chapteb h i

CCMPQSITIQU Uj V ifil iTIONS III ESSENTI aL OILS

The composition of essential oils varies not only from

species to species, but also in a single spec!as

belonging to different geographical regions*

Variations in the composition of terpenoids, in particular,

have been of great significance in the study of

chemo-taxonomy and bio-chemical systematica*

Observations have revealed that in a single plant species

the composition of ethereal oils can differ from one

part of the plant and the other* such variations occur

because of changes in the ecological conditions, such as

soil, cli iate, and altitude* These variations also

occur with the development of the plant*

This chapter traces some developments in the study

of compositional variations in essential oils and

presents the observed changes in the compositions of

the oils of Thymus serpyllum L*, Tagetus minuta L*,

and skimmia 1aureola 3 & Z*

ISO

in* i xateteMaa

In 1333, Si ever s and ijowaun found that with the

growth and development of Mentha arvensis there was a

considerable change in its oil content* Correspondingly

there was a change in the menthol content and ester2number of the oil* Charabot studied variations in the

composition of essential oils of lavandula, Mentha

piperita. Artemisia, and pelargonium and arrived at

similar conclusions* 4 careful study of the influence

of environment on the composition of Eucalyptus cneorl folia3

was maae fey Berry, et.al* They found that there was

no difference in the oil content of matured leaves,

but there was considerable difference in their oil

content and the properties of these oils, during the4

early stages of plant development* Malin^re investigated

changes in the composition of the volatile oil of

Mentha piperita at various stages of its development*

Maarse and Kepner studied compositional changes in

the oil of Douglas fir* on the basis of similar studies,6

Maarse derived the hypothetical biogenesis of terpenoids

in origanum vulgare* Kalin^re derived the biogenesis

of the oil of Mentha piperita in a similar manner*7

y&es, et*al investigated variations in the essential

oil of Pinus merkussil.caused by geographical variations,

and suggested that these differences provide a strong

support for the observed morphological changes in the plant

1

The influence of climate on the biogenesis of tea flavour

has been studied by Wicfcremansin^e, who related the

observed variations to the decree of carbon dioxide

fixation and to intra—and axtra— chloropldstidic9

biosynthetic reactions* Hefendehl and Murray have

recently studied changes in the composition of

Mentha aauatlca by gene substitution from other mint

species| they have also formulated a biogenetic schemeID

for the terpenoids of this oil* Zavarin and Snajberk

have differentiated between four races of Douglas fir

oa t&© basis of differences in the coaposition of its

volatile oil* They found that similar variations occured11

in the hydrocarbon fraction of j&kjs Mk»dasa(i-) M*,

and differentiated between four species of this plant*

They also attempted the biogenesis of longlfolene and12

longlc/cline* Razdan and Koul studied changes in the

yield percentage and composition of thyme oil*

III.2

Thymus aarpyllua L* was procured during 1973 and

1974, at different stages of development, from four sites

in Kashmir province, Jjunto* and lUshmir state (India)t

Site 1 — Shankaracharya hill, in the heart of the

city of Srinagar| altitude, 1700 m*,

Site II Harwan, 13 Kms. north-east of Srinagar)

altitude, l^SOi*,

1B1

IS 3

Site III — Baraaulla, 66 Kms. vest of Srinagar*

altitude, 1200 a ., and

Site Ilf — Tangaarg, 34 Kms. south-west of Srinagar*

altitude, 3971m.

The seeds of Taaetus ml nut a. were collected during

December from the plants growing wild in the campus of

the University of Kashmir, and were successfully grown

the next year at four soils having different

soil characteristics• The seeds were procured from

cultivated plants during November and December, 1975.

1&e leaves of ski mmi \ laureola were collected from

Oalmarg, during the months of April, June, and September.

