79%)
the Dang and Rolpa districts of the midwestern develop-
ment region of Nepal. .- misidentifications
based on lhe elutionorder on a Dolar-packedcolumn
In 1967, Singh et al. reported that an oil produced from
AIsoin 1988,Adhikary and Tuladharexamineda Nepalese
the dried pericarps of the fruit contained:
fruit oil of C. glaucesc@nsusing TLC and GCIMS. They
cr-pinene + B-pinene (22.5%) found that the oil contained:
( 10. 1 % )
1, 8- c ineole
methylcinnamate (16"0%)

Table XfV. Comparative chemical composition (%) of the fruit and pericarp oils of Cinnamomum glaucescens

Gompound Fruitoil Pericarpoil Compound Fruit oil Pericarpoil

o-prnene 1 .2 2.7 epi-B-santalene 0.1

crthujene 0 .3 u.\t p-santalene 0.8
campnene 0 .1 0.1 cr-humulene t-J

B-pinene 1 .9 4.2 6-terpineol 0.4 1. 0

sabinene 0 .8 9.5 neral 0.3 0. 1
myrcene 0 .4 0 .6 o{erpineol 6.6 9. 5
a-phellandrene <0.1 2-undecanol < 0.1
o,-terprnene 0 .4 <0.1 B-selinene 1.0
limonene 0 .5 0 .5 nan/l rnotata 0.3
Q hi^^k^t^-^
B-phellandrene 1 .4 0 .4 p-urDduvrEr lE 1.1
1,8-cineole 1 3 .1 56-,2 0-selinene 0.6
(Z)-B-ocimene < 0 .1 geranial 0.5
y-terpinene 0 .6 0 .1 6-cadinene 2.9
(E)-B-ocimene 0 .2 methyllaurate o.2 0. 2
sryrene 0 .1 calamenene* 0.3
p-cymene 3 .6 r .a geraniol 0.2
terpinolene 0 .3 <0"1 p-cymen-8-ol 0.1
2-nonanone 1 .9 d-caracorene 0.1
s-cubebene 0 .7 <0.1 (Z)-methylcinnamate 0. 2
s-copaene 4 .7 0.3 caryophylleneoxide 0.7 0. 3
2-nonanol 0.2 methyleugenol 0.6
camphor 1 .5 (E)-methyl
cinnamate 13.7
linalool 2 .8 ).n spathulenol 0.5 0. 1
1-ol
trans-p-menth-2-en- 0 .1 o.2 (E)-methyl
isoeugenol 0.4
s-santalene 2-1 0.3 p-menth-5-ene-1,2-diol u.z
o-bergamotene. 0.7 carvacrol 0.4
B-elemene 0.3 elemicin 0.2
2-undecanone 3.6 .4 capricacid 1.3 0. 1

B-caryophyllene 7.4, 0.4 myristicin 2.5

terpinen-4-ol 4. 0 2.6 lauricacid 2.7 0. 2
aromadendrene 0.4\rr
1-ol
cls-p-menth-2-en- 0. 1 o.2

- correctisomernot identified

168
 tx-prnene d,-copaene globulol(0-0.36%) y-muurolol
(0-<0.01%)
B-pinene campnor T-cadinol(0-<0.01%) or-cadinol
(0-0.30%)
sabinene(9.5%) linalool
o.-phellandrene B-caryophyllene " correct isomer not identified
lrmonene oterpineol(7.5%)
1,8-cineole
(36.8%) Tliese sameauthorsalsoexaminedthe compositionof the
methylcinnamate(16.0%)
oils of P raccnlosavar.gri,sea(Kiaerskor-)posb., g rocemosa
The authors presented quantitative data only {br the major var. lti,spanict/erzsl,s
(Urban) Landrunr and.p. raceni,osdvar.
constituents. ozuo.(Urban et E. Ekm:rn) Landrum. Thev shou,edthat the
\4or:erecentl)',Adhik:rrvetal. (1992)compareclthe chemi_
. ylajor comprinent of the oil of r-ar. grlsea nas geraniol
czilcornpositionof tlre fruit and pericarp oils of NepaleseC. (85.525a),(E )-methyl isoeugenol(85.08-86.32Zo) oimethyl
glottcescens. Using a combination of chromatog.apilc tech- eugenol (92.60Eo).The oil ol var.hisrtaniolen,sis n.asrich in
niques,nrchrdingsilicagel column chromatograph! CC and
one of the fbllorvingcombinations:1,8-cineole(37.g62o)and
GC/N,IS,andr3C-NMR of the whole oil, a detailedanalysis terpinen-4-oI(28.98Eo);1,S-cineole'17.87E")and methvi
r.-asperformed. A summaryof the resultsof this study can be
errgenol (63.8870);1,S -ci neol e(27.50E a),terpi nen_4_ol
seenin Table XI\,1
and methl,l chavicol (22.6IVo):or y-terpincne
]9?!/")
(I6.67E")and thvrnol (41.02Vo).Incontr:rst,the oil o{ var.
-\. Snrglr,S.N. Srivastavtr anclV. N. Sharma, Clrcmicolexartilnatiorr o71te\\raslbund to contain lirnonene (3.62-30.07Vo),I.g_
oJ.tlrcesserttialoilfrotn theftuit s of Cinnamonrumcer:icLt rlal:hna
Perfum.,f l(2),21 (1967). cineole (47.24-55.93%),terpiner-r-4-ol(4.00-18.670/o)and.
-llclssn.Indian
R K,,Khanlrr.J.^K,Jorrhari,O. S. ShannaandA. Singh,Essential o,-terpineol (6.68-15.IzEo).Since the eusenol content for
,,ilJr,tnttlu^.fntit rind of Cinnamornum cecidod.aphne L[eissrt. these other P. racemosar-arietieshas been found to be less
IndianPerfum.,32, 294-300 (1988). than2Vo,it would be unusualthat mixed varietiesu,ouiclever
S. R. Adhikarvtrnd B. S. Tuladhar,Es,sential oil front tltefnLits of be usedasrar.vm:rterialsto produce the bav oil of commerce.
I yt y yy yirury1glatLcesc ens(Nees) Drun1.J.Neial pharrn.Assoc_ In 1995,Bello et al. useJ GC/MS to cleienninethe maior
1 5 .1- 7( r eB B ) . components o{'the oil of p. racentosrz(of unkncxunvar.iei,rl
S R Adhikary,B. S. Tuladhar,A. Sheak,T. A. van Beek,M. A. origin) produced from leaves harvested in rvestern Cuba.
Postlrumus andG.P.Le\veld, Int c:;tigation ofNcpalese esserttial They found that the rnajor componentsin this oil u,ere:
oil* l. the oil of Cinnon,,ntuttt g!aur'e.scctt.riSugantlhakokita).
J. Essent. Oil Res.,4, 151-159 (1992). 1,8-crneole
(20.42/") (10.13%)
chavicol
terpi nen-4-ol (2O.72" ) eugenol (10.71..)
Ba y Oi l cr-terpineol
+ methylchavicol
(10.78o/.)
h 1991,Tucker et al. anaivzedthe chemical compositionof
:.\ o colr'rlrlercialsamplesof the leaf oil of pimerna racenlos(r Based on the previous study by Tucker et al., it seemsas if
\liller) J. Moore var.rocerrlosausing both GC nnd GCIMS. this oil w:rs produced frorn leavesharvesteclfrorn trees of
Tire coruponentsthat r.vereidentilied r,vereas follolvs: di{1'erentvarieties.
Also in 1995, Abaul et al. examined the composition oi
a-thujene(0-<0.1%) 3-phenyl-2-propenal (0-0.11%) three oils produced from P racenlosavar. rac.,-liosathat
cr-pinene(O.46-0.47%) geraniol(0-0.12o/")
camphene(0-0.14%) possessedclifferent aroniatic properties. Using GC/MS as
geranial(O-0.22%)
sabinen e(0-<0.0 1% ) u-cubebene(0-<0.01%) their method of analysis,the authorsr,vereable io character-
1-octen-3-ol (0-1.74%) eugenol (44-41-68.93%) ize the differences among the tlpical clove-scenteclba_voil
3-pinene(0-0.09%) cx,-copaene (0.32-0.41%) and the lemon-scentedand anise-scentedtr,pes.The .ei.rlts
3-octanone (0-1.10%) B-elemene (0-0.20%) of'these anal_vses can be seen in Table XV. These results
myrcen e(0 .10 -16 .17 % ) methyleugenol(0-11.88%)
3-octanol(0-0.84%) confirm the earlier {indings of McHale et al. (1g77).
ct-gurjunene (0-0.13%)
u-phellandrene (0.07-0.45%) e (0.64-7 .24%) More recentll',Ayedounet:rl. (19g6)used GC and GC/
B-caryophyllen
s-terpinene (0.02-0. 19%) 0-amorphene (0-0.39%) MS to determine that a bay oii procluceclfrorn p racetllosa
&-p-dimethylstyrene aromadendrene (0-0.09%) grorvn in Benin possesseda tlpical compositionthat can be
(0-0.30%) t x - hum ulene
( 0. 15- 1. 31% ) sumrnarizedas fbllows:
lrmonene(2.07-3.90%) a llo-aromadendrene
1. 8-cine ole
(1 .38 -1.3 9%) (o-0.28%) cr-thujene (0.2%) l i n a l o o(l1 . 9 %)
(Z)-B-ocimene (0.08-0.1 0%) (0-<0.01%) 1-octen-3-o ( 1l . 6 %) borneol(0.8%)
B-cadinene
(E)-B-ocimene (0.08-1 .42%) B-chamigrene (0-O.17%) myrcene(26.6%) p-cymen-B-ol (0.6%)
1terpinene(<0.01-0.16%) B-selinene (0-0.33%) o-phellandrene (0.7%) u{erpineol(0.3%)
ierpinolene(0.09-0.24/") cr-selinene (0-0.63%) 6-3-carene (0.2%) chavicol(6.3%)
p-cymene(<0.01-0.97%) rx-muurolene (0,.O.05%) l i m o n e n e( 3 . 1 %) eugenol(52.7%)
;rnalool(0.13-3.63%) a-farnesene*(0-0.59%) 1, 8 - c i n e o l(e1 . 3 %) isoeugenol- (0.3%)
camphor(0-<0.0 1% ) T-cadinene (0.05-0. 15%) (Z)-B-ocimene (0.3%) o-cadinene(0.5%)
terpinen-4-ol (0.05-0.90%) cls-calamenene (E)-B-ocimene (0.2%) eugenylacetate(0.2%)
c-cymen-B-ol (0-<0.01 %) (<0.01-o.oy%) p-cymene(0.5%) T-cadinol(0.2%)
s-terpineol (0.14-0.52o/") 6-cadinene(0.28-1.03%)
Tethylchavicol(0.03-0.05%) "correct isomer not identified
eugenylacetate(0-0.51%)
chavico(<0.0
l 1
-15 "5 1% ) spathulenol(0-0.12%)
 D. McHale, W. A. Laurie and M. A. Woof, Composition of West
Table XV. Comparative chemical composition (%) of Indianbay oils.Food Chem.,2,19-25 (1977).
three different odor-types of Pl'menfa racemosa A. Tucker, M. J. Maciarello,R. P. Adams, L. R. Landrum and T. A.
Zanoni,V olatil,eleaf oils of Caribbean My rt aceae7. Three aarieties
Clove- Lemon- Anise- of Pimenta racemnsa (Miller) J. Mo ore of the D ominican Republic
Compound scented scented scented andthecommercialbay oil.J.Essent.Oil Res.,3,323-329 (f 99I).

cr-pinene - 0.5 0.2 A. Bello, M. L. Rodriqrez, A. Rosado and J. A. Prno, Chemical

3-octantol 2.O 0.7 0.2 composition of the leaf oil of Pimenta racerlosa (Mill. ) J. Moore
(1995).
6-methyl-5-hepten-2-one - 0.3 from Western Cuba. J. Essent. Oil. Res., 7, 423-424
3-octanone 1.0 j. Abaul, P. Bourgeoisand J. M. Bessiere,Chemicalcom:positionnJ'
4.6 12.8 the essentialoils of chemotypes of Pinxentaracenlo sa Dar. racerns a
myrcene 6.4
(P. Miller) J. W. Moore (,Boisd' lnfu) of Guadeloupe (F.W.L).
2,3-dihydro-1
,8-cineole - 0.1
- 0.2 0.3 Flav. Fragr.I., 10,319-321(1995).
o,-phellandrene
p-cymene 0.3 0.5 0. 1 A. M. Ayedoun, B. S. Adeoit, ]. Setondji,C. Menut, G. Lamaty and

1,8 -cin eo le 1. 2 J. M. Bessiere, Aromatic plants from tropical West Africa. IY.
Chemical composition of leaf oil of Pimento racernsa (Miller) J.
limonene 0.8 5.3 2.7
W. Moore oar. racemosafromBenin.I. Essent.Oil Res.,8, 207-
(Z)-B-ocimene 0.1
209 (1996).
(E)-B-ocimene - 0.4 O.4

lterpinene 0.1
frans-linalool
oxide+ 0.1
terpinolene 0.1
linalool 6.0 4.1 6.0
o,-thujone 0.1
chrysanthenone - - 1"6
ca mph or 1.5
o-cyclocitral - O-2
verbenol* 1.2 - 0.4
p-cymen-B-ol 0.1
d-terpineol 0.5 - 0.1
methylchavlcol 0.1 0.2 32.8
nerol - 0.7
ne ral 0. 1 31. 7
geraniol 0.2 3.5
chavicol 17.1 - 0.8
geranial 0.3 40.3
(E)-anethole 0.2
nericacid - 0.1
geranicacid - 1.0
eu ge no l 56. 1 0. 1 1.0
o(-copaene 0.4 0.9
methyleugenol 1.4 0.8 48.1
B-caryophyllene 0.6 0.1
o,-humulene 0.2
germacreneD 0.3
/ F F \-n -fa rn cse n e 0- 2
calamenene* 0.2
6-cadinene 0 .8
caryophylleneoxide 0 .1
q,-cadinol 0.2
* correctisomernot identified
t furanoidform
 Progress in Essential Oils
Reprinted
fromPerfumer
& Flavorist, 1998,Vol.23, No.1, p. 39
JanuarylFebruary

Sp a nis h S age O il In 1993, Fournier et al. used GC and GC/MS to analvze

In 1983,Cordoba Rodriguezexarninedthe chemicalcompo- eight comrnercial samples of Spanish sage oil. The c.ornpo-
sition of' Spanish sage oil produced frorn more than 30 nents identified in seven of these oils u'ere :rs follows:
collections of plants from different areas in Spain. She s-thujene(0.1-0.40/") linalool(1.2-2.6%)
cleteminecl that the oils possessedthe fcrllowingcomposi- cx,-pinene (4.7-8.O%) linalylacetate(0.8-3.5%)
:ional range: c a m p h e n e ( 5 . 9 - 1 3 . 4 %) b o r n y t a c e t a t e ( o . S - i.B% )
B-pinene(2.8-6.7%) B-caryophytten e (0.7-1.4%)
tr cyclene(0-0.5%) borneol(1.5-6.4%) sabinene(O.7-2.4%) terpinen-4-ol (0.4-01%)
o-thujene(0.2-0.5%) isoborneol (0.2-1.9%) myrcene(1.3-5.1%) sabinylacetate+ p7-3.9%)
cr-pinene (4.7-103%) terpinen-4-ol(0.2-0.8%) limonene(4.4-4.9%) o{erpineol(0.6-12.7%)
cam ph en e(4.6 -10 .6%) Dterpineol(0-0.7o/o) 1,8-cineole (19.8-26.9%) borneot(0.5-1.2%)
sabinene(0.6-2.2o/o) aterpineol(0.1-1.9%) yterpinene(0.1-0"9%) or-terpinylacetate(2.3,5.6%)
B-pinene(3.3-7.3%) nerol(0-0.6%) p-cymene(0.6-2.4%) geraniol(0.1-0.4%)
myrcene(1.0-4.9%) geraniol(0.1-0.7%) t e r p i n o l e n e ( 0 . 1 - 0 . 4 %) c a r y o p h y l l e n e o x i d e( 0 .1 - 0 .5 % )
c-pheIlandrene(0-0.2%) linalylacetate(0.1-5.8%) camphor(14.4-35.9%)
(x-terpinene (0-0.1%) nar\/l e^6+.+a /n 1ol^\

p-cymene(0.4-2.17o) geranylacetate(0.1-02%) + c/s-isomer,although not determined by authors

limonene(2.4-5.0o/o) bornylacetate(0.8-4.9'/.)
(Z)-B-ocimene (o-2.2%)
The other oil, rvhich probably originated fl'orr-rS.
cls-sabinylacetate(0.1-6.6%)
(E)-B-ocimene (0-0.4%) cr-cubebene(0-0.2'/") IcLa
andul aefoli a s sp,oellerea, was found to possess th e fbllorv-
t"terpinene(0-0.7%) o-copaene(0-0.1%) lng composrtion:
terpinolene (0-0.3%) o-gurjunene (O-O.2%)
(Z)-allo-ocimene. o-thujene(0.1%) l i n a l o o(l1 . 6 %)
cls-a-bergamotene (0-0.8%)
(0-0.3%) o-pinene(4.5%) linalylacetate(1.1%)
isocaryophyllene (0-0.8%)
(I-p-dimethylstyrene camphene(5.7%) bornylacetate(1.1%)
B-caryophyl Iene (0.2-3.7 %)
(o-o.4o/") B-pinene ( 3 . 1 %) B-caryophyllene (0.8%)
( 0- 1. 0% )
c r - hum ulene
s a b i n e n e( 1. 1%) terpinen-4-ol (0.5%)
1,8-cineole (12.0-40.3%) aromadendren e (0-0.2ok)
m y r c e n e( 1 . 6 %) cls-sabinyl acetate**(12.8%)
camphor(12.9-36.1%) allo-aromadendrene (0-0.4%)
limonene(4.1ol.) o,-terpineol (0.4%)
carvone(0-0.3%) ar-curcumene (0.1-0.9%) '1,8-ci neole(15.2o/") borneol(0.8%)
frans-sabinene hydrate B-bisabolene(0-0.2'/") y-terpinene (0.1%) cx-terpinyl acetate(5.8%)
(0.1 -0.6 % ) caryophyllene oxide(0.1%)
p-cymene(1.1%) geraniol(0.2%)
linaloo(0.2
l -11 .2% )
terpinolene (0.1%) caryophyllene oxide(0.2%)
c a m p h o r( 3 3 . 1 %)