The raw material was transported in sealed

air-tight bags. The flowers, leaves, and stoma of

Thymus sarrtvllum were separated mechanically. Before

distillation the plant material was exposed to air at

room temperature for 72 hours, similarly the leaves

of sidlmmia and the seeds of Tagetus were also exposed

to air for 24 hours. Thyme oil was obtained by

water-steam distillation of the plant materi.il and the

oils from Tagetus and s&iaaala were obtained by ste*m

distillation. The volatile oils were dried over

anhydrous KBSO4 and, after determining their physical

properties, were stored as petroleum ether or ethanol

solutions till they were subjected to chromatography

( 4.0 • , T • L.C. , and G. JL»«C .) •

I I . 2 * i i S O U A B a lV S if l

The analysis of the root soils was undertaken in

accordance with the procedures outlined by r iper and13

Jackson* 4 brief outline of the various procedures

adopted during the present analysis is given below*

After determining the soil texture of various

soil samples, their moisture content was found byo

drying 20 <£&s* of each sample in an oven it 60 C*

Determination of pg and Conductivity of Soils

I£3

The pg and conductivity of soils was determined

by preparing a suspension of soil in water (ratio, 1x4)*

p was measured on meter, type PE 9406, V§0, s*Ho*1304f

and conductivity was measured on Toshniawal conductivity

meter, type CL 02/014. s.Ho. 227*

Butchinson*s method was employed for determining

the percentage of carbonate in various soils, and it was

calculated as *»2

% CO3 * (B - T) x W x H x 0. 003, *&©re

B * vol. of acid used in blank titration,

T « vol. of acid used in normal titration,

N = normality of acid, and

W * weight of dry soil*

Nitrogen was determined by modi fled KJeldahl's

method* Each soil sample (10 gas.) was treated with

HagS04~«*CuS04—Se (20*3ii) and 60*6 blLs, of conc* H^G4*

The mixture was digested for one hour till a ll«£vfc yellow

solution was obtained* The flask was subtly eooled

and its contents were diluted with 60 mis* of

distilled water$ it was cooled again and 4Qi solution

of sodium hydroxide was added to it to liberate

ammonia, which was distilled into 5 mis. of boric

acid solution* oromoeresol-green and methyl-red were

used as indicators and boric acid was bacK-titrated

with standard acid solution till the blue colour

disappeared* The percentage of nitrogen was calculated

from the formula

% N * (T * B) x H x 0*14, where

T a vol. of standard acid used In normal titration,

B = vol. of standard acid used in blank titration,

N * normality of acid, and

0*14 * titration factor per 10 gms* of soil sample x 100*

aX s&sjaaa

The total carbon content of each soil sample was

determined by calculating the loss in their welgit on

ignition in a furnace* Their oi- janie matter was

determined by chromic acid method*

IBS

0*25 @as* of every soil Simple was treated with

20 mis. of 0*4 N chromic acid and was heated, with

stirring at lj55°C for half an hour. The mixture was

cooled and diluted with 75 mis. of water.

Ortho-phenanthroline (ferroin) solution was added as

an indicator after adding & mis. of phosphoric acid,

m e solution was bacio titrated with 0 .2 N ferrous

ammonium sulphate till the solution turned red.

A blank experiment was run simultaneously and the

percentage of organic matter was calculated as*

% organic matter = 20 x ( i - -X ) x 0.92$ wheresT * vol. of 0 .2 8 Fe(HH^)g (S04 >2* ® used in

sample titration and

S « vol. of 0 .2 H Fe<®4 ) 2 (S04) 2* 6 used in

blank titration.

a£ Sfes ZM&m%msl si Sl*1iat2a

The pg of the water extract of each soil sample

( 2x1) was made up to ^ 3 .2 by using 0 .1 H H^>04 or

O . I H H a ^ 0 3 solution. 0 .5 N AgSOg was added to

precipitate silver chloride. The precipitate was

filtered on sinetered crucible and was washed* and

dried at 140 °C for two hours* if ter welding the

precipitate the percentage of chloride anions was

calculated ass

336

% chloride * W x 0*2474 x • t whereS ’W « weight of the precipitate,

S * weight of the soil sample, and

0*2474 * gravimetric factor*

a£ & & j££salm s s£ §&iaia.te uaiaja*

She water extract of each soil sample was

acidified with. 0*3 N HC1 and boiled, and BaCl solution

was added to precipitate barium sulphate.

The precipitate was filtered, cashed, dried, and 1 jolted*

The percentage of sulphate ions was calculated ass

inn% sulphate anions * W x 0*4120 x — ; where

S

VI at wei^it of the precipitate,

S « wei^it of the soil sample, and

0*4120 * gravimetric factor*

ftaifaaUM ltea at SM M t o ls

50 gas* of each soil sample was shaken with

extraction solution, prepared by mixing 200 mis. of

1 N CuSO^ solution, 0*6% silver sulphate solution,

and water* 0*4 gms* of C a (d isso lu tio n )was added to

it with constant shaking* It was followed by the

addition of 1 ga* M<£03* The suspension was filtered

and the filtrate was evaporated to dryness*

Hltrophenol disul phonic acid solution was used to

develop its colour and the percentage of nitrate anions

was determined colorimetric ally at 420 sp and comparing

it with standard curves*

137

ftstarmMfcksa al SM tssaaStua. M v.atAsafe

4 welded quantity of each soil sample was shaken

with 1 N NH .OAC solution and filtered* The filtrate 4

was evaporated to dryness, treated with ZQ% HgOg,

refluxed for half an hour, and again evaporated to

dryness, m e residue was treated with lQi> NaOH and two

to three drops of phenolphthalein were added* It was

+1again evaporated to dryness to remove ions*

The residue was treated with 1 N HC1 and again evaporated

to dryness* it was dissolved in 0*1 N aeetic acid ,

containing 4* formaldehyde, and was later centrifuged*

ifter centrifugation the solution was treated with

20$ sodium cobaltinitrite solution at 3°C to precipitate

potassium cob&ltinitrite. The precipitate was allowed

to stand overni^xt and filtered through sintered

crucible, washed, and dried at 100°C for 10 mins*

The percentage of potassium was calculated ass

% potassium (ag* ©q*) » W x 0*425 $ where

W » wei^tit of the precipitate and

0*425 » gravimetric factor per 10 gms* of the soil

sample x 100*

al Mm. gM fJaasM

i w elded quantity of each soil sample was fused

with sodium carbonate and dissolved in distilled water.

The suspension was filtered, the filtrate was neutralised

with 1 ■ V ° 4 * 3 ) , and the volume made up to 50 mis.

The percentage of phosphorus w*s determined

colorlmetrieally using Busch and Lomb spectrophotometer

after developing blue colour with sulphomolybdlc acid

and reading percentage transmittance at 660 spu

The blank experiment was carried out with potassium-

dihy dr ogen-phosphate •

aafe&ma,4t>4.Qa si satetoa saataat

50 $&&• of each air-dried soil sample was shaken

with 100 mis. of ME^04c solution and after allowing it

to stand overnigat the suspension was filtered and

leached with HH^Oac* The filtrate wat* evaporated to

dryness and the residue oxidised with 2 mis* of H ^)g.

2 mis. of 6 N EH0o were added to the resultant

solution which was digested on a water bath for half

an hour, and was again evaporated to dryness.

10 mis. of 6 N HCl were added to the residue* the resultant mixture was diluted with 10 mis* of

distilled water, filtered, and washed. The volume of the filtrate and washings was made up to 100 mis.

From the above solution, calcium was precipitated

as calcium oxalate under alkaline conditions. The precipitate of calcium oxalate was washed with a small quantity of dilute ammonium hydroxide solution, and

dried* It was ignited to give calcium oxide and

cooled. The precipitate was dissolved in dilute

hydrochloric acid and the solution was titrated with

0*5 N potassium permagnate solution* The percentage

of calcium was calculated ass

% calcium * V x 0*666 $ v&ere

V ■ vol* of 0*5 N KMnO^ solution used and

0*666 * volumetric factor*

MMK R kQSk fll tt4flM»AMI £.2flfcgfl*

The filtrate left after the precipitation of

calcium oxalate was nude alkaline with *ai4O0 (pg 6*2)

and bromocresol purple was used as an indicator*

The filtrate was heated on a water bath and 20 mis*

of 10% ammonium hydrogen phosphate were added to it

slowly* The solution was made more alkaline by

adding 30 nils, of concentrated solution to it*

The mixture was stirred till magnesium hydrogen phosphate

precipitated out* It was filtered, washed, dried,

and ignited to get magnesium pyrophosphate.

The percentage of magnesium was calculated ast

% magnesium * W x 0*239 $ where

W * weijit of magnesium pyrophosphate and

0*220 » gravimetric factor per 10 £&s* of the

soil sample x 100*

.ftitf.yMMl4.Sfl il J&s koaisai

The ammonium acetate extract of each soil sample

was treated with 15 mis* of magnesium-uranyl-acetate

reagent (prepared from uranyl acetate and magnesium acetate

200

andaagnesiUia acetate (ls3sl) solution in water, followed by the addition of glacial acetic acid and 96tf ethyl alcohol), stirred* and allowed to stand for 1.5 hours* Tne precipitate of sodium-magnesium-uranyl- aeetate Wi» filtered over sintered crucible, washed with <1 mis* of 9&* ethyl alcohol, and dried# Ihe precipitate was veiled and the percentage of sodium was caxculatea asi

% sodium (exchangeable eq« ) » w x &£•& | where W » wei^it of the precipitate and52*5 m gravimetric factor per 1G jaa. of the soil

Saapl® X 100*

m.a.iii .mMjcsii ai m j k m t k s i m &

Depending on the amount of the essential oil obtained during each collection of the plant, the oils were analysed by column chromatography and Tie or by 0»X»C*,ln accordance with the procedures outlined in chapter II (p*9ojl62). fhe percentab@ composition of each oil presented her© is based on o*I«C* data*

191

111.3*1 Volitions iq the Composition of the Oil of Thymus serpyllum Linn.

In Kashmir Thymus serpyllum l . bears highestessence during morning hours) It Increases graduallytill the maturation of the plant* The favourableclimatic conditions for title development of the essence

oare sunny days (max. temp. 20 to 30 C ) followed by clear nl^its with moderate temperatures (S to 16°C).The flavour of the plant diminishes during rainy days.

Two crops of Thymus aerpyllum L. are producedannually. The *Spring crop* extends from late Februaryto July, when the average maximum and minimum

o otemperature rises steadily (8 C to 30 C) with anaverage li^it period of 9 to 14 hours, and the♦Winter crop* extends from early September to themiddle of December, when the average maximum and

o ominimum temperature falls from 20 C to 7 C with an average li^it period of ten to six hours. These two crops seem to be governed by li<£it and temperature factors) the spring crop is a hl<£x temperature-long day plant and the winter crop is a hi^h temperature- low temperature intermediate form. The flowering of the plants is uneven and takes place earlier at rich miner.il containing basic soils, preferably at lower

I I I .3 Hesults and Discussion

altitudes than at other soils. The characteristics of various soils are presented in table XXX*1 and the phonological data of the plant is given in table XXI.2.

l& M U m * la jM at

the oil

The yield percentage of sixty four samples of the oil is given in Fig. XXX. 1 and the physicochemical properties of these oils are tabulated in tables XXX.3 (leaf and flower oils) and III.4 (stem oils). Stems contain lesser quantities of the oil than leaves and flowers.