Sixyearslater, an ISO document gavethe compositionof .. cls--

added by reviewer
Spanishsageoil as:
The authors pointed out tliat care must be taken in
o-pinen e(4.0 -11 .0%) B{hujone(<0.5%) selecting Spanish sage oils that contain only lorv levels of
sabine ne(0 .1-3 .0% ) linalool(0.5-0.9%) (cls)sabinylacetate becausethey have alreadl, shorvn that
limonene(2.0-5.0%) bor neol( 1. 0- 8. 0% )
this compound has potential toxicity (Pageset al. 1992).
1,8- cin eo le
(11.O-25 .0% ) terpinen-4-ol (<2.0%)
camph or(1 1.0 -36 .0%) linalylacetate(<0.5%) in 1995, Guillen and Ibargoitia compared the chernical
o{hujone (<0.5%) cornpositionof the essentialoil ofr,vild-growingSpanishsage
collected in the vicinity of Zaragoza(Aragon, Sp:rin)rvith
Using a combinationof GC and GC/M S,Zani et al.( 199I )
extractsof the samecollectedmaterial madervitlr avarietv of
reported that an oil of Saluia lauanclulaefolia,which was
solvents.The results of their GC/MS analvsesare ibuncl in
produced from ltalian-gro\vn plant rnarterial,u'as fbuncl to
Table l.
contain the fbllorving constituents:
4. Ayearlater, Guillen et al. (1996)analyzedan oil of Spanish
c-pinene(3.85%) a{hujone (3.21%) sage that was produced from plants grown in the Aragon
camphene(5.14%) Bthujone(0"61%) region of northeast Spain. Plants were mechanically har-
B-pinene(6.93%) camphor(12.25o/o)
vested lvhen they uzere in full flower and the oil that lr'as
myrcene(0.79%) borneol(3.'15%)
6-3-carene (1.19%) o-terpineol(1.36%) produced rvasanalyzedby both GC and GCI/N4S. The corn-
limonene(3.48%) p-caryophyllene (3.55%) pounds identified in the oil rvere:
1,B -cin eo le
(3 0"61 % ) s - hum ulene( 6. 10% )

171
 Tabfe f. Comparative chemical composition (o/o)of an oil of Spanish sage with various Spanish sage extracts

Compound I 2 3 4 5 Compound 1 23 4 5
tricyclene I 0 .1 0 .6 I I B-cadinene 0.1 0.1 0.3 0. 1 0. 1
cx,-thujene I 0 .4 0 .1 I I aromadendrene 0.1 0.3 0.2 o. 4 0. 4
cx,-prnene 0. 1 3 .0 3 .1 I 0.3 s-humulene 1.1 1.0 0.8 2. 0
camphene 0. 2 5 .5 I 1.3 bornylbutyrate I t 0.1 0. 1 I

B-pinene 0 .1 1 .8 1. 4 0. 1 0.9 allo-aromadendrene 0.1 0.2 0. 2 0. 2

myrcene 0 .4 1 .8 1. 5 0. 7 1.4 y-selinene t 0.6 0.3 0. 7 0. 5
p-cymene 0 .5 1.1 1. 2 1. 0 1.3 geranylpropionate t I 0.2 11
lrmonene 0 .5 t 2. 3 1. 3 1.9 ar-curcumene 0.1 0.5 0.3 0.8 0. 6
'1,8-cineole 7.7 12.1 9. 2 7. 9 10.1 0-muurolene 0.1 0.3 0.2 0.2 0.3
yterpinene 0 .1 0 .2 0. 2 0. 1 0.2 y-cadinene 0.2 1.0 0.6 0.9 0. 8
cls-sabinenehydrate 0 .1 t t 0.5 0.7 3-ethenyl-3-methyl-
linalool 0 .4 0 .1 0. 1 0. 3 0.3 2(1-methylethenyl)-
campnor 34.5 23.0 18.7 25.2 24.0
cyclohexanol 0.2 0.1 0.1 0.2 0.5
isoborneol r 0 .1 0. 4 t 0.2 6-cadinene 0.5 1.8 1.2 1. 6 1. 4
borneol 22.5 8.3 9.2 14.5 10.5 geranylbutyrate I 0.1 t 0.1 t
terpinen-4-ol 2 .4 0 .9 0. 4 1. 6 1.0 spathulenol 0.2 0.2 0.1 0.2 0. 3
viridiflorol 3.7 2.8 4.6 4. 9
c-terpineol 6 .8 3 .0 1. 4 4. 6 3.6 ^a

myrtenol 0 .1 0 .1 t 0. 1 0.1 geranylvalerate 0.1 0.1 0.1 0.2 0. 3

bornylformate 0 .3 t tt 0.1 B-eudesmol 0.3 0.4 0.3 0.3 0. 4
trans-carveol 0 .3 0 .1 ii 0.1 (r-cadinol 0.2 0.3 0.1 0.1 0. 3
heptacosane 0.1 0.2 - 0. 1
c/s-carveol 0 .1 t tt t
caryone 0 .2 t 0 .1 0 .1 0.1 octracosane 0.1 0.1 -t

geranrol 0 .8 0 .3 0.2 0.2 0.4 ethylhexacosane- 3.0 0.1 -t

geranral 0 .2 t tt I nonacosane t.z 1.1 _ n1

t
triacontane o.2 0.2 -I
isobornylacetate 0 .1 IT t
bornylacetate 1 .3 1 .4 0 .7 1 .B 1.4 ethyloctacosane* 0.2 0.2 _I
thymol 0 .1 0 .1 t 0 .1 0.1 henitriacontane 1.7 t.J
carvacrol o .2 0 .1 t 0 .1 0.1 methyltriacontane* 0.1 0.2 -t
0 .2 tt
dotriacontane 0.3 0.5 -t
ninariiannna 0 .5 I
eugenol 0 .1 0 .1 tt I ethyltriacontane- 0.4 0.5 -T
o(-copaene t 0 .5 0 .3 0 .5 0.4 tritriacontane 2.8 3.2 - 0. 1
bornylpropionate 0 .5 0 .3 0 .3 0 .6 0.8 methyldotriacontane- 0.2 0.2 -I

geranylacetate
tetratriacontane 0.2 0.2 _I
0 .1 0 .1 1I 0" 1
cls-jasmone 0 .1 0 .1 tt 0.1 pentatriacontane 0.3 0.3
s-gurJUnene 0 .1 0 .3 0 ,2 0 .3 0.3
B-caryophyllene u.J t.o 0.9 2.4 2.6

-c o r r e c t i s o m e r n o t i d e n tifie d ;1 = e sse n tia lo il;2 = p e n ta n e extract;3=mel hyl enechl ori deextract;4=methanol extract;5=acetoneextrac t;l = trac e

tricyclene(0.20%) (0.50%)
cx,{erpineol ar-curcumene (0.01%) 3-ethenyl-3-methyl-2-
0,-thujene(0.30%) bornane-2,3-diol+(0.13%) ledene(0.51olo) (1-methylethenyl)-6-
o-pinene(7.02%) bornylacetate(0.96%) s-muurolene(0.28'/.) (1-methylethyl)cyclohexanol**
camphene(4.53%) bornylpropionate (0.10%) "y-cadinene
(0.92%) ( 0 . 1 0 %)
sabinene(3.77%) cx-cubebene (0.23o/") 8-cadinene(1.7$o/o) viridiflorol(0.43%)
myrcene(5.80%) a-yfangene(0.04%) cadina-1,4-diene(0.06%) fonenolt(0.41%)
s-terpinene(1.83%) d-copaene(0.68%)
p-cymene(3.60%) B-cubebene (0.11%) t identification
requiresfurtherspectroscopic
corroboration
y-terpinene(1.08%) o-gurjunene (0.74%) " incorrect perreviewer
identification.
terpinolene (0.33%) B-caryophyllene (5.58%)
1,8-cineole(12.82%) (0.21'/.\ The existence of q,- and B-thujone as components of
B-cadinene
cis-sabinenehydrate (0.41o/") clovenetgA7"/") Spanishsageoil is unusual,so the oil analyzedby Guillen et
cr-thujone(11.07%) aromade-ndrene (0.54%) al. must be consideredatlpical. In addition, the constituents
B-thujone(2.89%) sativenet(0.10%) listed with "o*" are not normally found in essential oils;
camphor(15.89%) cr-humu{qne (4.17"/")
therefore, their natural occurrencein this oil is questioned
pinocamphone (0.08%) farnesen-e*(0.15olo)
borneol(3.39'/") cadinene.(0.29%)
by this reviewer.
isopinocamphone (0.05olo) y-selinene(0.30%) The following year,Boelens(1997)reported the resultsof
terpinen-4-ol(0.33%) selinene*(0.38%) the analysesof Spanishsageoil for the period 1990-1995.
The compounds identified in the oils and their quantit:rtive G. Fournier, N. Pagesand I. Cosperic,Contributiontothe shtdy oJ
range can be seen as follows: Salaia laaandulifolia essentia[oil: potential toxicity attributible
to subinyl acetate.Planta Med., 59, 96-97 (1993).
tncyclene(0.2-0.3o/o) fenchol"(0.1-0.2%)
u-thujene(0.2-0.3%) sabinol-(1.5-2.5%) M. D. Guillen and M. L. Ibargoitia, Wilcl grouing Spanish sageas
<x-pinene (6.5-8.1%) camphor(13.5-20.0%) a rna^meteriol in tlrcfoocl inchtstry. Studtl by gaschronato graphq/
camphene(4.3-6.6%) borneol(1.1-2.3o/o) mass spectrone.try of its e,s,sentirLl oil and extracts in sexercLl
sabinene(1.7-21%) terpinen-4-ol(0.5-0.6%) organicsoloenfs.Chem. Mikrobiol. Technol. Lebensmitt., 17(5/
B-pinene(3.8-4.5%) a-terpineol(1.0-1.3%) 6), 129-r34 (1995).
myrcene(4.1-5.0%) nerol(0.1-0.2%) M. D. Guillen, N. Cabo and ]. Burillo, Characterization of the
a-phellandrene (0.1%) neral(0.1-0.2%) es,sentialoils of some cultirated aromatic plant,s of industrial
6-3-carene (0.1olo) geraniol(0.3-0.5%) intere,\t.J. Sci. Food Agric., 70, 359-363(1996).
s-terpinene(0.2-0.3./") geranial(0.1-0.3%)
M. H. Boelensand H. Boelens,Chenticalandsensoryeaaluationof
p-cymene(0.6-1.3%) linalylacetate(3.0-6.0%)
three sageoils. Perfum. Flavor., 22(2),19-10 Ql;97).
limonene(3.0-4.5%) bornylacetate(1.0-3.0%)
(Z)-p-ocimene (0.6-0.8%) sabinylacetate.(1.8-62%) B. M. Lawrence, unpublished information (1997).
(E)-B-ocimene(0.2-0.3%) acetate(9.5-11.0%)
cr-terpinyl
J-terpinene (0"3-0.8%) nerylacetate(0.1-0.2/") Thyme Oi l
terpinolene (0.2-0.4%) geranylacetate(0.4-0.7%)
1.8-cineole (19.0-21.0o/o)
In 1989, Mookherjee et al. used GC/MS to compare the
cls-cr-bergamotene (<0.1%)
trans-sabinene hydrate B-caryophyllene (O.7-1.2%) chemical compositionfrom the dlnamic headspaceanalysis
(0.1 -0.2 % ) cr-humulene (0.4-11%) o{'living and harvested Thyruts aulgaris with that of a
cls-sabinenehydrate B-bisabolene(0.2-0.3o/o) commercial thyme oil. Since most of the commerical thyme
(0.2-0.4%) 8-cadinene (0.1-0.2%) oil originate s fr om Thy mu s zy gis, this direct comparison may
linalool(1.4-2.7%) caryophyllene oxide(0.1-0.2%)
not be of much value.The resultsof this studv can be seenin
- correct ,somer not identified Table tI.
-\lso, Lawrence (1997)examineda cornmercialsampleof The following year,Kreis et al. (1990)used enantiomeric
jlranish sageoil. Using a combination o{ modern analltical separationon a chiral capillaryGC column to determine that
.=chniquesthe oil was found to contain: the enantiomericratiosof u-pinene, 0-pinene and limonene
in T. oulgrLri:soil were as follows:
u-thujene(0.25%) linalool(2.98o/o)
cr-pinene(6.40'/") u-gurjunene (0.01%) (S)-(-)-o-pinene(89%): (R)-(+)-cr-pinene
(11%)
3amphene(6.25%) linalylacetate(1.33%) (S)-(-)-0-pi
nene(e6%): (R)-(+)-B-pine
ne (4%)
3-pinene(4.32%) cls-0-bergamotene (t)
(S)-(-)-limonen
e (70%): (R)-(+)-limonene
(30%)
sabinene(1.54%) bornylacetate(0.56%)
Tyrcene(1.51%) frans-o-bergamotene (t) In 1992,Jeanet al. comparedthe chemicalcompositionof
monene(4.25%) terpinen-4-ol (0.4270) an oil of thyme (ex. Z oulgaris) produced by hydrodiffusion
' .8-cineole (24.30o/") B-caryophyllen e (0.42ok)
r,vith microwave extracts of thvme produced in different
Z)-B-ocimene (0.16%) aromadendrene(t)
E )- B-o cime ne
(0.1 5%) cls-sabinylacetate(5.05%) solvents. The conditions used for the microwave extract
i.':erpinene(0.02%) allo-aromadendrene (t) preparation were as follows: 15 g of fresh thyme placed in
3-cymene(1.20%) borneol(0.30%) a beaker containing 150 mL of organic solvent (toluene,
::rcinolene(0.03%) o,-humulene (0.05%) carbon tetrachloride or hexane).This beaker \^/asplaced in
Z.Z)-allo-ocimene (0.06%) cls-sabinol (O.21%)
:-o-dimethylstyrene (0.039.) o-terpineol (0.05%)
:ans-sabinenehydrate 6-cadinene (0.30%)
Table ll. Comparativechemical composition (%)
r0.1 4% ) ar-curcumene (0.03%)
of the dynamic headspaceof living and harvested
,r-cubebene(t) nerol(0.01%)
Thymus vulgaris plants and a commercial sample
-1-.opaene(t) geranjol(0.52%)
of thyme oil
:arphor (26.40%) viridiflorol (0.36o/o)
= : ' ace (< 0 .0 1%)
Living Harvested
Compound plant plant Oil
-i; los Angelos Cordoba Rodriguez, Contribucitn nl estutho
l.!. -\ceite Esencinlde Salaia E,sponola(Sahialaaancla,laefolia (E)-2-hexenal
r, r:/r1 PhD thesis,Univ. Compiutense,Madrid, Spain (1983). 2.8
2,4-hexadienal" 0.1
, . Oils of Sponish Sage (Saloia laaunthrlaefolia). ISO,ICS\ (Z)-3-hexenylacetate ti.z 0.1
\1555. ISO Public.Lisbon,Portugal(1989). 1-octen-3-ol 8,2 8.0
Z,rri. G. Nlassimo,S. Benvenuti, A. Bianchi, A. Albasini, M. p-cymene 30.0 50.0 30.0
\frleqari, G. Vampa, A. Bellotti and P. lfazza, Stud.iesonthe limonene 1.3 1.1 1 .7
..'r.rforlc propertie,s of essential oils uith Bacillus subbilis methylthymol 1.3
-., - c ssay anrl sohrutnella/tnicrosorLereuersionassay.Planta M ecl., methylcarvacrol t.3 0 .1
5: lrl;-14 | / t9 9 l).
., thymol 15.2 9.0 39.7
:-.:es. G. Fournier, V. Velut and C. Intberk, Potential terato-
carvacrol t.J 0.9 1 .0
. ,ltity in mice of the essentialoil of Sahia lauandulifoliaVahl
: -..fu o.fafraction rich in sabinyl acetare.Phyother. Res.,6(2), - correctisomernot identified
r -Sl 19 92 ).
 This sampleof thyme oil was found to exhibit the greatest
Table lll. Comparativechemicalcomposition (%) inhibition of growth againstall organismstested, while the
of thyme oil and extracts antioxidant activity was moderate. The authors attributed
the antimicrobial activity to the three major oil components.
Hydro- Not surprisingly,the authors viewed thymol as being the
diffused Toluene CCl4 Hexane
Compound oil extract extract extract most efI'ective.
An oil of T. aulgaris that was produced for two separate
o-thujene 0.40 0. 18 0. 80 t
a- prn en e 0. 17 t 0.34 t seasonsin Casolavalsenio, Italy, was subjectedto analysisby
B-pinene 0.07 0. 17 0. 23 r a combination of GC and GC/MS (Piccagliaand Marotti,
4,7-dimethyl-4-octanolt 0.69 0.44 0.82 0.89 1993).The compounds that were characterizedduring this
0.46
6-methyl-5-hepten-2-one 0. 40 1. 42 1.44 analysiswere:
myrcene 1.03 o. 27 1. 05 t 0-thujene (0.87-2.10%) methylthymol(1.43-1 .52%)
3-octanol 0.20 t 1. 11 0.92 nene(0.49- 1.34/")
cr-pi thymoquinone(trace)
o,-phellandrene 0.05 0. 27 0. 14 t camphene(0.18-0.46%) bornylacetate(0.04-0.07%)
crterpinene 0.56 0"20 0.37 t sabinene(t) thymol(16.55-38.24%)
o/o)
p-cymene 2.23 1. 14 2. 91 0.95 B-pinene (0.17 -0.41 carvacrol(0.61-1.72%)
limonene+ B-phellan- 1-octen-3-ol(0.41-0.67%) cuminalcohol(t-0.08%)
drene 0.23 t myrcene(1.40-2.14%) ct-copaene(t)
cr-phellandrene (0.15-0.19","/ B-bourbonene (t)
1,8-cineole t 1. 18 r
6-3-carene(0.07-0.13%) B-caryophyl lene (2.38-4.28%)
(Z)-B-ocimene i.t 0. 17 0. 43 t
o-terpinene (1.67-2.34%) B-gurjunene (t-0.04%)
(E)-B-ocimene 0.46 0. 55 t t p-cymene(18.60-25.34%) aromadendrene(t)
T-terpinene 4.47 2.89 7.72 2.45 (0.13-0.23%)
limonene(0.17-0.30%) cr-humulene
frans-sabinenehydrate 0. 25 0. 42 1,8-cineole (1.96-2.62%) (Z)-B{arnesene (trace-0.04ol.)
terpinolene 0. 84 t - yterpinene(12.06-12.27%) cr-muurolene (0.04-0.07%)
linalool ).tt 8. 65 1. 35 5.76 terpinolene (0.18-0.19%) viridiflorene(t-0.10%)
terpinen-4-ol 1. 29 r - linalool (2.42-2.82%) "y-muu rolene(t-0.08%)
cr-thujone (0-0.51%) y-cadinene (0.06-0.15%)
carvone 1 .0 2 0.62 0.75 t
Blhujone(0-0.15%) 6-cadinene (0.11-0.25%)
geraniol 1 .0 2 - 1. 23 2.61
42.50 50.54 14.02 23.17 camphor(t-0.30%) caryophylleneoxide
linalylacetate
borneol(0.44-0.45%) (0.29-0.45%)
bornylacetate 0. 66
terpinen-4-ol (0.98-1.10%) 6-cadinol(t-0.09%)
thymol 9.35 6. 28 31. 29 43.10 p-cymen-8-ol(t) cr-cadinol(t-0.05%)
carvacrol 5.07 5. 25 10. 92 6.96 cr{erpineol(0.17-0.260/0)
d-copaene 0 .0 9 0. 26 0. 54 2.10
B-caryophyllene 3.56 3. 10 2. 67 r
cx,-humulene 0 .1 2 0. 16 t - A year later, Moldao-Maftins et al. (1994) compared the
+ doubtlulidentification sensoryaspectsand chemical composition of oils produced
t = t r a c e( < 0 . 0 1 % ) by steam distillation and hydrodistillation with that of the
N, flushed headspaceof T. zygis ssp.syloestri.scollected
from the north of Portueal. The authors found that the oils
a conventional microwave oven (750W 2450 MHz) for not possesseda similar qualitative composition, although they
rnorethan 60 s.After filtration. the solventwasconcentrated did not presentanyuseful quantitativedata.The compounds
by a factor of 15 in a rotary film evaporator, at which time it identified in the oils were as follows:
was ready for GC analysis.The comparativecomposition of 0-thujene borneol
the oil and extractscan be seenin Table III. It is worth noting tX-prnene terpinen-4-ol
that extractsproduced in a microwave transparent solvent campnene hexylbutyrate
are clear and only lightly colored, whereas those produced F-pinene nerol
myrcene neral
from polar solventsare opaque and ofdark green color. The geraniol
cx,-phelland
rene
color originates from the chlorophyll in the leaf. Chlorophyll ct'-terpinene linalylacetate
causesthese extractsto have a shortened shelflife because lrmonene bornylacetate
chlorophyll is a UV potentiator for oxidativereactions. p-cymene thymol
The following year, a sample of lab-distilled thyme oil
1R-ninanla carvacrol
Y-terprnene geranylacetate
produced fromT. aulgariswas screenedfor its antimicrobial
octanol B-caryophyllene
and antioxidant activityagainst25 strajnsofbacteria (Piccaglia terpinen-1-ol dodecanal
et al. 1993). The oil used possessedthe following major unoecane cx-humulene
co m ponent s : ,r linalool caryophyllene oxide
campnor tetradecanal
p-cymene (19-25%)
thymol(17-38% For readers who presume that these oils were rich in
y-terpinene
(12-13%) thymol (aswasthe preiumption of this reviewer),the authors
noted that the level of p-cymene and y-terpinene was only the thymol chemotype of T. zy gis ssp.gracilis is f,pical
directly related to a preference for the oil. They found that of the red thyme oil of commerce.
the steam-distilled oil, which had the lower levels of Also in 7995,ZygadIoet al. screeneda few essentialoils
p-c).rneneandy-telpinene, waspreferred to the hydrodistilled for their antioxidant properties. They showed that an oil
oil, The headspacewas found to have an unacceptable of thyme (ex. T. aulgaris) exhibited significant antioxidant
odor becauseit was rich in monoterpenehydrocarbons,with activity.The major constituentsof this oil were:
p-cymene and y-terpinene being the major components. o-pinene(2.6%) (10.1%)
T-terpinene
Variations in the chemical composition of the essential camphene (2.7o/o) p-cymene(1"0%)
oils of T. zygis L. ssp.syloestri,s(Hoffm. et Link) Brot. ex. B-pinene(4.2%) linalool (2.2'k)
Coutinho and T. zygis L. ssp. gracilis (Boiss.) R. Morales myrcene(4.3%) carvacrol(15.0%)
limonene(3.4%) thymol(30.3'l")
from southeasternSpain were determined by S6ez(1995).
In this study, oils from four collections of each subspecies Raghavenet al. (1995) compared the hydrodistilled oils
s'ere examinedby GC and GC/MS. A summary of the data of Indian thyme (ex. T. oulgari.s)produced both from fresh
obtained from these analyses(Table IV) showsthat diff'erent plants and those dried under a variety of conditions. The
chemotlpes of eachofthe subspeciescanbe found. Ofthese, composition of these oils, which were analyzed by GC