The plants show considerable variations in their essential oil content with changes in the quality of the soil, the altitude of the substratum, and the development of the plant (Fig. III.l). The crop yield as well as tiie yield of its essential oil is maximum at ba&dc mineral-rich soils, preferably at low altitudes (1 to 1,52% ia leaves and flowers, and0.49 to Q.,59% in stems). Second crop yields more plant material than the first crop and the percentage of essential oil is also higher daring this crop.The oil content increases gradually with the growth of the plant and is maximum when it is two to three months old. The formation of the oil in the plant is favoured more at basic soils than at acidic soils. During the

192

YEILD

PE

RCEN

T1-20-

10

i-00

0*90

0*80

0-70

0-60

0-50

0-40 - *

MARCH APRIL MAY JUNE SEPT. OCT. NOV. DEC.

FIG.Ill I. YEILD VARIATION IN LEAF AND FLOWER AND STEM OILS OF CTHYMUS SERPYLLUM L.)

VARIATION IN LEAF AND FLOWER OIL —VARIATION IN STEM O I L --------- ►

o ---- SITE NO. Ia -- - SITE NO. 2□ -- - SITE NO. 3x -- - SITE NO 4

193

first crop there is no appreciable increase in the oil content of the plant after the age of three months. However, daring the second crop, except for the plants belonging to hi#i mineral containing soils (site II), the formation of the oil continues till the maturation of the seeds.

The oils obtained from the plants growing at acidic soils are lifter and less optically active than the oils obtained from the plants thriving at fertile soils, second crop yields slightly heavier and more optically active oils than the first crop} stem oils are lighter and optically rarer than leaf and flower oils. The refractive index, density, and optical rotation of the oil increases gradually with the age of the plant. She physical constants of the oils distilled from the plants growing at lower altitudes show higier values (tables III. 3 and III.4) than the oils obtained from the plants growing at hi#er altitudes, the oils obtained from the matured plants preferably from the fertile soils are more soluble than the oils obtained from the younger plants.The stem oils show lower solubility than leaf and flower oils.

The acid number of the oil shows a peculiar trend as the plant grows to the age of three months (Fig. III.3). In the leaf and flower oil it decreases regularly

ESTER

NU

MB

ER

F IG .m .2 . VARIATIONS ESTER NUMBER

(THYM U S SERPYLLUM L.3

ACID

V

AL

UE

3-65 LEGEND'- AS SHOWN IN FIG.m.l.

3*60

3-55

3-50

3-45

t 3*40

3-35

3-30

3*25

3 20

3 1 5

it

/ ✓

3.-K)'---fe-MARCH APRIL MAY JUNE SEPT. OCT NOV. DEC.

FIG. m.3 VARIATIONS IN ACID VALUE OF THYME OIL.

ia the stem oils it shows a regular increase.The decrease and the increase in acid number takes place more rapidly at fertile soils, particularly at lower altitudes, than at acidic low mineral containing soils. JULke physical properties the acid number of the oil is subtly hi#er during the second crop than daring the first crop. The ester number and the totalphenolic content of the oil (Figs. Ill.2 and III.4)increases considerably in the plants up to the age of three months, whereafter there is no appreciable increase in their contents. The formation of esters and phenols seems to be favoured at basic vaineral-rich soilsf their percentages are also hitter during thesecond crop than during the first crop, stems containphenol-poor oils.

Easuusas. 4a S&g&ksal fiftaaaittfltt

During the present study two alcohols— heptenolAnd terpinene»4-ol~-were also found present in the wildthyme oil. Their presence was confirmed by G.L.C.They were also separated by column chromatographyfollowed by fractional distillation, and were identifiedby the preparation of their derivatives. Terpinene-4-olwas identified as its nitrosyl chloride (ia.pt., 112°Cj

om.m.pt., 112 C) and heptenol was converted into methyl-amyl-ketone by oxidising it with chromic acid.The semicarbizone of methyl-aayl-ketone on recrystallisation

134

FIG m .4. VARIATION IN PHENOLIC CONTENT OFTHYME OIL.

395

from ethanol molted it 118.4°C. During columnchromatography heptenol was obtained with the early

o ofrictions of pet* ether (b*p*, 60 - 80 ) and was separated from it by distillation under reduced pressure* Terpinene-4-oi was isolated from the column by Stall ItgOs CHC13 ( 1£i 6i 1) * 4lthou$i the presence of these alcohols in small quantities is of little significance from the point of view of the flavour of the oil, yet it suggests their probable involvement in the ehloroplastidic reactions of the plant leading to the biogenesis of terpenoids* The detailed percentage compositions of sixty four samples of wild thyme oils are given in tables 111*5 and 111*6) table III*5 gives the percentage compositions of leaf and flower oils and table 111*6 gives the composition of stem oils*The variations in the percentages of lin a lo o l, geraniol, p-cymene, camphene, T -ter^inene, terplnene-4-ol, singiberene, and carvacrol are also illu strated in Figs* in *5 to 11X42*

Inter^ opulatiQn Cnaposltlojaal YagiafeLojm

The nature and characteristics of the substratum on which Thymus serpyllum L. grows has a marked influence on the composition of its essential oil* The plants growing at basic abd mineral-rich (fertile) soils (sites II and III), especially at higher altitudes, or where they are exposed to longer photoperiods, yield

3 0 1_______ I_.______ i------1---------- 1------- 1------- »-------1--MARCH APRIL MAY JUNE SEPT. OCT. NOV. DEC.