Table lV. Chemicalcomposition (%) of various chemotypesfound among the oils

ol Thymus zygisssp. gracilis and L zygisssp. sylvestris

T. zygis ssp. gracilis T. zygis ssp. sylvesf,,rs

Compound 1 2 3 4 5 6 7 I
c-thujene 0 .0 1 0.04 3.23 0.08 0.44 1 .2 7
a-pinene 0.04 4.77 0.10 0.89 0.24 2.28 0.73
campnene 0.30 0.49 0.12 I AA
3.58 1.76 0.06 0 .1 6
B-pinene 0.04 0.34 0.04 0"18 2.25 0.29 0.66 0.07
sabinene 0.05 0.05 0.02 0.06 0.19 1 .2 2
myrcene 0.08 3 .1 4 0.08 0.85 1.72 0.09 0.20 1 .6 7
cr-terpinene 0.02 0.07 0.86 0.24 1.91 0.03 0.34
limonene 0.09 3.40 o.oo 0.37 18.97 0.13 0 .2 1
'1,8-cineole 1. O 2 0.08 0.11 0.26 34.50 .FA to. tJ 0,o2
(Z)-B-ocimene t. t+ 0.28
fterpinene 0.36 0 .1 5 0.26 o.J+ 1.52 10.95 0.1B 1 0 .8 9
p-cymene z- v3 13.44 0.32 1B.BO 6.69 27.63 o.24 28.15
terpinolene 0.04 0.04 0.08 0.79 0 . 15 0 .1 0
trans-sabinene
hydrate o.tu 1 .3 4 0.04 0.26 0.37 v .z z 1.71 0.56
campnor 0.56 0 .1 1 0.07 0.27 0.19 0.10 1.35 0.82
linalool 7.89 28.64 91.40 1.13 6.75 5.10 72.95 3.56
Iinalylacetate 0.06 t.oJ 0.68 0.16 0.07 0.40 0.52 0.04
isobornylacetate 1. 17 0.40 0.08 0.68 0.99 1.04 0.36 0.34
terpinen-4-ol 1. 60 1 7 .0 2 0.22 0.05 0.24 1.15 0.03 2.27
p-caryophyllene 0-12 0 .t8 0.54 1.86 0.36 0.28 0.03
&terpineol 0. 11 0.40 0.03 0.85 nee 0.03 0.40 0.05
ct-terpineol 0.08 0.47 U .U 3 1.07 0.04 0.02 0 .2 1
oorneol | .oJ 2.38 o-75 3.86 4.06 1.04 1 .0 5
geranylacetate 0.09 0.07 0.04 5.20 0.16 0.24 0.02 0.04
citronellol 0.08 0 .1 2 0.15 0.20 0.13 0.06 0.08 0 .1 2
g€raniol 0 .1 4 0 .7 1 0.26 u. t3 0.30 0.39 0.05 0.23
caryophylleneoxide o.07 0.77 0.17 0.51 0.55 0.63 0.20 1 .2 9
viridiflorol 0 .0 8 0.80 0.04 0.06 0.11 0.05
elemol 0.08 0.24 0.27 0.04 0.01 0 .1 0
spathulenol 0.28 a 0.48 0.o7 i.,o 0.08 0.11 0 .1 6
!r'lymol 7 1 .8 4 0.24 0.31 25.45 T .+J ga.ra 0.02 24.39
carvacrol 3.34 ' 0j2 0.05 22.79 0.03 t.oo 0.03 18.20
cr-cadinol 0.05 0 .1 2 0.02 0.01 0.06 0.04 o.02 0.03

1= t h y m o lc h e m o t y p e2; = lin a lo o l/te r p in e n - 4ch 4=thymol /carvacrol

- o le m o typ e3; = l i nal oolchemotype; chemotype;
5=1,8-ci neol e/l i monenec hemoty pe;
i = thymolchemotype;7 = linalool/1,8-cineole chemotype;I = thymol/carvacrol chemotype
 relative component amounts shown as mg/kg calculated on a
Table V. Comparativechemical composition (%) of dryweight basis):
the oils obtained from fresh thyme and dried thyme
produced by a variety of processes (Z)-3-hexenol(t) cls-dihydrocarvoner(23 mg/kg)
tricyclene(7 mg/kg) methylchavicol(t)
o,-thujene(269 mg/kg) citronellolr(5 mg/kg)
Compound 1 4 o(-pinene(270 mg/kg) nerol(4 mg/kg)
o(-thujene 3 .6 3 .8 3 .7 3.2 camphene(168mg/kg) methylthymol(101mg/kg)
cI-pinene 0 .4 0.5 0.4 0 .3 sabinene(t) neralt(13 mg/kg)
1-octen-3-ol 1 .4 t.o t.o 1 .5 1-octen-3-ol(135 mg/kg) methylcarvacrol(84 mg/kg)
myrcene 1.0 0 .9 0 .9 0 .7 B-pinene(77 mg/kg) linalylacetatet(1 mg/kg)
myrcene(342 mg/kg) geraniol(t)
u-phellandrene o.2 0.2 0.2 0 .1 3-octanol(23 mg/kg) geranialt(t)
cx,-terpinene 1.4 1 .3 1 .3 1 .0 o-phellandrene (19 mg/kg) bornylacetate(t)
p-cymene 7. 9 1 1 .1 1 0 .1 8 .7 o.t 6-3-carene(21 mg/kg) thymol(6465 mg/kg)
lrmonene 0. 3 0 .3 0 .3 o.2 o(-terpinene(254 mg/kg) carvacrol(840 mg/kg)
y-terpinene 14.5 12.7 9 .7 0.1 p-cymene(4013 mg/kg) thymyl acetate (t)
linalool 1.0 0. 8 1 .2 limonene(62 mg/kg) eugenolr(t)
terpinen-4-ol 0.5 B-phellandrene (26 mg/kg) geranylacetate(t)
thymol 6 0. 1 59.5 60.5 64.9 a3.s 1,8-cineole(92 mg/kg) B-elemenet(t)
(Z)-B-ocimene (t) cr-iononet(t)
B-caryophyllene 4.4 (E)-B-ocimenet (t; B-caryophyllene (213 mg/kg)
bisabolene. c. l
y-terpinene(1817 mg/kg) lrans-cr,-be
rgamotene
oil y i e l d 1 . 54 1. 10 0.95 0.90 0.37 lrans-sabinenehydrate (14 mg/kg)
(275 mg/kg) o,-humulene (t)
- correctisomernot identified;1 = f resh;2 = lreezedried (-40'C and terpinolene(11 mg/kg) allo-aromadendrenet (t)
{40'C/6 h); 3 = cross-flowair dryer(40"C/11h); 4 = flow-throughair Iinalool(368 mg/kg) a-muurolene (t)
dryer(40'Cl8.5h); 5 = shadedrying(28"C/120h) crb-sabinene hydrate B-iononst(S mg/kg)
(59 mg/kg) germacrene D (16 mg/kg)
o-thujonet(13 mg/kg) Q Li^^L^t^^^
p-ur-dugrEr
/+\
rE (r.,
quantitative data) and GCiMS (component identification), isopulegolT(t) (Z)-nerolidolt(17 mg/kg)
can be seen in Table V. camphor(34 mg/kg) y-cadinene(t)
Consideringthe various methods used to dry the thyme, menthoner(t) 6-cadinene (t)
isomenthonet(t) irans-calamenene (t)
t}te authors felt that the flow-through method of drying was
isoborneol(t) (E)-nerolidolt(27 mglkg)
tle best. However, this reviewer believes that the freeze- borneol(t) y-eudesmol(t)
d+ltg method appearsto be equally good, especiallywhen terpinen-4-ol(t) farnesol-r(t)
one considersthat the oil yield of freeze-driedthyme is about p-cymen-B-ol(t) T-cadinol(t)
l[]rc higher than that of thyme dried by the flow-through oterpineol (9 mg/kg)
metlod. I tentative identification;
* correct
isomer not identified
-{n oil of Z oulgaris that was rich in thymol was found by t = trace (< 1 mg/kg)
Dorman et al. (1995) to possessstrong antioxidant activity.
These same authors determined that when the herb was
-{-soin 1995, Bourrel et al. screeneda number of essential
oil: lbr their antimicrobial properties.Among these oils was stored over a period of 10 months, quantitative changesin
an oil of I aulgaris . This oil was found by GC/M S to possess some of the volatile constituents occurred. A summary of
the following composition: these changescan be seen in Table VI, which shows that
only u-thujene, myrcene, o(-terpinene,y-terpinene, trans-
a-thujene(0.9%) B{erpineol-(5.9%) sabinene hydrate and caryophyllene oxide showed large
a-pinene(0.8%) linalool(9.6olo)
camphene(0.9%) camphor(0.9%)
changes.The interesting finding here is that all component
'l-octen-3-ol(1.2%) borneol(2.1%) amounts decreasedover the l0-month period except for
sabinene(0.5%) terpinen-4-ol(2.9%) caryophyllene oxide, which increased (almost proportion-
ftpinene (0.3%) methylthymol(1.0%) ately with the decreasein B-caryophyllene).Becausethe
myrcene(1.6%) thymol(15.8%) th).nneherb wasstoredin polyethylenebags,it is possiblethat
u-terpinene(0.6%) carvacrol(10.5%)
p-cymene(31.7%) (1.6%)
airpassingthrough the bagsassistedin this oxidation.Finally,
B-caryophyllene
1.8-cineole(2.9%) caryophyllene(0.4%) Venskutoniset al. alsodeterminedthat no significantchanges
lterpinene(3.9%) occurred in the volatiles of thvme whether it was irradiated
or not, and that the volatile composition of freeze-dried
- correcl isomer not identified
thyme was comparable to that of air-dried thyme.
Using a combinationof GC and GC/MS Venskutoniset al. Also in 1996, Delpit et al. (1996a)analyzedan oil of the
1996) examinedthe chemical compdsition of an extract of sabinenehydrate-rich clone ofZ oulgaris ofFrench origin.
thvrne produced using a Likens-Nickerson apparatus and This is the sameas one of the chemo$pes found by Granger
diethyl ether as the solvent. The compounds that they iden- and Passet(1973) more than 20 years ago. Using GC and
tified in fresh thyme (7. uulga4s) are listed as follows (with GC/MS as the methods of analysis,Delpit et al. reported
 Table Vl. Changesin volatile constituents(average Table Vll. Comparativechemical composition (%)
values in mg/kg calculatedon a dry weight basis) of a supercriticalfluid extract (SFE)and a
of thyme during storage steam-distilledoil of thyme

Storage time (months) Compound oi l SFE

Compound 0 1 5 10 B-pinene 0. 5
myrcene 0.2 1. 3
crthujene 225 179 92 54 limonene 0.3 t.o
&-ptnene 257 222 241 254 6-3-carene u.o 3 .0
myrcene 299 268 166 117
cl-terpinene 220 198 151 106 p-cymene 7.2 14.3
y{erpinene 5.2 25.0
p-cymene 3863 3694 3360 3538 linalool 2.7 0 .6
y-terpinene 1296 1173 805 410 thymol 62.5 lJ.z
trans-sabinene
hydrate 260 233 97 81
linalool 345 355 323 324 carvacrol to-J 33.3
B-caryophyllene t.J t.Y
borneol 189 160 169 183 cr-bisabolene* o4 0. 8
thymol 6912 8153 6441 6426 palmiticacid 0. 4
carvacrol 827 1027 BB0 979
t correctisomer
B-caryophyllene 283 311 303 242 not identified

caryophyllene
oxide 34 58 68 114

Although the authors did not present quantitative data

for all ofthe above-listedconstituents,they did report that
that the range in quantitative data found in oils produced
the major components o-terpineol and u-terpinyl acetate
{r'om 14 clonesof this unusual chemotype of T. oulgaris was
varied betwe en 5 -44Voand 32-78Vo,re spectively,depending
found to be as follows'
upon the season of harvest and the clone harvested
cr-pinene(1.4-2.9%) 1-octen-S-ol(0.1-0.7%) (I2 were examined). A further interesting point for the
o-thujene(0.4-1.0%) frans-sabinene hydrate readers is that both these sabinene hydrate-rich and cr-
camp he ne(0.1 -1.0% ) (36.8-49.4%)
terpineol acetate-richclones ol T. aulgaris are under study
B-pinene(0.5-0.9%) crs-sabinene hydrate(5.8-9.0%)
sabinene(1.6-2.6%) linalool(0.2-4.8%) with the idea to introduce them asnew specialtycommercial
myrcene(1.4-6.2o/0) cis-pinenehydrate..(0.2-0.85%) oils of French origin.
o-terpinene(0.3-2.0%) B-caryophyllene (0.7-3.6olo) This same yeaE Oszagyan et al. (1996) analyzed the
limonene(2.5-3.5%) terpinen-4-ol(1.8-5.7%) compositionof a supercriticalfluid CO, extractof thyme (ex.
1,8-cineole(0.5-1.2'/.) (2.6-3.8%)
cr-terpineol
y-terpinene(1.0-2.5%)
T. aulgaris) and compared it to a steam-distilled oil. The
myrcen-8-ylacetate(3.8-8.3%)
(E)-B-ocimene (0-0.1%) myrcen-8-ol(6.0-10.4%) quantitative data was obtained by analyzing the oil on a
p-cymene(0.5-1.0%) thymol(t-0.5%) capillarycolumn fitted in a GD-trID, whereasthe identity of
terpinolene(0.2-0.5'/.) each component was determined by GC/MS. A comparison
" probably a misidentilicationof cls-p-menth-2-en-1-ol between the two analysesis shown in Table VII.
t = tra ce (< 0 .1%)

It is ofinterest to seethat theseauthorscharacterizedand R. Granger,]. Passetand J. P. Girard, Methyl-2-methqlene-6-

octadiene-2,7-ol-isolede Thymusoulgaris.Phltochemistry,I 1,
confinned the presence of 2-methyl-6-methylene-octa-2, 2301-2305 (1972).
l-dienol (myrcen-8-ol) and its acetate. This confirms the
R. GrangerandJ.Passet,Thymus aulgarisspontanefu France:races
studvby Granger et al. (1972)in which this samecompound chimic1
ue,set chemotaxonotni
e. Ph1,t
o chemistry,12, I 683-I 69I
'.r'asfound in the sabinene hydrate-rich chemotype of ? (1e73).
'-'tlgaris. B. D. Mookherjee, R.A. Wilson,R.W. Trenlde,M. J.Zampinoand
In another study,the same authors (Delpit et al. 1996b) K. P.Sands,Naraclimension,s inJlautrresearch.Herbsandspices.
lso eramined the composition of a secondchemotype of Z In Flat:orchemistrytrendsanddedopment,s. Edits.,R.Teranishi,
','tlgari.s.Inthis oil theyidentified the following components: R. G. ButteryandF. Shahidi,pp. 176-187, ACS Symp.Series,
Amer.Chem.Soc.,Washington, DC (1989).
cr-thujene cls-sabinenehydrate P. Kreis,U. Hener andA. Mosandl,Chlral inhaltstffi ritherischer
u-pinene terpinolene Ole I I I. Stereod ifferen:ietu ng uon a-pinen,ft pinenund lim,onen
,R
campnene ilnatool
i tr titlrcri schetr Olen,d rogenundfeftiganneinritteln.Dert. Apoth.
sabinene oorneoL Ztg.,l3O, 985-988(1990).
3-pinene terpinen-4-ol
'nyrcene cx-terpin€ol F. I. Jean.G. J. Collin and D. Lord, Essentialoilsand microuaae
c-cymene linalylacetate extracts of cultiaateclTiants. Perfum.Flavor,f 7(3),35-4I (f 992).
monene bornylacetate R.Piccaglia, M. Marotti,E. Giovanelli,S.G. DeansandE.Eaglesham,
'.:erpinene 0-terpinylacetate Antibacterial and ontioxidant p roperties of Medit erranean
:rans-sabinene
hydrate B-caryophyllene aromaticplanfs.Indust.CropsProducts,(2),47-50(1993).
R Piccaglia and \I. Marotti, Characterization of seaeral aromatic
Table Vlll. Comparativechemicalcomposition (%)
,l.r;ritsqrtrcn irtnorthentltaly.Flav.Fragr.J.,8, 115-122(1993).
of Indian cinnamon bark and twig oils
\1, \Ioldao-\Iartins, G. Bernardo-Gil and M. L. Beirao da Costa,
-\r,.nn of Tl'tgtttuszygis chemical and sensorial annlysis' Dev.
Food. Eng., Proceedings6th Internat. CongressofEngineered Compound Bark oil Twig oil
Foods irr 1993, (f), 2L2-214 (1994). a-pinene 0.18 0.21
F. Sfez. E.ssentialoil uaritfuility of Thymus zygis grouingu;ild in limonene 0.18 0.14
t outJrc osten1 Spain. Ph1'tochemistry,40, 8f 9-825 ( 1995). 1,8-cineole 0.26 0.64
linalool 2.48 3.05
i. -\. Zrgadlo, A. L. Lamarque, D. M. Maestri and N. R. Grosso,
Entpleode aceitesesencialescomoantioxida'ntesnaturales.Crasas 0.90 O.73
B-caryophyllene
-{cietes, 46. 285-2BB( 1995). terpinen-4-ol 0.80 0.50
B. Raqhar"an,K. O. Abaham and W. D. Koller, Flauour quallty of o,-humulene 0.28 0.1I
thtlme. PAF AI, (OcVNov), 9-14 (1995) (E)-cinnamaldehyde 82.11 76.07
-freshand dried Indian
H. T.D. Dorman, S. G. Deans,R. C. Noble and P. Surai,Eoaluation (E)-cinnamyl
alcohol 7.69 9.55
in titro plant essentialoils as natural antioxidanfs. J. trssent. Oil. (E)-cinnamyl
acetate 0.95 0.43
Res.,7. 645-651(1995). coumarin 0.41 0.32
C. Bourrel, G. Vilarem, G. Michel anclA. Gaset,Et ud e despropridtds eugenol 0.76 4.03
bacteriostatiques et fongistatiques en Milieu solide de 24 lruiles
essentiellesTtrdamblementanalysdes.Rivista Ital. EPPOS, No.
16.3-12 (1995).
Four years later, Cheng and Yu (1993) reported that
F,. \-enskutonis, L. Poll and M. Larsen, Influence of drying and
irradiation on the cnmposition of uolatile compounds of thyme cinnamon bark oil produced in Yunnan contained cinna-
Tl'n1mus aulgaris L.). FIav. Fragr. J., 11, f23-f28 (1996) maldehyde (46.5Ea)and a low concentration of eugenol.
5 Delpit, J. Lamy, F. Rolland and G. Astared, Le Thgm uul-gaire Sinceno other constituentswere identified in this study,the
Thymis aulgarts L.) chimiotqpes a-teryindol - selectionclonal- reasonsfor this unusualoil compositioncannotbe proposed'
ltude chimiqua. RMsta Ital. EPPOS, (Numero Speciale),403- In 1995,Jayatilakaet al. analyzed16 samplesof cinnamon
108 (1996a).
bark and showed that the oil contained the following major
: Delpit, j. Lamy, F. Rolland,j. C. Chalchat and R. Ph.-Garry,_Le constituents:
Tlrym uulgaire (Thgmus aulgaris L.) chimiotqpe a thujanol-4-
i ction clonale - 6tude chimiqae. Rivista Ital. E PPO S, (Numero (E)-cinnamaldehyde eugenol(0.8-4.0%)
',:I
Speciale),409-416 ( 1996b). (85.0-93.0%) B-caryophyllen e (0.4-4s%)
\l Oszagyan,B. Simandi, j. Sawinsly, A. Kery, E. Lemberkovics linalool(0.3-2.5olo) 2-methoxy-(E)-cin namaldehyde
:ndJ.lekete, Supercriticalfluid eriracti..n of uolatile comytttunds (Z)-cinnamaldehyde ( 0 . 1 - 1 . 3 %)
(1996). (o.B-3.5%) benzylbenzoate(0.1- 1.2o/")
,'r'oitlat:andin andthyme. FIav. Fragr. J., f f , 157-165
In addition, minor quantities (amounts not given) of the
C i n nam on O il
following constituents were also identified in cinnanon
I". 1987,Hicks and Abdullah oxidized oils of cinnamon leaf bark oil:
;,d cinnamon bark in a model system study.They showed (I-prnene o,-terpineol
r:t cinnamon bark oil was susceptibleto oxidationwhereas B-pinene (E)-cinnamyl alcohol
--:rnamon leaf oil was resistant. The authors examined p-cymene cinnamylacetate
limonene caryophylleneoxide
r-i composition of cinnamon bark oil and reported that it
B-phellandrene cx-yrangene
:'-rrrtained: benzaldehyde
3-phenylpropanal
Cibromoethanel salicylaldehyde
cinnamylalcohol The followingyear, Nath et al. (1996) used GC/MS and
".rrfuraldehyde
renzaldehyde 2,4-dimethylacetophenonet GC to determine that an unusual chemotlpe of cinnamon
ccimene* cadinene* bark that is not found in commerce possessedthe following
l-Iormyl-5-metnylluran' (Z)-cinnamaldehyde composition:
cenzonitrilet phenol
J-terprnene (E)-cinnamaldehyde o-pinene(1.10%) ethyl benzoate(0.08o/o)
acetophenone cr-cedrener camphene(0.63%) methylchavicol(0.29%)
2-furfurylalcohol hydrocinnamicacid B-pinene(1.48%) cinnamaldehyde (0.68%)
longofolenet coumarin o-phellandrene(0.07"/") eugenol(0.13'l")
p-cymene(0.19%) meihyleugenol(0.06%)
' correct isomer not identified & limonene(3.15%) B-caryophyllene (1.90%)
- component identificationrequirescorroborationbefore being fully accepted
1,8-cineole (0.17%) eugenylacetate(O.21%)
linalool(3.42%) benzylbenzoate(86.69%)
In 1989, Variyar and Bandyopadhayayused retention
borneol(0.69%)
tir.nedata of authentic compounds on p packed GC column
to determine the composition of bark and twig oils of Using GC (retention indices) Bouzid et al. (1997) ana-
CinnamomumzeylanicumofKerala (India) origin. The corn- lyzed an oil of cinnamon bark. The compounds identified
poundscharacterizedin theseoils can be seenin TableVIII. were as follows:

178
 It is of interest to note that cinnamon fruit oil is dissimilar
Table lX. Comparative chemical composition (o/o)of
cinnamon bark oils removed from distillationwater to both cinnamon bark oil and cinnamon ieaf oil.
by centrifugationand by extractionwith diethyl ether
C. L. Hicks and C. Abdullah, PhotoxitJationof cinnannn oil. Food
J.
Sci.,52, 1041-1046(1987).
Distillationwater
Em uls ionoil oil obtainedby P. S. Variyar and Bandyopadhayay, On sonrc chemical a,sy.tects
of
obtained by diethyl ether Cinnanutmum zeqlanicum.PAFAI, (OcVDec), 35-38 ( 1989).
Compound centrifugation extraction B-Q. Cheng and X-|. Y:u, Cultiaation of Ceulon cinnanton and
o-phellandrene
+ limonene 0. 61 0.45 chentical cctntponbntsof its essential"oil. Zhotgcao_vao,l4(3),
linalool 2.24 2. 25 134-137(19e3).
camphor 3. 08 3. 10 A. Jayatilaka,S. K. Pooie, C. F. Poole and T. M. P. Chichila,
o,-terpineol 1. 33 I .JZ Sirnrtltaneousnicrosteam rJistillation/soloerLtextraction for the
(E)-cinnamaldehyde is_olationof serniuolatilefla.oor conrytound,s frtnn cinnanion ancl
81. 05 83.65
eugenol tl'Leirsepar ut i on b y seri eis coupl ed- colutm gas chr omatogr aphq .
4.33 3. 11 -
(E)-cinnamyl
acetate Anal. Chirn. Acta., 3O2, I47-162 (1995).
1. 50 0. 98
o-methoxy-cinnamaldehyde 0. 36 0.33 S. C. Nath, M. G. PathakandA. Baruah,Benzrllbenzoate,themtrjor
component of the leaf ancl stem bark oil of Cinnamorrutm
benzylbenzoate 0. 20 0 zeylarLiutmBltnne.l. Esscnt.Oil, Res.,8, 32i-328 (1996).
N. Bouzid, K. Toulgouate, G. Villarem and A. Gaset, Analq,se
benzaldehyde(0.54./.) (I{erprneol(0.07%) quantit atixe d.es;fractions d' huile essentielle pouoant co-aiister
a-pinene(3.47o/") (E)-cinnamaldehy de (46.52o/o) lors d'hy tlrodistillation deplants ororuttiqLte* ni"ista Itat. EppOS,
camphor(1.58o/.) eugenol(3.63'/") (April), 15-25(1997).
myrcene(0.07%) c-copaene(1.4O%) G. K. Jayaprakasha,L. JaganmohanRao and K. K. Sakariah,Chernical
B-pinene(1.02%) (E)-cinnamyl acetate(2.64e composition tf the uolatile oil frorn the fruits of Cinnamonurrt
")
6-3-carene(230%) B-caryophyllene (6.24%) zeylanicuntBhmte. FIav. Fragr. J., 12, 331-333 ( 1997).
p-cymene(4.18%) o-humulene(0.85%)
B-phellandrene+ limonene eugenylacetate(0.30%)
(e.1 6% ) Wormwood Oil
o-methoxycinnamaldehyde
linalool(2.98%) (0.7e%) In 1982, Chialva et al. used GCIMS to analyzea sample of
camphor(2.60%) benzylbenzoale(1.B2ok)
wormwood oil and the static headspaceof ground worm-
The authorsalsoexaminedtlie oil tliat could be removed wood thatr,vaskept in avial for one hour at 60"C. The results
irom the distillation water by centrifugation and the oil that of these analysescan be seenin Table X. Unfortunately,the
as extractedfrom the distillation water bv extractionwith headspaceanalysisonly accountedlor 107o.The authorsdid
"r
diethyl ether. Table IX shorvsthe c,omponentsthese oils not discusswhat happened to the other 607o.
',r-erereDorted to contairr. Ten years later, Ravid et al. (1992) determined that the
Alsoln 1997,Jayaprakashaet al. analyzedtwo oils of the fenchonefound in wormr.voodoil in approximately5.SVowas
ruit of C. zetllanicutnby GC and GC/MS. Although the oils exclusivelythe (+)-fenchone enantiomer.
.r'ereproduced fi'orn fruit harr,'estedin two different loca- In 1993, Tucker et al. analyzecla commercial sample of
:rons in India, Karnataka and Kerala, the oil compositions wormwood oil by GC and GC/MS. The oil rvas found to
.i ele similar as can be seen from the following analvtical possessthe folkrwing composition:
:esults: (Z)-2-methyl-3-methytene- B_thujone(33.1j%)
a-pin en e(0.1 -1.6% ) (E)-cinnamyl acetate hept-s-ene (0.240/") (Z)-epoxyocimene (0.85%)
B -pin en (0
e .1-0 "6 % ) (42.4-54.2o/") cx,-pinene
(0.69%) linalool
1.74o/"\
myrcene(0-02%) cr-humulene (2.8-3.1%) gjenchene(0.1S%) lavandulylacetate (1.81%)
a-phellandrene (0.1-0.7"r"
1 germacrene D (0.7-0.8%) B-pinene(0.19%) B-caryophyilene (1.44%)
p-phellandrene (0.4-1.6%) germacrene B (1.7-2.0%) sabinene (2.910/") cls-sabinyl
acetate(9275%)
(E)-B-ocimene (0.2-0.5%) y-cadinene(1.2-1.60/0) myrcene (1.32%) lavandulolrc.71%\
(Z)-cinnamaldehyde 6-cadinene(2.3-3.0%) o-phellandrene (0.35q.) cis-sabinol
e.7O%\
(0.2-0.3%) B-guaiene (0.4%) cx-terpinene(0.16%) germacrene D (1.72%)
borneol(0.3-0.4%) nerolidol-(0.2-0.4%) limonene(0.210/.) B-selinene(O.g7o/o)
u-terpineol (0.3%) caryophyllene oxide(0.9-1.1%) 1,8-cineole(0.62%) nerylisobutyrale(1.44o/")
i E)-cinnamaldehyde globulol(0.5-0.6%) y-terpinene(0.41%) nerol(0.37%)
(0.6-4.3%) germacrene D-4-ol(0.3%) p-cymene (0.28%) geranylpropionale (2.08%)
rE)-cinnamyl alcohol 10-epi-y-eudesmol (0.4-0.5%) terpinolene(0.05%) geraniol (0.14%)
(2.0-2.2%) a-muurolol(Ots%) (Z)-3-hexenol(0.39%) chamazutene (0.11%)
eugenol(0.2-O.3o/o) cubenol(0;5-0.8%) o-thujone(3.42o/o)
3-phenylpropyl acetate T-cadinol(2.7-3.4%)
(2.e-4.3%) o- c adinol
AIsoin 1993,Kalembaet al. comparedthe compositionof
. ( 1. 0- 1. 5% )
: ! cop ae ne(1 .8-3 .1%) benzylber\ioate (2.7-2.8%) oils obtained from Artemi,siaabsinthum (absinthe)groun in
i-caryophyllene (9.2-13.7o/") methylpalmitate(0-0.3%) Poland, using GC and GC/MS as their method of analvsis.
methyloleate(0-0.3%) Oils produced from plants harvested at the pre-flori'ering
' ::rrect isomer not identified
stage,in full flower and after flou,'eringn ere founclto possess