MONTHS-*

FIG.HL5 CARVACROL LEVELS VS AGE (THYMUS SERPYLLLU G E N D LINN)

LEAF AND FLOWER OIL STEM OILSITE I O------- ----- o ----------SITE n A------------ A ----------SITE IE D------ ----- Q-----------SITE IB ©------------ ©-----------

Soil malysis of Thymus serpylimn L. substratumT.LBLE I I I . l

property Site I Sit® II sit® III Sit© IV

Physical nature Silty- lojmy Silty- Loamy-loamy soil clay clay% moisture 6.9 17.7 11.36 10.47pH value 6.3 7.8 8.8 5.9Loss on ignition 9.613 7.011 6.510 4.952% nitrogen 0*236 0.325 0.379 0.198

*2% Ca 2.947 3.381 3.789 2.649

+2% Mg 0.731 0.994 1.046 0.648

4*1% 1C 0.357 2.214 0.416 0.216+1

% Na 0.879 0.706 0.432 0.449% carbon 2.76 2.28 2.68 3.63% organic matter 6.28 2.43 2.97 3.60% phosphorus 0.627 0.731 0.771 0.689C onductivity 0.49 0.62 0.80 0.30

X X X X-3 -3 *•3 -3IX) 10 10 10

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T.4BLB I I I .6Compositional Variation m the Leaf and flower oil (Thyraos serpyllum Ulan.}

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March I 43.00 3.76 1*06 1.00 0.76 1.60 1.83 3.10 2.84 7.28 15.00 6*83 2.3? 0.90 1.98 5.46 1.60II 44.06 4.20 1.96 1.48 0.20 0.80 1.89 3.30 3.34 7.84 1S.8B 3.42 2.47 0.98 2.99 4.38 1.00III 45.21 4.28 2*04 1*30 m 0.90 0.99 2.80 3*84 6.32 14.01 3*82 2.78 0. 70 3.40 3.01 1.00nr 41.60 3.36 1.20 0.83 0.40 3.30 1*68 3.60 3.01 8.38 M.60 4.83 3.417 1*16 3.08 4.27 0.92

April i 48. €0 4.25 1.46 1*28 0.20 0.99 1*60 3.60 2.74 8.08 12.00 4.20 3.10 1.J0 2.36 3.20 1.43ii 49.76 4.30 1*32 1*66 - 0*40 0.94 3.48 3*00 8.68 9.74 3.06 3.01 1.40 3*20 3.64 1.60

h i 47.90 4.72 2.62 1.25 - 0.38 0.98 2.98 3*20 7.96 11.00 3.29 3.61 1.62 3.70 2.52 1.10IV 44.40 3*13 1.26 0.97 0.30 3.00 1.32 3.90 3.24 7.40 11.92 3.20 3.66 1*07 4.02 3.98 1.30

May i 48.10 5.06 1*99 1*48 0.10 0.80 1.76 3.80 1.02 8.76 10.15 3.01 4.20 1.90 2.90 2.78 1.20ii 51.34 6.21 1.94 1.69 - 0.30 0.38 3.90 2.33 8.80 c.60 2.78 3.68 1*86 3.58 3*23 1*80i n 52.34 6.34 2.96 1*48 - 0.10 1.30 3.40 2*88 8.37 5.23 2.80 3.82 1.68 4.08 2.10 1*28i? 46.10 3.83 1*48 1*03 0.28 2.83 1.10 4.20 1.48 7.90 3.30 3.61 4.82 2.03 4.J3 3.88 2.00

June i 40.70 6.36 2.30 1.54 . 0.86 1*80 4.00 1.30 8.83 9.34 2.85 4.10 2.10 3.00 2.40 1.40ii 51.68 6,76 2.02 1.70 - 0.10 0.43 3.96 1.43 8.98 6.48 2.08 3.97 u r n 3.76 2.87 1.90m 62*96 6.93 3.33 1.97 - 0.16 1.30 3.46 1*73 8.94 4.23 2.01 4.08 1.74 4.18 1.98 1.40IT 46.60 4.13 1.82 1.23 • 2.81 0.97 4.48 1*28 8.32 4.88 3.99 5.90 2.30 4.98 3.40 2.10

tmiM

T~ "11 in W Z Z L IE J s n n E i T i r r

Sept. I 45.90 4.06 1.54 1.14 0.62 1.98 1.60 3.30I I 44.86 4.39 2.00 1.04 0.05 0.90 1.90 3.42

X II 45.73 4.48 2.38 1.39 - 0.30 0.94 2.97I? 44.50 3.55 1.38 0*92 0.35 3.50 1.60 3*o3

OCt. I 4 9 .5? 4.98 1.76 1.24 0.35 2.40 1*55 3.4611 30.34 4.9o l*o4 m 0.46 0.98 3.60