179
 Table X. Comparative chemical composition (%) Table Xl. Comparative chemical composition (%)
of the oil and static headspace of wormwood of oils ol Aftemisia absinthum produced from plants
harvested at three stages of growth
Compound oil Headspace
0,-prnene Pre- Full- Post-
0. 1 2. 6
Flowering Flowering Flowering
campnene 0. 1 0. 8 Gompound oil oil oil
B-pinene 0. 2 2. 6
myrcene 0. 2 2. 3 campnene 0.44 0.95 1
cI-prnene 1.83 3.23 3.60
p-cymene < 0. 1 < 0. 1
B-pinene 0.33 0.39 0.24
1,8-cineole < 0. 1 < 0. 1 sabinene+ myrcene 21.05 5.67 8.23
ltmonene < 0. 1 < 0. 1
y-terpinene < 0. 1 < 0. 1 5-3-carene I t t
1,8-cineole 2.26 I z-oo 11 .1 3
Iinalool 6. 0 10. 6 p-cymene 0.59 0.77 I
B-thujone 2. 7 2. 0
B-phellandrene 0.36 0.12 0 .1 8
(Z)-epoxy-u-ocimene 16.7 10. 3
(E)-epoxy-o-ocimene 0. 7 cI-thujone I 8.03 6 .1 9
B-thujone 11.82 16.91 4.96
campnor 2. 5 t.c
B-caryophyllene 1.18 2.74 4 .8 1
terpinen-4-ol 2. 0 6 .0 linalool 0.86 0.91 1 .2 1
nerol 1. 2
geraniol 3. 1 chrysanthenylacetate* 6.71 6.95 6.32
terpinen-4-ol 2.20 1.73 z- t3
chrysanthenylacetate* 4. 4 0 .6 sabinylacetate. 13.28 20.13 1 6 .6 9
eugenol o. 4 dihydrocarvylacetate
c-cuoeDene 0. 4 + c{,-terpineol 0.45 o.J I 1 3 .7 0
B-bourbonene 0. 7
p-caryophyllene
r r9r yr duvldtv 0.94 0.56 0.78
1.6 geranylacetate 1 I I
nerylor geranyl2-methylbutyrate 3.2 nerylpropionate 1.83 0.52
nerylor geranyl2-methy-butyrate 2.1 nerol I t 0.94
u-bisabolol 1.0
geranylpropionate 1.38
cnamazulene
cr-bisabolol 0.68 o.74 o.ro
- correctisomernot identified
- correctisomernot identified;t = trace (< 0.01%)

quantitative differences in their compositions as shown in Also in 1995, Nin et al. obtained oils from 49 selected
Table XI. In addition, the authors found that the oil was A. absinthum mother plants. The plants were of different
stronqlv toxic to RhizoTcefthadominca (lessergrain borer), geographical origin, but were grown in Tuscany.Eight com-
nrildh toxic to Tribolium confunrm (darkllng grain beetle) pounds (a-thujone, B-thujone, Iinalool, terpinen-4-ol, 1,8-
tt rd Sit ophilu s granariu s (grain weevil).Also,it wasrepellent cineole, o-pinene, geraniol and nerol) of these oils were
i0 S. granarius, identified and their quantitativeamountsin eachof theseoils
Tir o yearslater, Bourrel et al. (1995) examinedthe com- were recorded. These compounds were selected because
prositionof wormwood oil after they had screened it for its of their potential antibacterial activity and becauseof the
;ntin.ricrobialcharacteristics.Using GC/MS astheir method fact that Kaul et al. (1976,cited in Nin et al. of 1995)reported
',f analysis,the authors determined that the oil contained: that rvormwood oil had strong antimicrobial properties. Nin
et al. found that, although the u-pinene, l,S-cineole, nerol,
sabinene(0.3%) t hy m ol( 1. 1% )
p-cymene(0.4%) carvacrol(2.6"/.)
geranioland u-thujone contentsof their oils were either low
terpinolene (0.5%) perillylalcohol(0.6%) (<3.07o) or not present, the other compounds varied as
linalool(4.6%) methyleugenol(1.7%) fbllows:
B-thujone(5.4%) ar-curcumene (5.2%)
p-menth-2,5-di en-7-ol (2.9ok) myristicin (1.0%) B-thujone(0-49.68%) terpinen-4-ol(0-11.64%)
linalool(0-6.63%)
camphor(0.4%) y-elemene(2.0%)
lavandulol (1.3%) spathulenol (4.6%) It is a shame that these authors did not monitor the
terpinen-4-ol (2.2%) caryophylleeeoxide (3.9%) cis-sabinylacetate,(Z)-epoxyocimeneand cis-chrysanthenyl
perillaldehyde (1.2%) 10-epi-y-eudesmol (1.5olo)
acetate contents. as it would have made their work more
nerol(2.9"k) palmitic?cid(3.7%)
(E)-anethole (0.9%) complete.
'i l This sameyear, Mucciarelli et al. (1995) performed GC/
This was not a particularly useful analysisof wormwood oil MS analysis on oils obtained from a number of Aftetnisia
because although the authors identified 23 components, speciesgrowing in northwest Italy. In this study, they deter-
these comprised only 50.97oof the total oil. mined that an oil of A. absinthum contained:

I80
 Tabfe Xff. Partial comparative chemical composition (%) of the oils of seven clones ol Artemisia absinthum

Compound 1 2 3 4 5 6 7
(X-prnene i 0 .3 t 1 t t t
campnene t 0 .1 0.1 t t I I

B-pinene 8 .7 4 .6 1.3 2.0 0.8 0.3 0. 8

myrcene 3.4 20.7 8.9 6.3 0.2 a4 9. 5
limonene 0 .7 I t I t 0.1
B-phellandrene t 0 .2 0.1 0.1 t 0.4 0. 8
T-terpinene 0 .1 0 .1 0.1 0.1 I t 0. 1
p-cymene 0 .1 0 .5 0.5 0.3 0.2 0. 7
o-thujone o4 0 .7 0.2 0.3 0.1 0. 1
Bthujone 39.2 58.2 29.8 34.1 0.1 0. 1
campnor t 0 .1 t t o.u t 0. 2
linalool 0 .3 1 .2 0.9 0.3 0.3 0.3 0. 5
chrysanthenylacetate* 0 .1 0 .6 0.3 0.3 0.1 0.3 0. 1
sabinylacetate- 0 .3 27.2 30.5 27.0 27.2 38.0 70.7
Total 5 3 .3 84.5 72.7 70.8 29.4 43.1 83.7
* correctisomer
not identified;t = trace (< 0.1%)

o-pinene(0.3%) sabinylacetate"(1.6%) thujone is generallyconsideredto be the toxic constituent.

a,thujene(0.3olo) myrtenal(0"1%) However, the toxicity of absinthe might also be associated
a{enchene(t) cuminaldehyde (0.2%)
camphene(t) artemisiaketone(t)
with the sabinyl acetate content of the herb, especially
B-pinene(0.7%) camphenilone (t) becausethis compound dominatesthe compositionof some
sabinene(1.6%) uthujone (67.5%) of'the clones studied.
myrcene(t) B-thujone(18.2'/.) More recently, Pino et al. (1997) analyzed an oil of A.
u-phellandrene (t) camphor(0.4%) absinthum produced from plants grown in Cuba. Using a
c-terpinene(0.3%) isopinocamphone (t)
limon en e(0 .1% ) pinocarvone(0.2%) combination of GC (for retention indices and quantitative
lterpinene (0.6%) verbenone(t) data) and GC/MS (for component identification) the oil,
p-cymene(1.0%) carvone(t) which is an example of yet another wormwood chemotype,
terpinolene (0.1%) damascenone.(t) was found to contain the following components:
trans-sabinene hydrate 2,3-dihydro-1,8-cineole (t)
(0.2o/4 1,8-cineole(2.0%) tricyclene(0.10%) terpinen-4-ol (8.15%)
yomogialcohol(t) (Z)-epoxyocimene (t) cr-thujene(0.58%) s-terpineol(4.80%)
cis-thuj-2-en-4-ol (0.4ok) linalooloxide.(0.1%) o-pinene(1.24o/") verbenone(2.47%)
artemisiaalcohol(t) ascaridole(t) camphene(2.02o/") cis-p-menth-2-en-7-ol (0.50%)
linalool(t) o-copaene(0.2%) sabinene(4.61%) cuminaldehyde (0.93%)
terpinen-4-ol (1.3%) yselinene(0.6%) B-pinene(0.69%) bornyl acetate (23.02%)
pinocarveol-(t) (0.5%) myrcene(1.08%) perillylacelate(0.20%)
B-caryophyllene
frans-verbenol(t) (E)-nerolidol (t) uterpinene(1.55%) p-mentha-1,4-dien-7-ol (0.24%)
c{-terpineol(t) epi-cubenol (t) p-cymene(1.55%) crterpinylacetate(0.09%)
borneol(t) spathulenol (0.1%) 1 , 8 - c i n e o l(e5 . 1 0 %) p-menth-1 (7)-en-9-ol
(0.14%)
nojikualcohol..(t) o-bisabolol(t) (Z)-p-ocimene (0.06%) eugenol(O.07%)
myrtenol(0.1ol.) frans-cr-bergamotol (t) (E)-B-ocimene (0.20o/o) cis-carvylacetate(0.10%)
irans-carveol(i) o-cadinol(t) y-terpinene(2.O8%) B-caryophyllene (0.66%)
cis-chrysanihenylacetate (t) caryophylleneoxide (0.4%) cls-sabinenehydrate(0.29%) (Z)-B-f arnesene(0.11'/.)
tranechrysanthenylacetate (t) bisabololoxide-(t) eucarvone(0.06%) cr-humulene (0.08%)
bomyl acetate (t) carvacrol 0-p-dimethylstyrene (0.06%) (E)-B{arnesene(O.26%)
terpinolene(0.75o/o) viridiflorene(0.41o/o)
linalool(2.00%) caryophyllene oxide(0.67%)
- :oreci isomer not identified
- also known as camphene-6-ol B-thujone(0.29"/.) o-cadinol(O.17%)
: = trace (< 0.1%) t* safranal(0.59%) chamazulene(0.26%)

,\ r ear iater, Lamarti et al. (1996)e-xaminedthe composi-
:,,rr of oils produced from sevenclorqe,s
of A. absinthum thal
-',tre obtained via micropropagatioir. The results of the
,i":.Jvsesof these oils can be found in Table XII. The authors
-r:icd that when the toxicity of absinthe is discussed,B-
Chinlva, G. Gabri, P. A. P. Liddle and F. Ulian, Quantitatioe
euafuation of aromatic her:bsb y d irect headspace1Ge )2 analysi,s,
Applications of the m.ethodand comparison uiththe traditional
analysis of essential oils. ln: Aromatic plants: basic and applied
aspects.trdits., N. Margaris,A. Koedam and D. Vokou, pp. fB3-
195, Martinus Nijhoff Publishers,The Hague (1982).
U. Ravid. E. Putievsky, I. Katzir and R.Ikan,Chiral GC analysis of
enanti,omericallyiurefenchone in essentialoils' Flav' Fragr' J', 7,
169-172(1992).
O. Tucker. M. T. Maciarello and G. Sturtz, The essential oils of
Artemi,sia "PlowisCastle" and its putati,oeparents A. absinthum
and A. arborescens.J.Essent.Oil Res.,5'239-242 (1993)'
D. Kalemba, T. Gora, A. Kurowska, T. Majda and Z. Mielnizuk,
Analqsi.sof essential oils in aspectsof their influence to i'nsects'
ZeszvWN"auk.Politechnik. Lodz', No. 589,5-14 (1993)'
C. go,r.."l, C. Vilarem, G. Michel andA. Gaset,EtuiLed'espropridtls
bacteri.ostatiqueset fongistatt'ques en rnilieu solide d'e24 Lruiles
essentiellesprdambiemint analysties' Rivista Ital' EPPOS, No'
16. 3-12 (1995).
S. Nin, P. Artaioli and M. Bosetto, Quantitatit:e determi.nation oJ
components of ielected Artemisia absinthum
-sorne essential oil
plants.!. Essent.Oil Res.,7,271-277(1995)'
M. Mucciarelli, R. Caramiello, M. MaffeiandF. Chialva,Essential
oils from som'e Artemisia speciesgrowing sponlaneously in
Northuest ltalA. Flav. Fragr. J., f 0. 25-32 (1995).
A. Lamarti,I. Sadki,A. Badoc, G. Def{ieuxandJ-P. Carde, Obtention
par culture in aitro de clonesd' absinthe, Artemisia absi'nthumL'
'derruis
de tLruyone. Bull. Soc. Pharm' Bordeaux, L35, 25-43
( 1996).
A. Pino, A. Rosado and V. Fuente s, Chemical composition of the
"J.
essential oil of Artemisi,aabsinthum L. from Cuba J. Essent Oil
Res.,9, 87-89(1997).
 Progress in Essential Oils
Reprinted
fromPerfumer
& Flavorist, 'lgg8,Vol.23,No.2,p.47
March/April

Sage Oil The followingyear, Bernath et al. (1991) examined the

In 1983, Cordoba Rodriguez compared the chemical com- oil accumulation and variation as affected by different envi-
position of Spanish sage oil with that of sage oil ex. ronments. They found that two strains o{ S. fficinalis
Saloiafficinalis. She found that th e S.fficinali.s oil studied differed in the amount of oils accumlated,but in each case
possessedthe following composition: the oils contained the followine constituents:
(Z)-salvene (0.4%) terpinolene (0.2%) o(-prnene B-selinene
(E)-salvene (0.1%) lrans-sabinenehydrate(0.1%) B-pinene campnor
tricyclene(0.2%) cr-thujone(26.5o/") 1,8-cineole ledol
o,-thujene(0.3%) B-thujone (4.3%) thujone.- bornylacetate
a-pinene(4.8%) camphor(16.8%) borneol
camphene(6.2%) linalool(0.5%)
-- although not given, the isomer was o-thujone
sabinene(0.2%) linalylacetate(0.5%)
B-pinene(2.3%) borneol(2.1%) The authorsdid not presentany intelpretable data on the
myrcen e(1.1 % ) bornylacetate(1.4%) quantitative amounts of these compounds; however, they
a-phellandrene (0.1%) terpinen-4-ol (0.3%)
p-cymene(2.0%) (0.5%)
o,-terpineol
did note that thujone, B-selineneand ledol were the domi-
limo ne ne(3.1 % ) acetate(0.2%)
cr,-terpinyl nant components.
p-phellandrene (0.9%) sabinylacetate.(0.3%) A year later, Jean et al. (1992) compared the chemical
1,8-cine ole(11 .1'/.) u-humulene(5.0%) composition of an oil of sageproduced by hydrodiffusion
(Z)-B-ocimene (0.2%) B-caryophyllene (3.3%) with a microwave extract of sageplants. The results of this
7-terpinene (0.3%)
study are summarizedin Table I.
In 1993,Holla and Vaverkovacompared the composition
Sevenyears later, Kreis et al. (f990) used enantiomeric oI S. fficinttlls grown in three different Slovakian localities.
separationon a chiral capillaryGC column to determine that A summaryof their anall,ticalresultscan be seenin Table IL
the enantiomericratiosof cr-pinene,F-pineneand limonene This sameyear,Ld"ngeret al. (1993)reported the prelimi-
in sageoil were: nary results of a study in which they cut single fresh sage
(S)-(-)-a-pinene
(s5%): (R)-(+)-o,-pinene leavesin half. From one leaf half they immediately isolated
(65%)
(S)-(-)-B-pinen
e (87'/.): (R)-(+)-p-pinene
( 13olo) the oil and from the other halfthey extracted the oil after the
(S)-(-)-l
imonene (30%): (R)-(+)-limonene (70%) leaf half had dried for two months at room temoerature.The
oils of 24 leaveswere analyzedand comparedln pairs (as S.

Table l. Comparativechemical composition (%) fficinalis has opposingleaves).The authors found some oil
of sage oil and a microwave extract of sage

Table ll. Comparativechemicalcomposition (%) of

Compound Sage oila Sage extractb sage oil produced from plants harvested in three
a-pinene 2. 5 1. 5 different regions of Slovakia
campnene 2. 4 1"6
p-pinene 2. 4 1. 3 Compound Hurbanovo Nova Labovna Plavnica
myrcene '1.1 0.9
o-pinene 4.44 4.63 4.58
limonene+ 1,8-cineole 6. 8 10. 9 camphene 5.51 5.21 4.32
cr-thujone 39.4 48.4 p-pinene 2.48 2.12 1 .8 2
3-thujone 8. 9 limonene 1.12 1.10 2 .5 2
campnor 12.1 14.2
1,8-cineole 9.91 7.92 7.86
borneol 0. 6 1. 4 p-cymene 0.69 0.54 0.64
hnrn\/l aaa+2fa 0. 7 0. 7 crihujone 36.70 35.00 31.50
p-caryophyllene 2. 4 0. 5 camphor 15.70 14.20 13.80
cr-humulene 6. 0 1. 2 bornylacetate 6.50 5.12 4.22
5 .0 3. 0 borneol 13.30 13.60 11 .3 0
: orlproducedby hydrodiffusion terpinen-4-ol 0.52 0.49 0.54
: averageof nine individualextracts B-caryophyllene 6.49 4.56 4.22
composition differences between individual leaf pairs; how- linalool(0.28%) 8-cadinene(0.23'/.)
ever, these differenceswere more pronounced when com- linalylacetate(0.10%) geraniol(0.15%)
bornylacetate(0.37%) caryophylleneoxide (1.44%)
paring the Ieavesat the top node to leavesat the basenode.
terpinen-4-ol(0.69%) s-muurolol(2.25o/o)
For example, the u-thujone and camphor contents varied lene (2.99ok) viridiflorol(10.92%)
B-caryophyl
Irom 56.67oto 3l .37oand 5 .87oto 29 .1,7o
, respectively.The 6-terpineol(0.21%) spathulenol(0.25%)
authors did not find anv clear compositional correlations s-humulene(0.27%) s-cadinol(0.21%)
between fresh and driedleaf oils. crterpineol(3.10%) manool(3.57%)
borneol(6.69%)
Sage oil was screened against 25 strains of bacteria
by Piccaglia et al. (1993) to determine its antimicrobial This same year, Reverchon et al. (1995) compared the
characteristics.The oil used contained the following major composition of a supercritical fluid CO, extract (SFE) of
components: dried sage leaves with that of an oil produced by steam
(5-13%)
1,8-cineole distillation from the same lot of sageIeaves.The results of
B-thujone(4-10o/o)
cr{hujone(36-46%) camphor(16-21%) the GC/MS analysisof the SFE and the oil can be seen in
Table IV.
It was found to possessmoderate antimicrobial activity
Reverchon et al. also reoorted that the cuticular wares
and antioxidant activity. The antioxidant activitywas thought
comprisedthe following hydrocarbons:
to be directly related to the major componentslisted above.
Also in 1993, Bouverat-Bernier and Marquis examined eicosane(0.24%) triacontane(0.75'/.)
the major component compositionof the oil of sevenclones heneicosane (0.58%) methylnonacosane.(0.68%)
docosane(0.44"/.) hentriacontane(20.95%)
o{ S. officinalis harvested at three different growth stages pentacosane(0.50%) dotriacontane(3.25%)
over the 1990-1991 season.The comoosition of these oils hexacosane(O.49%) methyltriacontane- (2.84%)
can be seenin Table IIL As can be seenfrom the results (in heptacosane (1.13%) tritriacontane(58.21%)
which data from the early and late vegetative stageswere octacosane(0.53%) methyldotriacontane- (2.09%)
6-methyloctacosane(5.78%) methyltriacontane. (1.57%)
combined and comparedwith data from the plant harvested
in full flower), the components varied quite dramatically. In * correct isomer
not identified
particular, the camphor and thujone contents were quite
The authors concluded that the composition of sage
varied. It also was interesting to note that the l,8-cineole
extract was largely influenced by extraction time and solvent
content of the oil obtained from the plants harvested in full
density.
flower was always drastically greater than the content of the
As part of an antimicrobial screeningprogram, Bourrel et
oil obtained from vegetative plants.
al. (f995) examinedthe chemical compositionof sageoil by
In 1995, SanchezGomez et al. (1995) used both GC and
GCiMS. The oil was found to contain:
GC/MS to determine that an oil of S. fficinalis obtained
fiom plants that they used in a hybridization study contained: cr-pinene(0.2%) B-thujone(6.4%)
camphene(0.5%) camphor(6.1%)
0-thujene(0.06%) (Z)-B-ocimene (0.78'/.) s a b i n e n e( 0 . 1 %) pinocamphone(0.6%)
o,-pinene(2.98o/o) yterpinene (0.30%) B-pinene(0.9%) borneol(1.2%)
camphene(2.10o/o) (E)-B-ocimene (0.17%) myrcene(0.4%) (0.6%)
terpinen-4-ol
B-pinene(8.93%) p-cymene(0.49%) p-cymene(0.3%) (0.1%)
o-terpineol
sabinene(O.07%) terpinolene(0.17o/o) 1,9-cineole(2.2"/") myrtenol(0.3olo)
myrcene(0.50%) o-thujone(22.82%) yterpinene (0.2%) bornylacetate(0.1%)
cr-terpinene (O.44'/") Bthujone (4.32%) Bterpineol.(0.3%) thymol(0.2%)
1,8-cineole (15.71%) camphor(4.99%) cr-thujone(63.3%) B-caryophyllene(0.7%)

Tabfe ffl. Major component composition (%) of oils of various clones of S. ofticinalis

Compound 1V lF 2V 2F 3V 3F 4V 4F 5V 5F 6V 6F 7V 7F
tx-prnene 3.0 4.0 2.0-3.0 6.0 3.0 4.0 0-3.0 4.0 3.0 7.0 2.0-3.0 8.0 2.3-3.0 6.0
p-pinene 2.0-3.0 7.0 1.0-6.0 1 1 .0 2 .0 5.0 2.0 6.0 4.0-6.0 10.0 4.0-6.0 13.0 4.0- 5. 0 10. 0
1,8-cineole 11.0-12.0 20.0 8.0-9.0 25.0 12.0-14.027.0 11.0-16.029.0 7.0-12.022.0 13.0-14.0
28.0 14.0-16.032.0
d-thujone 28.0-40.037.0 13.0-1
5.0 13.0 30.0-35.030.0 34.0-36.031.0 29.0-35.0 .0 6.0 21.0-31.014.0
15.0 16.0-31
p{hujone 13.0-15.015.0 9.0-1 1.0
1.0i* 9.0 7.0-9.0 8.0 9.0-1 9.0 3.0-13.03.0 8.0-14.04.0 8.9-1 9.0 11.0
camphor 7"0-10.0 4.0 32.0-33.015"0 13.0-15.0 6.0 13.0 10.0 .0 7.0 10.0-16.0
6.0-21 2.0 11.0-1 2. 0 3. 0
borneol 1. 0 1 .0 3.0-4i 4 .0 1 .0 1.0 1.0 1.0 1.0-6.0 16.0 1.0-2.0 15.0 1.0-2.0 4.0
3.0-4.0 3.0 3.0-4.0 5.0 4.0-7.0 7.0 4.0-5.0
B-caryophyllene 4.0 1.0-2.0 1.0 4.0-6.0 5.0 3.0 6.0
1-7 = clones ol S. officinalis
V = vegetativestage
F = floweringstage
 ,:r-humulene(0.2%) pogostol--(8.3%) (0.18%)
T-cadinene caryophylleneoxide (0.34%)
rr-guaiene
(0.1%) caryophylleneoxide (0.5%) 6-caQinene
(4.61%) globulol(2J2%)
rguaiene (t) hum ulene
ox ide lI ( 1. 2k )
,-cadinene(0.2%)
Using CC and retention times of knou,rr compounds.
' :.nect isomer not identified
*
Venskuton is.i 1gg5) reporled t hata Jab-distil
led oil p roduced
:oubtful constituent,probably a misidentification
: = : ' a c e (< 0 .1 %) trom sagepl antsgrow n i n Li thuani acontaj ned:

\lso in 1995, Pace and piccaglia used a combination of o-thujene(0.15%) cr-thujone (19.58%)
{:C and GC/M Sto analyzethe oil produced from S.officinalis ct-prnene
(6.05%) B-thujone(13.43%)
.. ar.artgtrstlfuliaTen.,a wild camphene(5.14./") c a m p h o r( 1 1 . 6 3 %)
Italian endemic sagevarietv sabinene(0.09%)
Tre corlpounds identified in the oil were: borneol(2.04o/o)
B-pinene(2.11o/o) methylchavicol(0.20%)
Zi-salvene(0.57./") othujone (39.32./") myrcene(1.00%) bornylacetate(1.34o/o)
E,-safvene(0.07o/") s-terpinene(0.24%) e (6.57ok)
B-thujone(3.07%) B-caryophyllen
r-:hujene(0.25o/") camphor(2.12%) p-cymene(0.60%) s-humulene(5.24%)
-r-pnene(1.21%) borneol(0.67%) limonene(1.670/") viridiflorol (4.58o/o)
=nphene (0.85%) terptnen-4-ol(0.39%) 1,B-cineole
(10.06%)
sairnene(0.31%) bornylacetate(0.28%)
:-r nene(7.22%) s-cubebene(0.16%) A year later, Ravid et al. (1gg6) examined the enantio_
- r.cene(0.75%) o-ylangene(0.22o/o) meric distribution of borneol in sageoil. Using chiral GC
,r-:efprnene
(0.31%) o(-copaene(0.34%) analysis on a permethylated B-cyclodextrin column, the
:-.yinene (0.51%) cr-gurjunene (0.10%)
Tonene(0.670/")
authors determined that borneol, which was founcl at 0.g_
B-caryophyllene (9.05%)
' 3-cineole(7.73%) aromadendrene
3.97oin the oil, had the following distribution:
(1.67%)
Z -3-ocimene (1]s%) s-humulene(12.42o/") (lR)-(+)-borneot
(11-16%)
: (tS)-(*)_borneot
(84_89%,1
! -p-ocimene (0.3j%) allo-aromadendrene (0.13%)
'-:erDinene(0.620/o) y-muurolene Also in 1996, Chane Ming et al. repofted that an oil of S.
(0.51%)
::': nolene(0.06%) viridiflorene
(0.99%)
fficinali,s of Reunion origin was sublectedto analysisusing

Table lV. Comparatlve chemical composition (/o) ot a

supercritical fluid co, (sF) extract of sage with that 6f sage oil

Compound SF Extract Oil Compound SF Extract Oil Compound SF Extract oi l

:'tr,'clene tt &-terpineol 1.61 1.84 T-curcumene t
."-:- 0.1 1 0. 11 cls-carveol 0.25
-jene 0.17 ar-curcumene 0.07
2.37 3.76 (Z)-anethole tt
:a-chene B-selinene 0.28
1.0 2 1. 37 piperitone 0.18 0.27 valencene t
2.44 2.69 linalylacetate 0.17 I viridiflorene 0-29 r
2.2 9 1. 87 (E)-anethole 1 cI-selinene o.20 0.1 5
0.1 6 t bornylacetate 0.38 0.73 g-muurotene 0.20 0.24
0 .11 0. 28 thymol t 0 . 11 B-bisabolene 1.04 1.0 2
:-t,.nene 1.8 2 1. 15 menthylacetate 0.43
' 3-c neole 0.64 1-cadinene 1.46 1.3 9
54.36 59.05 carvacrol 0.93 t.z z 6-cadinene 0.26 0.1 9
0.2 5 0. 41 isomenthylacetate t cr-calacorene 0.11 0.1 1
0.33 t carvytacetate" t cls-calamenene 0.13 0.21
0.65 0.34 o-terpinylacetate 0.44 0.34
,r-i="trnytacetate B-calacorene 0.16 0.1 2
o.20 a-cubebene 0.32 o.14 ledol 0.16 0.17
1 .3B 1. 20 o(-copaene I spathulenol
1-:--one 0.50 0.96
1.4 2 0.99 longifolene o.07 globulol 0.14 0.2 0
E-3nor 5.22 c[-gurJunene t cl+cr-santalol 0.26 0.28
-r3-:1rOne o.29 0.45 B-caryophyllene 7.06 4.22 Kaurene 0.23
s:ccmeol 0 .17 0. 13 0.12
_f-=n l
B-gurjunene manool 1.79 0.40
0 .81 0.78 aromadendrene 0.85 0.48 sclareol 0.12 t
-B:renthol 0.49 0.46 d:guaiene
*g-:lol o.07
0.73 1. 19 o-humulene 1.27 o.rn
"rP--:-en-4-ol -
0.66 0. 96 allo-aromadendrene0 . 1 1
:* 1'ren-B - o l 0.1 1 I \,, Y-muurolene 0"16

:r-=ci isomernot identified

= :-=:e (< 0.01%)
GC ({br retention indices and quantitativedata)and GC/MS
(for component identityverification). The compoundsiden- Table V. Comparativecomposition (%) of
extracts and oils ol Salvia officinalis
tified in the oil rvere:
7-methyl-3,4-octadiene B{hujone(12.97%) Singleleaf Leaf Hydrodistilled
Hydrodistilled
(0 .1s% ) camphor(20.18%) Compound extractsl extracts2 oill oils2
tricyclene (0.13%) pinocamphone (0.760/")
cr-thujene(2.52%) borneol(1.87%) d-prnene 1.9-19.2 0.7-13.6 5.0 0 - 8 .0
cr-pin en(2.7
e 1% ) terpinen-4-ol (0.56%) campnene 0 . 7 - 1" 0 1 . 6 -1 2 . 3 1.7 0 - 8 "6
sab ine ne(1.6 3% ) aierpineol(0.24%) B-pinene 0 . 1 - 1. B 0 - 1. B O.4 0-1.2
B -p ine ne(A 7 2% ) myrtenol(0.14%) 1,8-cineole 10.9-43.1 2.8-22.8 18.7 1.8-21.7
(1.1B% )
B -p he llan dre ne bornylacetate(2.27%) cr{hujone 15.7-59.3 7 .5-41.9 46.3 1 3 .1 - 4 8 .5
limonene(4.04%) B-caryophyllen e (1.32%) 4.9-25.8 2.5-18.0 18.6 3 .9 - 19 .1
(o 2to/^\
B-thujone
'/-torninon6 cr-humulene (3.61%) camphor 1.4-30.4 14-4-47.4 7.3 7.3-50.2
caryophyllene oxide(0.17%) borneol 0 . 4 - 10 . 8 2 . 1 - 2 2 . 7 1. 5 1 .5 - 2 3 .9
ci-thujone(33.25%) (3.77%)
viridiflorol
linalo ol(t) manool(2.71"h) bornylacetate 0.1-8.0 0.4-9.8 0.3 0 .3 - 5 .7
B - c a r y o p h y l l e n0e. 1 - 4 . 7 0.6-15.9 u.z 0.2-9.7
t = tra ce (< 0 .0 1 ',;)
I singlecommercialsourceo'fsage leaves
2 25 differentcommercialsourcesof saoe leaves
-\iso in 1996, Perry et al. analyzeda series of oils of S.
nfricinalisproclucedfrom plants grown in Neu'Zealandin an
e\perinuntal galden. either {iom seed or from cuttings
accprireclfronr different sources.The plants were divided This same year, Ldnger et al. (1996) used methylene
into hr-o qroups; those rvhich flowered and those which chloride to extract each of 50 dried sage leaves obtained
rareh'flos-erecl.The flowering tlpes r'vereproducecl {i'om frorn a single commercial source.They compared the main
seecltnine selections),rvhile the ia.ely flo.teiing tlpes lr,ere comoonent comnosition of these extracts with that of
gro\\l frtrm cuttings or rooted plants (four selections) hvdrodlstllled oil produced from 10 g of clried leavesfrom
obtainecllocrrllvin Nerv Zealand.The compoundsidentified the same source.Furthermore, they compared the oils and
in oils fronr all S. fficina1l.s plants,u"r" u, follorvs: extractsof dried sageleavesfrom 25 different commercial
sources.Their resuits can be seen in Table \r. The authors
(Z)-salvene (x-ylangene
tricyclene R-nr rhahana believedthat the rvidevariationin ouzrntitativeamountsof oil
0-thuJene B-bourbonene constituents rvas a direc't t.rult of age differences in the
cI'pinene B-caryophyllene leavesertracted or distilled.
aromadendrene Also in 1996, Carta et al. used both GC and CC/MS to
^^ L i ^^^^ o- hum ulene determine that an oil of S. fficinalis of commercial origin
B-pinene cr-amorpnene
myrcene germacrene D contained the follor,vingconstituents:
1,8-cine ole bicyclogermacrene (3.69%)
cr-pinene camphor(26.85%)
ltmon en e B-selinene o-thujene(0.11%) l i n a l o o(l1 . 9 5 %)
(Z)-B-ocimene cr-muurolene camphene(5.80%) bornylacetate(1.53%)
T{erpinene (E,E)-o{arnesene ( 1 . 5 8 %) (4.59%)
B-pinene B-caryophyllene
p-cymene 6-cadinene myrcene(0.69%) terpinen-4-ol (0.39%)
'1-octen-3-ol frans-calamenene p-cymene(0.90%) pinocarveol* (6.65%)
0-thujone o-calacorene limonene(2.64%) cr-terpinyl acetate(0.47%)
linalool g-cadinene 1,8-cineole(11.82o/o) (0.11%)
cr{erpineol
R-nrlrnnrona
Bthujone y-terpinene (0.16%) borneol(2.95'/")
camphor palustrol a-thujone(23.OO%) caryophyllene oxide(0.34%)
prnocampnone DP4U rUrVr rUl
B{hujone(3.80%)
^^^+h..1^h^l

borneol caryophylleneoxide
bornylacetate viridiflorol
hum uleneox ide*
cr-gurJunene manool The {bllowing year,Piccagliaet al. (1997)detennined the
cr-cubebene composition clf sageoi1produced from plants harvestedat
* di{Ierent stagesof maturity. A summar-vof these analytical
correct isomer not identitied
results can be found in Table VI.
Unfortunatelv, the authors dicl not present any quantita- This sameyear,Pino et til. (1997)used GC and GC/MS to
tive data, although they did note tlrrft tlie total thujone a:aalyzean oil of S. officinalis produced from plants grorvn in
content r,vasI0-3I7a in oils of flor.verjngplants and 6-8% in Cuba. The compositionof the oil was found to be as fbllows:
oils of rarely flor,veringplants. Furthermore, the authors
o - p i n e n e( 0 . 8 1 %) limonene(1.69%)
noted that there lr.ere signi{icant',variationsin the tr'vo camphene(2.48%)
.1 (1.81%)
,B-cineole
thujones, B-caryophyllene and viridi{lorol betr'r'eenthe B-pinene(0.96%) (Z)-b-ocimene (0.19%)
oils of plants of differing flowering capacities.They used cx,-phellandrene (1.16%) y-terpinene(0.29%)
principal component analysisto reach this conclusion. cr-terpinene (0.12%) p-cymene(0.35%)