I I I 43.40 6.37 2.94 1*34 m 0.28 0 *99 3.10nr 45.47 4*56 urn 0.72 0.30 3*14 1.48 3.86

NOV. I 50*90 5.75 2.32 1.58 • 1.04 1.56 3.95I I 51.97 5.48 2.93 1.94 0.13 0.80 4.09

XII 62.92 ft. 86 3* 1 6 I*‘58 **• 0*20 1.10 3.53IV 47.90 4.91 1«77 1* 14 ** 2.97 1.36 4.24

Dec. i 51.16 6.03 2.94 l*o9 «» 0.49 1.40 4.06ii 52*46 5.94 3.44 2.07 #» 0.10 0.8? 4. 33

in 53.08 5.98 ii«40 2.01 «► 0.21 1*30 4.03X¥ 43.36 5.34 2.03 1*43 * 2*69 0.79 4. 62

204

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2.75 6.84 13.43 4.90 2.93 0.99 0.97 4*94 1.003.62 5.91 15.01 3*68 2.68 1.04 3.14 4.31 1.203*00 5.93 13.39 3.78 2.32 0.92 3.54 3*21 1*023.33 6.63 10.61 5.03 3.17 1.35 4.20 3.92 1.10

1.94 7.30 6.50 4*30 3.46 1*42 1*88 3.70 i*ao3.31 6*04 9.07 2.95 3.32 1.3? 3.42 3.44 1.403.21 3.43 8.94 3.05 3.64 1.66 3.94 2.41 1.403.39 7.56 9.07 4.31 3*66 1*39 4.37 3.39 1.30

2.87 7.96 7.23 4.40 2.63 1.64 1.43 2*16 1.702.31 6.23 6.21 2.30 3.53 1.76 3.78 3.03 1.702.41 3.50 3.31 2.43 3.34 1.79 4.27 1.99 1*502.08 3.02 5.00 3.16 4.12 2.62 4.99 3.16 1.50

1.60 8.33 8.26 4.93 1.20 1.93 1.20 1.99 2.001.62 6.65 6.00 1.88 3.94 1.70 3*85 2.50 1.302*08 9.01 1*94 2*08 3.95 1.94 4.23 1.82 1.902.50 8.20 3.25 2.32 4.29 2*88 5.03 2.3? 1.60

Compositional Variation la tae stea Oils of Tfoyaais g»t«i laa lAaa.

? m w iii*6

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1........ f f "I’f i W ~ ""~f I f : r '""TO T T f i i i IX Z j L I I I M Z ” i r ~ & I3 T ~IriP 1? I f f I7 iT ~ " I f i i f

March I 31.82 0*65 0.54 o.ao 1.02 5.60 1.06 3.88 3.90 20.31 17.31 9.09 3*56 1.77 3.00 4.00

11 32*01 0*70 0.60 0.20 1.00 4.90 1.32 3.48 3.30 3.40 18.55 3*90 3.94 1.07 4.30 4.60111 32.21 0.85 0.64 0.34 0.72 4.80 1.45 4.01 2.90 3.00 27.S2 3.96 3. IS 1.50 4.67 5.21

I? 31*00 0*30 0.51 0.21 1.49 6.20 0.98 3.61 4.23 10*90 17.07 3.01 3.46 1.10 5.<s2 3.32

April 1 33.85 0*96 0.63 0.30 1.06 5.20 1.24 4.26 3.95 12*11 16.50 9 .39 3.81 2.60 3.10 3.35

II 34*60 1.46 0.78 0.54 1.08 3.00 1.44 4.46 3.35 9.33 27.75 9.30 3*05 2.40 3.70 o.95III 34.66 0.90 0.69 0.36 0.78 4.91 1.49 4.29 2.99 8.12 2J5.66 9.50 3.40 1.64 3.91 5.00

If 32*46 0.94 0.81 0.65 1.14 6.77 1*03 3.76 4.78 11.1C 12*62 8.56 3*71 1.32 5.91 3.40

VLxy I 34*70 1*33 0.31 0.45 1.08 4U90 1.68 4.98 4.08 13.02 12.03 9.99 3.94 2.80 3.40 2.94II 36.00 2.38 0 .9a 0.80 1*20 2.30 1.60 3.50 3.40 9.30 16*25 3.35 £.15 2.50 3.46 3.54

III 35*66 0.99 0.74 0.39 0.82 4.97 1.56 4.35 3.09 8.27 14.14 9.68 3.62 !ȣ&> 3.52 4.58

I? 32*97 1.27 0.99 0.99 1.20 6.91 1.21 3.19 4.86 11.31 20.36 8.62 Qa«oo 1.41 4.84 3.56

M m I 35.50 1.99 0.83 0.50 1.23 4.04 1.68 5.30 4.30 13.12 9.01 20.20 4.19 3.15 3.20 2.82

II 35*70 2.30 0.95 0.90 1.26 2.00 1.78 3.10 3.52 8.45 11.07 9.55 3.04 2.63 3.08 3.54

III 36.40 1.04 0.80 0*39 0.60 5*20 1.77 4.42 3.19 8.46 13.33 9.72 3.77 1.98 *.90 4.01

IV 33*40 1.20 1.26 1.00 1.10 7.32 1.62 3.92 4.94 11.40 8.25 8.76 3.91 1.58 4.76 3.69

205

T*BX*£ I I I .6 (CoQtd.)