I86
 M. de los Angelos Cordoba Rodriguez, Contribucion al estutJiod,el
Table Vl- Percentagecomposition (%) of sage oil aceite esencial d e Saluia EsTtanola (,Sahtialaxanduloefolia V ahl).
produced from plants harvested at different times Ph.D. thesis,Univ. Complutense,Madrid (1983).
B. M. Lawrence, A reaiera of the u;odd, procluction of essential oils
April 23 May 26-JuneI October 26 (1984).Perfurn.Flavor.,10(5), f-16 (1985).
vegetative llowering vegetative P. Kreis, U. Hener and A. Mosandl,Chirnle Inhaltstofferitheri,scher
Compound period period period
Ole. I I I Sterodffi renzierun g L)on ct-Pinen, & Pinei u nd L i monen
(Z)-salvene 0 . 14 0.34-0.36 0.34-0.41 in ritherischen Olen, Drogcn und Feftigar:ncimitteln. Deut.
(E)-salvene 0 . 02 0. 09- 0. 11 0. 08- 0 . 1 1 A p o r h .Z r g . 1 3 0 9 5 8 - 9 E 8 ,t 9 9 0 ) .
0 . 10 0.27 0. 16- 0.6 3
J. Bernath, B. Danos and E. Hethelly, Variation in essentialoil
cr-pinene 0 . 56 2. 41- 3. 21 2.07-2.92 spectntm of Solaia ,speciesfficted bq enxironment. Herlta.
camphene 0.63 1. 41- 1
. 72 2. 15- 2 . 7 9 Hung., 3o (1/2),35-46 (1991).
sabinene 0.22 0.26-0.32 0.22-0.30 F. L Jean,G. J. Collin and D. Lord, Essentialoils anrJrnicrouru:e
B-pinene 2.82 10.62-12.87 2.06-2.38 extractsof ailttuated plant,s.Perfum. Flavor.,t7(3),35-41(1992).
myrcene 0.78 0.72-0.83 0. 98- 1. 14 M. Holla and S. Vaverkova, Tlrc content and comltositiortof aolatile
cx-terpinene 0. 11 0.23-0.24 o. 12- 0 . 1 7 oil from Solaia fficinalis L. in clependenceon the locality oJ'
p-cymene 0. 22 o.23-0.27 0.42-0.48 g'rouing. Biologia Bratislava,48, 619-621 (f993).
ilmonene 0.59 0. 61- 0. 91 0. 96- 1. 1 8 R. L:inger,Ch. Mechtler, H. O. TanzlerandJ.Jurenitsch,Dffirence
1,8-cineole 4.93 16.59-17.74 9. 14- 9.15 oJ the conpo,sition of the essential oil within an irrcliairhnLmof
(Z)-B-ocimene Saloia cfficinalis. Planta Med., 59, (Suppl. Issue),A635-A636
0.84 0. 95- 1. 05 0. 12- 0.13
(E)-B-ocimene 0. 15 0.22-0.24 o. 02
(ree3).
yterpinene 0.44 0.43-0.45 0. 31- 0. 3 8 R. Piccaglia,M. Marotti, E. Giovanelli,S.G. DeansandE.Eaglesham,
terpinolene 0. 11 o.16-0.27 0, 17- 0 . 2 3 Antib acterial rLnd anti oxitlartt p rop ertie,s of M edit enan ean
arctmnticplanfs. Indust. Crops Products,(2), 47-50 (1993).
ilnalool 0 . 18 0.25-0.35 0. 16- 0 . 2 1
o-thujone 29.66 24.55-25.86 44.71-48.93 J-P.Bouverat-Bernier and N. Marquis, Premiersresultatsdeselection
5 . 81 5. 18- 5. 32 8.86-9.27 de la saugenfficinale. Rivista ital. EPPOS (Numero Speciale),
B-thujone
campnor 13 . 40 1. 75- 3. 62 8. 97- 10 . 0 9 58r-592 (1993).
P. SanchezGornez, M. C. SorianoCano, J. A. SotomayorSdnchez
borneol 1. 31 2.98-4.04 1. 09- 1. 14
and M. C. GarciS-Vallejo, Esserttial oils of a neu hybrid Salaia
terpinen-4-ol 0 . 33 0.41 0.37-0.39
bornylacetate 0 . 25 0. 16- 0. 64 0.20-0.27 fficinalis x S,laoonclulifoliassp.r,ellerea.J. Essent.Oil Res.,7,
3 1 7 - 3 8 r( 1 9 9 5 ) .
B-caryophyllene 8. 96 6. 77- 7. 19 1. 66- 1 . 8 2
E. Reverchon,R. Taddeo and G. Della Potta,Extraction of sageoil
aromaoenorene 0.33 0. 15- 0. 31 0.07-0.08 by supercritical COr: Influence of some process poia,,tr:turs.
c,-humulene 13-97 5.95-6.54 2.65-2.78
J. SupercriticalFluids, 8, 302-309(1995).
allo-aromadendrene 0.33 0. 11- 0.13 0.04
Bourrel, G. Vilarem, G. Michel andA. Gaset,Efiule clespropridtis
caryophylleneoxide 0. 69 o.28-0.32 0.19-0.27
bacterio,statique,s
et fongistatiques en rnilieu solide de 21 Ltuiles
viridiflorol 3.04-4.63 es,sentiellesprdontblunent anolysdes.Rlvista Ital. EPPOS, No.
16, 3-12 (1995).
terpinolene (0.22%) carvone(0.21o/o) Pace and R. Piccaglia, Choracterization of the essential oil of a
athujone (12.95o/o) caryophyllene oxide(0.96%) uilcl ltolia.n endemic sage: Saloia fficinalis L. aar. angustifolia
pthujone(10.89%) humuleneoxide| (2.21%) Ten. (Labiatae).J. Essent.Oil Res.,7,143-146 (7995).
menthone(0.11%) (13.46%)
viridiflorol P. R. Venskutonis,Essentialoil atmposition of somehet'bscultioatecl
camphor(10.36%) methylhexadecanoate(0.26%) in Lithuanio. In: Flatottrs. Frlgrlncis and Essential Oils.
linalool(0.26%) methyl(Z)-9-hexadecenoate Proceedingsof the 13th International Congress of Flavours,
acetate(2.24'/")
cr-fenchyl (0.06%) Fragrances and Essential Oils, Istanbul, Turkey, Oct. 1995,
B-caryophyllene(5.51%) manool(14.74"/") Edit., K. H. C. Baser,Vol. 2, pp. i08-123,AnadoluUniv. Press,
pulegone(0.86%) methyl(E)-9-octadecenoate trskisehir,Turkey (1995).
o,-humulene(9.72%) (0.11%)
borneol(3.81%) U. Ravld, E. Putievsly and I. Katzir, Stereochetnicalanaltlsi,sof
borneol in essential oilsusingpetnrcthyluted. ftcrlclodextrin as o
In 1985, Lawrence reported that the production of sage chiral statktna'ryphase.Flav. Fragr. J., ff, fgf-195 (1996).
oil in 1984 was ca. 40 tonnes. More recently, Boelens and f . Chane Ming, R. R. Vera and D. l. Fraisse,Compositionclel'huile
Boelens (1987) noted that the worldwide production oi' essertiellede sauge(Salxia fficinalis L. 1 de la Reunion. Ptiista
:1is oil had fallen to approximately25 tonnei. These same Ittrl. EPPOS, (Numero Speciale)615-649(1996)
iuthors described the odor of sage oil as being fresh- N. B. Perrv, A. J. Barter, N. J. Brennan, J. W. van Klink, j. A.
jrerbaceous,warm-spicy with a somewhqgcamphoraceous McGlimpsey, M. H. Douglas and D. Joulain, Drrlmatian sage
Patt 1. Difibring oil tliekls ancl.cornpositiortsfrom Jktoering
-haracter. They noted that the fresh herbal odor u'as anrl non-Jloueringacce,ssions. Flar'.Fragr.T.,f 1,23f -238 (1996).
:rirr:rarilydue to the cr- and B-thujone,ivhile camphor was
R. LAnger, Ch. Mechtler and J. Jurenitsch, Compo,sitionof the
:rs;lonsible for the camphoraceouschalacter.Furthermore, essentioloils of commercial sanples of Saluia o.fficinalis L. and
::'e\' noted that the slightly woody,'dry-out note was S.fruticosa Miller: A comparison Lf oils obtained bq ertroctiott
- -iusedbysesquitelpenoidcomponentssuchaso-humulene, and stean distillation. Phltocheln. Ana1.,7, 289-293 ( 1996)
: -caruophvlleneand viridifl orol.
C. Carta, M. D. L. Moretti and A. T. Peana,Actiaiht of the oil of
Salaia oJficinalis L. ogainst Botrqti,ecinerea. J. Essent. Oil Res., TableVll.Comparative chemicalcomposition(%)
8, 399-404(1996). of pentaneextractsof leaves,stemsand fruits
R. Piccaglia, M. M arotti and V. D ellaceca,Ej? ct of pl ant in g density of Foeniculum vulgare ssp. vulgare
and harcest dnte on yield ond chemical composition of sageoil.
]. Essent.Oil Res.,9, 187-191(1997). Leaf Stem Fruit
Compound extract extract extract
J. A. Pino, M. Estarron and V. Fuentes, Es,sentialoil of sage(Salaia
officinalis L.) groun in Cuba. J. Essent. Oil Res., S, 221-222 a-pinene 0.2 6.5
(ree7). myrcene 1.6 2.6 i,
M. H. Boelensand H. Boelens, Chemicalanclsensortleoaluationof o-phellandrene 30.3 16.2 I
th reesag t'.rils.Per f um . Flav or . . 22r2r . I 9- 40 r l9"9ir . p-cymene 0.6 1.4 I

limonene 0. 7
Fe nnel O il B-phellandrene c-I 6-t
octmene- 0.6
In 1990, Kreis et al. used enantiomeric separation on y-terpinene - o.,
a chiral capillary GC column to determine that the enan-
tiomeric ratios of o-pinene, B-pinene and limonene in allo-ocimene* 0.7
cis-sabinenehydrate U.J
fennel oil were: fenchone 10.2 S.6 to.Y

(S)-(-)-cr-pinen
e (2-3%): (R)-(+)-cr-pi
nene(97-98%) linalool 0. 7
(S)-(-)-F-pinene
(19-58%): (R)-(+)-B-pinene(42-81%) camphor 1.9 0. 8
(S)-(-)-l
imonen e (2-4'k): (R)-(+)-limonene
(96-980/0) borneol 0.8
methylchavicol 35.8 3 1. 7 oc. J
Two yearslater,Jeanet al. (1992)showedthat the sesquit-
(E)-anethole 5.4 4. 7
erpene hydrocarboncontent ofa fennel extractproduced by
1-(4-methoxyphenyl)
microwaveextractionwas below the level thev could detect.
-1-propanone** 0. 4
In contrast, an oil produced by hydrodiffusion containecl: o-ylangene o.2
germacrene
D (0.37%) (0.33%) 1-epi-bicyclosesqui-
B-caryophyllene
phellandrene 0.7
The following year, Lamarti et al. (1993) analyzed the
B-bourbonene 0-4
pentane extractofin-vitro cultivatedbitter fennel seedlings. neophytadiene 1.5 2.9
Using a combination of thin-layer chromatography,column methylhexadecanoate o.t
chromatography,GC and GC/MS, the authors determined methyloctadecanoate I
that the extract contained: methylpetroselinate 11

o-pinene(2.24o/o) cx{enchol(0.70%) hexadecanoicacid I

camphene(t) camphor(0.04%) petroselinic
acid 5 .8
sabinene(t) terpinen-4-ol(0.50%) pentacosane o.t
B-pinene(0.93%) o,{enchylaceiate(0.90%) heptacosane 0.3 0.8
myrcene(t)
cr-phellandrene (13.40o/")
carvone(0.05%)
methylchavicol(1.25o/")
squalene i,
henitriacontane 0.6
o-terpinene (0.10%) anisaldehyde(0.20%)
p-cymene(t) (Z)-anethole (1.80%) 'correct isomernot identified;." this compoundis not knownto the
B-phellandrene(0.40%) (E)-anethole (11.50%) reviewer;t = trace (< 0.1%)
limonene(1.63%) myristicin(1.70o/o)
y-terpinene(1.2470) (E)-isomyristicin(0.54%) ssp.Ttiperitum and hvo hybrids were analyzed by GC and
terpinolene (0.63%) (56.05%)
dillapiole
CC/MS. The results of these analysesare shown in Table
fenchone(0.88%) (E)-isodillapiole
(0.72%)
linalool(0.45%) apiole(2.10%) VIII.
Also in 1995,Agarwalcomparedthe major componentsof
t = tra ce (< 0 .0 1 %) oils derived from eight cultivars of F. uulgare ssp.oulgare
It should be noted that the seedling oil is very different grown in India. The major compoundswere as follows:
fro m f he oil olt he i ru i t. c-pinene(B-22-11.73%) (E)-anethole(64.27-70.40'/.)
A year later, Guillen and Manzanos (1994) analyzed a fenchone(10.59-11.66%)
seriesofpentane extractsand one oil produced from bitter Using multidimensional GC with one column being a
{'ennelfruit harvested from various locations in Soain. Bv chiral phase,Wang et al. (1995)determined that the enantio-
using GC and GC/MS astheir method o{analysisthe authors meric ratio of limonene in fennel oil was:
were able to show the ouantitative differences {bund be-
(4R)-(+)-limonene
(81.5%)
: (4S)-(-)-limonene
(18.5%)
tween these various samples analy?ed. Their results are
summarizedin Table VIL \,r Zygadlo et al. (1995) screeneda number of oils for their
In 1995, Badoc et al. were able to successfullyobtain antioxidant activity. An oil of Fl uulgare var.dulce was shown
hybrids between Foeniculam Dulgare ssp.piperitunn. (male to possessa moderate antioxidant activity. The major con-
sterile) and F. oulgare ssp. aulgare. Oils from the parent stituents of this oil were as follows:
 TableVlll.Comparativechemicalcomposition(%)
ot Foeniculumvulgare ssp.piperitimtiuii oil Table lX. Comparative chemical composition
(%) of
and two hybridfruit oils oils of various parts of the fennet plani

Compound Leaf oil Flower oil

ssp. piperitum HybridA Hybrid B Fruit oil Stem oil
Compound oil oil 0-ptnene
oil 7.2 5.0 It.3 1 .9
cI-plnene sabinene
0 .6 1 1 .2 zJ- I
I I t I
camphene cr-phellandrene 8.8 6.7
0 .7 0.6 2. 4
sabinene o-terpinene 0.1 ' 1.9
0 .2 0 .7 0.4 z .z 0. 2
B-pinene 0 .7 1.2 limonene**+
myrcene 0 .8 B-phellandrene 9 . 6 20.7 3.7
2 .6 I.b (Z)-B-ocimene
LC
a-phellandrene 0 .4 0 .7 0.6 0.9 0.4
p-cymene
0.8 (E)-B-ocimene
T
7 .2 0 .2 0 .4
I I t I
lrmon en e 5 6 .6 1 7 .1 terpinolene
I c-z t t rt
fenchone 9.6 5.0
7-terpinene AO 4.0 7.2 6.5
fenchone methylchavicol 2.0
0 .3 3 7 .0 3 6.5 LC 1.7 2 .4
terpinolene (E)-anethote 60.0 50.9
9 .2 0 .2 0.2 50.1 73.6
campnor 0 .1 0 .8 germacreneD
0 .5 0.9 0.3 0.2 t
methylchavicol 0 .9 -" majorcomponentof mixedpeak
(E)-anethote 0 .3 1 7 .1 t = trace (< 0.1%)
1 0 .9
piperitenone 0 .8 0.4 o.4
piperitenoneoxide 1 4 .1 0.2 0 .9
Although he found that all parts were rich in
myristicin 3.4 ]:!t,hri"t".
0.9 (r-l-anethole, the content was highest
in the stems (Table
Overall, however, the oil coitent of fennel
.IX). stems was
a-prnene(3.2%) less than 0.27o.
citral-(1.5%)
a-phellandrene (2.9%) methylchavicot(5.0%) The following year, Guillen and Manzanos (1gg6)
Irmonene
re_
(2.0%) (E)-anethole(7O.O"/") ported the resultsofan analysisofthe pentane
f en ch on e(1 .1% ) extractso{.the
carvacrol(1.3%) leaves,stemsand fruits of _Eaulgareirp.
udgornthat origi_
- correct isomer not identitied nated in the Basque region of"Spaln.'fablE
X shows the
componentsidentified in these,r^iio.,, extracts
\-enskutonis(1995) compared the composition by a combi_
, of some nation of GC and GC/MS.
.b-distilled oils from varioui parts of the feiinel
plant grown This same year, Bernath et al. (1996)
compared the