«JL— . ■JOL. ....T ' V I VII J O £ L IX - -Jet__ jffiL. i in .."xvi W Iffff^ M H W M W I

Sept. I 32. 2G 0.85 0.99 0*26 0.96 6*50 1.70 3.99 3.95 10.07 36.02 9.39 3*58 1.34 3.40 3.90II 32.80 0.85 0*64 0*60 0.96 4.20 1.40 2.80 Kl OO 9.32 £7.45 9.35 3*20 1.97 4.40 3.9III 33*94 0.96 0*65 0.35 0.70 4.86 1.52 4*26 2.87 Si OO O * *£«# 1&* 0& 8.65 3.40 1.53 4.70 5.31If 31*41 0*93 0*® 0*32 1.21 6.40 1.20 3.61 4.41 10.37 14.36 3.30 3.50 1.33 5.86 3.40

Oct. I 34*4? 1*20 0.7C 0.36 1.04 5.00 1.30 4.75 4.16 30.87 10.96 30*14 3.92 2.78 3.50 3.23II 35.24 1*60 0.80 0*19 1.06 2.90 1 .2 0 3 .29 3.41 9.20 16. W 9.63 3.00 2.50 3.67 4.50

III 34*73 1.15 0*79 0*35 0.68 4.98 1.56 4.36 2.96 3.30 16.31 3*94 3.70 1.72 3.64 4.99IV 32.67 0.99 0*89 0.71 1.67 6.88 1.62 3.32 4.36 11*36 8.66 8.69 3.77 1.39 5.34 3.63

Nov. I 36.80 1.®? 0*91 0.51 1.06 4.ao 1.40 5.46 4.23 H.86 9.33 10.52 4.09 2.95 3.70 2.54II 36. @0 2*44 1*01 0*95 1.20 2.40 1.63 3.03 3.46 9.90 16.00 9.31 3.45 2.65 3.50 3.83

III 35.96 1.23 0*36 0.38 0.74 5.30 1.79 4 .4 5 3.00 14. i9 9.21 3.85 1*95 2.86 4.32IV 33.04 1.22 1*19 1*07 1*78 7.3JS 1.72 3.91 4.39 11.06 7.98 8.72 3.94 1.51 4.72 3.79

Dec. I 33*40 2*43 0*99 0.79 1.22 3*20 1.68 5 .9 0 4.60 11.84 5.78 20.70 4.34 3.35 3.90 2.16II 36.90 2.54 1.13 1.10 jl.30 2.30 1.30 2.86 3.67 3 0 .1 0 12.13 9.43 3.50 2.76 2.39 3.14III 36*86 i»m 0*91 0.40 0.50 5.40 1.S3 4*28 3.10 3.51 13.20 9.43 3.93 2.01 1.93 3.0©

IV 33*63 1*37 1*29 1.12 1.52 7*40 1.90 4.30 4.92 11. £7 5.68 8.95 4.06 1.73 4.62 3.99

206

20?

essential oils which are rich la phenols* The plants which thrive at acidic , low-mineral , and nitrogen- containing (less fertile) soils (sites x and IV) contain oils which are rich in non*phenolic terpenoids and alcohols

The inter-population variations in the constituents of the wild thyme oil, obtained from the plants of the same age group, are not uniform at various stages of the development of the plant. This is because their rate of change voiles from site to sitej such changes were found to be aaxtaum at the flowering stage* the variations in the composition of leaf and flower oils exceeds the

variations in the compositions of stem oils*

The percentages of phenollcs present in the oil, except iso-eugenol, increased with the increase in the alkalinity and mineral content of the substratum*However, in some cases, the oils obtained from the plants growing at mineral-deficient soils were found to contain slightly higher percentages of phenols than the oils distilled from the plants thriving at fertile soils•This could be probably due to abnormal climatic changes at these sites. During the second crop, the percentage of phenols was found to increase with the Increase in the fertility of the soil, at all stages of plant development* Maximum variations were observed in the percentages of earvacrol and thymol$ they showed almost similar mean standard deviations, althou<£i their percentage in a

PERC

ENT

ZIN

GIB

EREN

E

t

13-80

13-00

12-20

11-40

10-60

9-80

9-00

8*20

7*40

6*60

5-80

LEGEND:AS SHOWN IN FIG.ffl.5

O '‘tX.

/

6

s '

p ~c.Q-~

/ / ✓✓✓s**

A "---'A

JD'

----

A '

MARCH APRIL MAY JUNE SEPT. OCT. MONTHS —

NOV. DEC,

FIG.B.6 PERCENT VARIATION ZINGIBERENE VS AGE.(THYMUS SERPYLLUM LINN)

308

particular oil differed marginally. in l®*f and flower oils» these phenols increased with, the increase in the mineral content of the soil, at all stages of plant development. But the order of sites in %tolch their percentages increased in stem oils was not the same at various stages of the #?owth of the plant. In stem oils the percentages of thymol and iso-eugenol Increased in one order of sites while the percentages of oarvacrol and eugenol increased in the other order of sites. Less-fertile soils seem to promote the formation of thymol in stem oils. These oils shoved greater inter-population variations at sites XI and XIX man at sites X and XV. The inter-population variations in the phenolic constituents of the oil were mueh higher at maturation stage of the plant than at the earlier stages of the growth of the plant.