TabreX. comparativechemicarcomposition(o/o)
of variousfruit extractsand
one oir of Foenicurumvurgaressp. iurgarefrom the
Basqueregion of Spain
Extract Extract Extract Extract
trom Essential Extract Extract Extract
from from from oil from
Compound ulivarri-Gamboa Lasarte from from from
Arroyabe n,|enolaoula nr"noii"il"r" a""" Laguardia Berantevilla
:spinene 1 ,8 t 2.1 1.9 0.2
:amphene 0 .2 1.9 o.2 0.5
- 0.4 0.5 1
3aotnene 0.2 0.5 I t
- 0.6 0.2 0.1
-yrcene 1 .0 0.7 0.1 0.4
1 1.1 t. I 0.3 1.1 0.5 0.6
:-chellandrene 0 .5 0.9
:-cymene I
-onen e
I
t t t
3 .8 I
',-;erptnene 1.7 10.7 4.5 4. 2
0 .9 0.5 0.4 0.7 o.4 0. 2
hydrate- 1
=:-,ahone
-,:lrnene
t t rt
25.9 t
:a ool z t.c 17.7 25.8 16.9
I 20.2
0.1 t tt
:a-DnOr 0. 5 0 .2
0.4 0.6 0.7
*€:nyl 0.3 0 .4
chavicol 64.1 rFiq.s 59.3 48.7 48.6
Z -anethole o t.J 50.4
t I I
JJ. /

i -anethole ne 1 I
2 .8 22.5 28.8
-E:-yl petroselinate
0 .7
24.7 ,:a 38. 5
trt
j-r::Sltane
0 .5 0 .9 0.2 o.4 ne 0.4 0.6
r:-:ct rsomernot identified;t = trace (< 0.1
%)
mor?hology and chemistry of 13 populations of F. oulgore (E)-anethole(52.65%) (0.15%)
B-bisabolene
germacreneD (0.33%) (0.12'/.)
E-cadinene
var. oulgare. Seeds of these 13 populations (four Italian
cultivars,one French, one Korean,one Belgian,one Hungar- A sample of F. oulgare fruit oil of Uzbek origin was
ian 'soroksari' and five cultivars of unknown origin) were analyzedby both GC and GCiMS and found (Baser et al.
planted in an erperimental garden in Budapest. Oils pro- 1997) to contain the following major constituents:
duced from these cultivars grown over two seasonswere
limonene(0.78'/.) methylchavicol(3.24'/.)
found to contain the following major constituents: (0.39%) (E)-anethole(87.33%)
B-terpinene
(0-3.5%)
ct-pinene fenchone(7.5-42.4%) fenchone(8.03%)
B-pinene(0-2.2%) methylchavicol(2.6-43.5"/")
(E)-anethole(20.9-85.7%)
The fenchone content of this oil suggestsit is from bitter
( 0. 9- 16. 5 % )
Ii m onene
fennel.
As can be seenfrom these results,the oil composition o{' Also in 1997, Badoc and Lamarti (1997) summarizedthe
these various cultivars varied significantly. The authors also information that is known on Foeniculam aul gar e M ill. They
analyzed oils produced from different organs of three of noted that the speciescould be subdivided as follows:
these cultivars,the resultsof which can be seenin Table XI. ssp.piperitum
(Ugria)Cout.
The authorsthen subdividedthe Fl culgare ssp.capillaceum ssp.vulgarevar. vulgare
var.au,lgareinto the chemical forms shown in Table XII and ssp.vulgarevar.azoricum (Mill.)Thell.
ssp.vulgarevar. dulce(Mill.)Thell.
used cluster analysisto classifythe chemovarietiesshown
th e re. Fruit oils of F. oulgare ssp.piperitum are characterizedby
AIsoin 1996,Venskutoniset al. usedboth GC and GC/MS small amounts of (E)-anethole, large amounts of limonene
to analyze an oil obtained from the flowering pafts of and y-terpinene, and by the presence of piperitenone and
bitter fennel grown in Lithuania. They reported that the oil piperitenone oxide. Fruit oils of E oulgare ssp.aulgare can
contained: be either rich in myristicin or rich in methyl chavicolor (E)-
o-pinene(4.08%) lim onene( 10. 31% ) anethole.Fruit oils of F, aulgare ssp.uulgarevar.aulgareare
camphene(0.13%) (Z)-B-ocimene (0.77o/o) rich in methyl chavicoland,/or(E)-anetholewith substantial
sabinene(0.22%) Tterpinene(0.81%) amountsoffenchone. Fruit oils ofF. oulgare ssp.oulgarevar.
B-pinene(0.33%) fenchone(15.59%) azoricum contain low levels of methyl chavicol. Finally, fruit
myrcene(1.25'/.) terpinolene (0.10%)
oils of E oulgare ssp.aulgare v ar.dulce are rich in either (E )-
(6.15%)
o-phellandrene camphor(0.21%)
p-cymene(1.21%) methylchavicol(2.73%) anethole or methyl chavicol, with low levels of fenchone.
(0.82%)
B-phellandrene anisaldehyde(0.29'/.) In 1997,Bartschatet al. (1997a)developeda multidimen-

Table Xl. Comparative maior component composition (%) of various organs of three cultivars of bitter fennel

Stem Leaf Bud Flower Waxy seed Ripe seed

Compound oil oil oil oil oil oil

s-prnene 4. 4- 11. 3 6. 5- 21. 8 5.7-8.5 5.1-7.3 1.5-2.0 0.8-1.6

Iimonene 3. 5- 10. 1 1. 2- 11. 9 10.7-20.6 6.3-7.3 | . t- z .z 1.4-2.3
fenchone 3.2-9.0 t - 11. 5 1.9-13.8 4.8-32.7 12.8-23.5 12.7-26.1
methylchavicol 2.4-2-6 2. 1- 2. 7 1.9-3.3 2.0-2.7 3 . 1- 6 . 5 2.7-3.9
(E)-anethole 64.6-69.8 46.4-57.3 47.3-56.6 39.0-67.5 71.6-77.3 66"5-76.6

t = t r a c e( < 0 . 1 % )

Tabfe Xlf. Chemical forms of 13 cultivars ol Foeniculum vulgare ssp. capillaceumvar. vulgare

MethYl
Anethole chavicol Fenchone
Ghemovariety Chemoform (7"\ (/") (%l

A: highanethole,low methylchavicol >66.5 2-7-6.5

(E)-anethole B: middleanethole,highmethylchavicol >63.5 12.5-15'0
C: low anethole.low methylchavicol >60.0 2.6-5.6
D: middleanethole,highmethylchavicoland fenchone >62.1 8.2-15.0 16.3-24.9

fenchone >30

methylchavicol
 sional GC/MS technique to simultaneouslv differentiate D. Bartschat,M.Wiist, H. HanssumandA. Mosandl,Staraoisomeri,c
between the eight enanti,omersof 3-bugrl hexahydrophthalide. Jlaaor compounds LXXXII :3-butylhexahydrophthalides : Simal-
Using this technique, Bartschatet al. (1gg7b) examinedthe taneous enantioselectioe analqsis, structure elucidation ancl
sensurialproperlies of the siet.eoisum?rs. High Resolut.
enantiomeric distribution of 3-butyl phthalides and 3-butyl J.
Chromatogr.. 20. 251-257 ( 1997a1.
hexahydrophthalides in finocchio (F, oulgare ssp. uulgare
D. Bartschat, T. Beek and A. Mosandi, Stereoisomericflato,r
var. azoricurn). they found the following enantiomeric compounds 79. Simultaneous enantioselectioe analqsls of 3-
distribution: butylphthali"de and 3-butyl hexahydrophthaLide staieoisoiw rs
in celery, celeriacandfennel. J. Agric. Food Chem., 4E,4EE4-
(3S)-butyl
phthalide
(36%): (3R)-butyt
phthatide
(64%) 4557(ree7b).
(3R,3AR,7AS)-butyl
hexahydrophthatide(>99%)

P. Kreis,U. HenerandA. Mosandl,Chiralelnholtstffi titherischer Cardamom Oil

Ole; Ul. Stereoclffi renzienrnguontx-1tinen,
ftpinin ancllimnnen Analysisof the basicfraction of cardamomoil by a combina-
i1 Ol9n,drogenundfenigarzieimitteln Deut. Apoth.Ztg., LJO,
eB5-988 (1990). tion of preparative GC, 1H-NMR and MS (Maurer and
Hauser 1992) revealed the presence of (Z)-3-(I-butenyl)
F. I. Jean,G. J. Collin and D. Lord, Essentialoilsand microuaae
extractsof cultiaatedplants. Perfum. Flavor., f7(3), 35-545 pyridine in ppm levels.
(1ee2). Two years later, Gopalakrishnan (1994) compared the
A. Lamarti, A. Badoc and J. F. P. Carde, Etude chrotnatographique changesthat take place in the major constituentsof liquid
de I'huile essentiellede la plantule defenouil amer (Foeniculum COr-extractedcardamomwith that of commerciallydistilled
aulgare Mill.); caractdristiques spectrales (W, lR, SM) de ses oil asthe products are stored at ambient temperaturesfor up
constihtents.Bull. Soc.Pharm. Bordeaux,f32, 73-Sg (fgg3).
to 90 days. The components of the oils and extractswere
M. D._Guillenand M. J. Manzanos,Acontributionto study Spanish characterizedby GC only; however,all had been previously
u;ild-growing fennel (Foenianlum atlgare MiIl.) as a"source of
confirmed as cardamom oil constituents. The analltical
Jlaaour compounds. Chem. Mikrobiol. Technol. Lebensmitt.,
r6(5i6), 141-145(1994). resultsofthis studycanbe seenin TableXIII. Gopalakrishnan
A. Badoc, A. Lamarti, G. Bourgeois,j. P. Carde and G. Def{ieux, concluded that even though COo extractsof cardamom are
Hybridation intrasp dcifique chez lefenouil, F oeniculant oulgare of better quality than the oil whln fresh, they were found
Mill. BdI. Soc. Pharn'r.Bordeaux,tB4, 107-126(1995). to deterioratefasterthan the oil.
S A^garwaf,Volatile oil constituents in different entries of fruits of The following year, Ravid et al. (1995) determined that
fennel (F. aulgare).IndianPerfum.,39(2),70-71(1995). the enantiomeric distribution of cx-terpineol (5.8Vo)in a
X-H. Wang, C-R. Jia and H. Wan, The direct chiral separation of commercial sample of cardamom oil was:
some optically actiae compounds in essential oils by multi-
climensional gaschronLatography . l. Chr omatogr. Sci., 59, 22-25 (4R)-(+)-o{erpineol
(87%): (4S)-(-)-orerpineol
(13%)
(1 99 5).
Also in 1995,Variyarand Bandyopadhyayreportedthat an
J A. Zygadlo, A. L. Mararque, D. M. Maestri and N. R. Grosso, oil of Indian cardamom produced bv simultaneousdistilla-
Empleo de aceitesesencialescomoantioxidantesnaturales. Grasas
Aceites,46, 285-288 (1995).
P, R. Venskutonis,Essentialoil comltosition of someherbs cultioated
in Lithuania. In: Flauours. Fragrancis and Essential Oils. Table Xlll. Comparativechanges in the chemical
Proceedingsof the 13th International Congress of Flavours, composition (7.) of oils and liquid GO, extracts
Fragrances and Essential Oils, Istanbul, Turkey, Oct. 19g5. of Indian cardamom
trdit., K. H. C. Baser,Vol 2, pp 108-123,Anadolu Univ. Press,
Eshsehir, Turkey (1995). CO, extract Essential oil
\I. D. Guillen and M. j. Manzanos,A study of seaeralparts of
Compound Fresh 90 days Fresh 90 days
the_plant,Foeniculam aulgare as a sourci oj compounds with
industrial interest.Food Res.International, 29, 85-88 (1996). 0,-prnene 0.7 0.5 2.3 0. 6
J. Bernath, E. Nemeth, A. Kattaa and E. Hethelyi, Mo:hological B-pinene 4.3 2.0 6.2 2. 5
and chemical euafuation of fennel (Foeniculum aulgare l,,Illl.) sabinene 2.8 1.4 +.2 t.o

populations of dffirent origin. I. Essent. Oil Res., g, Z+I-ZSS limonene z,J t.5 4.0 2.7
( 199 6). 1,8-cineole 27.0 21.8 38.8 27.8
P. R. Vensk-utonis,A. Dapkevicius and T. A. van Beek, Essential oils linalool 3.9 3.3 5.7 5 .3
of fennel (F oenicufum oulgare M ill.) fron Lithu ania. J. Essent. terpinen-4-ol 2.0 2.1 2.0 3 .2
Oil Res.,8, 21r-2f3 (1996). c)[-terpineol 5.9 5.5 3.4 3.3
K H. C. Baser,T. Ozek, Kh. R. Nuriddinov, A. M. Nigmatullaev,K. linalylacetate t"c l./ 1.0 1 .7
Kh. Khadzimatov and Kh. N. Aripov, E#ential oils of Mediasia geraniol 0.4 0.5 0.2 0 .3
rnacrophylla (Regelet Schmalh) Pimen. and,Foeniculum uulgare o{erpinyl acetate 40.9 49.4 24.6 43.3
\LilL.fromLlzbekistan. J. Essent.Oil Res.,9, 249-250 (1997). geranylacetate 0.6 1.1 0.8 1 .3
\. BadocandA .Lamafir, Contribution dl'€tude du genreFoenicularn nerolidol- l-J t 0 .5
7till. Irr: Proceed)ngsAromatiques et i,Iediciniles et leurs huiles
t correct
essentielles.Edits., B. Beniilali, M. trttalibi, M. Ismaiii-Alaoui isomernot identified
andZ.Zira,pp. 21-36 AceiesEditiot'rs,Rabat,Morocco (1997). t = trace(< 0.1%)
tion and extraction( Likens-Nickersonapparatus) was found Boldo Leaf Oil
to contain: Boldo, a small, evergreen doiecioustree native to Chile, is
o(-pinene (0.4%) linalylacetate(4"6%) taxonomicallyclassifiedasPeumusboklas Mol. According to
sabinene(1.4%) crterpineol(2.7%) Vogel et al. (1996), essentialoil content is allected by light
m yrce ne(1 .2% ) geraniol(2.5%)
intensity,leafage, seasonand sexofthe tree. The highest oil
1,8-cineole (24.7%) nerol(0.9%)
limonene(0.9%) crterpinylacetate(49.0%)
yieldsare obtainedfrom young leavesharvestedfrom shaded
linalool(5.8%) B-caryophyllene (0.4%) male trees in June (winter).
terpinen-4-ol (1.9%) nerolidol-(1.2%) Also in 1996, Miraldi et al. in Italy hydrodistllled boldo
leavesof Chilean origin and boldo leavesof Italian origin.
The oilswere subjectedto analysisby GC/MS and the results
B. Maurer and A. Hauser , New pqricline deriuatiuesfron e.ssential of these analysescan be seen in Table XI\2.
oils. Chimia,46, 93-95(1992).
H. Vogel,I. Razmilic,U. Doll anclR. Rdz,Variability of someactixe
N. Gopalakrishnan, Stuclieson the storage quality of COrextracted
contpounclsin Boldo (PeunrusbolclasMol). ln: Proceeding,s
carclantom and clot:e bucloil,s.j. Agric. Food Chem., 4 2, 796-798
(1ee4). Inte'rntrtionalStlmpo,siun BreedingResearclLon MedicinalaruJ
ArornoticPlanrs.Edit.,F. Pank,pp 364-367, FederalCentrefor
U. Ravid, E. Putievslqr and I. Katzir, Determination of the BreedingResearch on Cultivatedplants,Quedlinburg(1996).
enantionwric compositktn of a-tetpineol in essential oils. Flar'.
E. Miraldi,S. Ferri, G. G. Franchiand G. Giorgi,Peunru,s boldus
Fragr.J., r0,281-284 (1995).
essentialoil: Neu'cortstituents
artdcomparisonof oilsfrotnleaaes
P. S. Varlyar and C. Bandyopadhyay, On the oolatiles of cloue, of differentongin.Fitoterapia, 67, 227-230(1996).
car damorn, rruhneg and rnace. PAF Al, (jan/M ar.), I 9-25 ( I 995).

Table XlV. Percentagecomposition (%) of Boldo leaf oil produced from ltalianand Chilean leaves

Italian Chilean Italian Chilean Italian Chilean

Compound leafoil leafoil Compound leaf oil leaf oil Compound leaf oil leaf oil

2-heptanone 0.06 0.03 terpinen-4-ylacetate 0.03 0.02 a-fenchyiacetate 0.06 0.04

d-thujene 0.06 0.03 linalool t cuminaldehyde 0.18 0 .1 0
d-prnene 0 .0 2 0 .0 1 2-nonanol t t geraniol 0.09 0 "1 0
crjenchene 0 .0 2 0 .0 1 0-thuJone 14.30 ascaridole 38.63 21.25

camphene 0 .3 8 0 .2 1 o,{enchylalcohol 0.40 0.22 cis-verbenylacetate O.14 0.08

saDrnene 0 .0 4 0 .0 1 B{hujone t | . t3 thymol 0.07 0.03
myrcene 0 .0 2 0 .0 1 frans-pinocarveol 1.20 0.66 sabinylacetate. 4.28 2"36
a-phellandrene 0.04 cis-verbenol t 9.90 carvacrol 0.01

6-3-carene 0 .2 5 0 .1 4 camphor 0.06 0.01 trans-cawylacetate 0.08 0.04

1,4-cineole 0.92 0.51 B-terpineol" 0.13 0.07 thymylacetate 0.03 0.01
cr-terpinene 0.04 0.02 terpinen-4-ol 1.37 0.75 methyleugenol - 0.75
p-cymene 9 .5 1 8 .6 3 crterpineol 0.25 0.14 ledol 0,32 O.1 7

ilmonene 0.07 0.04 myrtenal t guarazulene 8.80

1A-ninonlo 38.63 21.10 sabinakeione 0.78 o.4
fenchone 0 .0 1 t myrtenol 0.36 0.20
2-nonanone 0 .1 0 0 .0 4 nerol 0.07 0.04

* correctisomernot identified
t = t r a c e( < 0 . 0 1 % )