With the Increase in the mineral content of the soil, the percentage of heptenol and terpinene-4-ol decreased in all parts of the plant| a small decrease in the percentage of geraniol and 1- OC-pinene was observed in leaf and flower oils also* However, at various stages of the development of the plint, the variations in the percentage of geraniol and 1-OC-plnene in stem oils did not show any definite relationship with the composition of the soils, on the whole, the percentage of geraniol in these oils was found hi#ier at

PE

RC

EN

TA

GE

T

ER

PE

NE

NO

L

L e g e n d - . a s s h o w n in f i g . in.5

FIG . IH,7. PERCENTAGE TERPINENE -4- 01* VS.AGE.(THYMUS SERPYLLUM LINN)

sites XX and XXX than at sites I and XV and that ofi- oc«pinene was found more at sites I and XV than at sites XX and XXX* The percentage of linalool, aingiberene, and T«*terpinene iacreased in the oil with the increase in the percentage mineral content of the soil, but the soils containing hi#ier mineral content than the soil of site XX did not seem to favour their formation in the plant* The psrcentage of T'-terpinene, however, was found to be lesser in the oils obtained from the plants growing at fertile soils than the oils distilled from the plants growing at less-fertile soils*In leaf and flower oils, the percentage of linalyl acetate increased, but its percentage decreased in stem oils with the increase in the mineral content of the soil*On the average, the percentages of camphene, p-cymene, and limonene were lower at sites XI and XIX than at other sites* Their percentages varied in different manner at different stages of plant development* The inter­population compositional variations in stem oils were found different from the variations in leaf and flower oils*

Depending on the substratum and age of the plant, the oils from various parts of the plant bore significant qualitative and quantitative compositional differences*Hie oils distilled from leaves were qualitatively similar

309

PE

RC

EN

TA

GE

Y

TE

RP

IN

EN

E

MONTHS—

FIG.IIL8 PERCENTAGE Y-TERPINENE VS AGE (THYMUS SERPYLLUM LINN)

210

to the oils distilled from flowers and their percentage compositions varied by not more than ♦ 0*01%. For this reason their percentage compositions have been tabulated under one head (table III,5). The difference in the percentage of various compounds was mostly observed in the non-phenolic part of the oils} leaf oils bore slightly hi^ier percentage of terpenoid hydrocarbons and alcohols than the flower oils*

Stem oils, on the other hand, differed from leaf and flower oils, both qualitatively and quantitatively\ stem oils did not contain dkborneol , and bore comparatively much lower percentages of phenols than leaf and flower oils* The difference in the percentage of phenols is compensated by the presence of some non-phenolic oxygenated and hydrocarbon terpenoids, and heptenol (tables III.5 and III.6) in the oil. Leaf and flower oilscontain lower percentage of zingiberene, caj%h®ne,p-cymene, and T -terpinene and their percentage variations overwel^& the variations in the percentage of minorphenols. The variations in the content of 7°"‘terpineneand zingiberene are very prominent. Depending on the age of the plant, other hydrocarbons, such as limonene, p-cymene, and pinenes show much lower variations than ses(juiterp@n0lds and terpinene. 1- f3 -plnene varied by hi^ier percentages than 1- CC-pinene. The percentages of pinenes, heptenol, geraniol, and terpinene-4-ol were found to be more in stem oils than in leaf and flower oils.

211

r.arnnn»n-.innal vaclatlong with Jta BCTttaHMUt s£ S hi E liO t-

&t every stage of the development of the plant* the percentage of some constituent* in its essential oil increased while that of others decreased* these changes in the composition seen to he governed by the nature of the substratum and the climatic conditions prevailing at a particular site* Major changes in the composition of the oil v«re observed at the Hovering stage of the plant*

a s the plant grev to maturity, the percentage of phenolics in the oil increased gradually in ail its parts. The percentage of carvacrol and thymol increased by larger amounts than the percentage of eugenol and iso-eugenol* The increase in the percentage of phenols vas more in leaf and flower oils than in stem oils, especially at mineral«*rich soils. She percentage of thymol and eugenol Increased in greater amounts at site II than at site III. During the first crop, the percentage of eugenol in leaf and flover oils shoved a sii^it decrease at site XI, up to the flowering stage • but a small decrease in its content vas observed at sites III and I? during the second crop, She variations in the percentage of iso*eugenol in leaf and flover oils vere insignificant during the first crop} but during the second crop, its content in stem oils shoved a higher increase than in leaf and flover oils.

PE

RC

EN

TA

GE

C

AM

PH

EN

E

LEGEND: AS SHOWN IN FIG.m.5

MONTHS —

FIG.III.9 PERCENTAGE CAMPHENE VS AGE.(THYMUS SERPYLLUM LINN)

The percentage of geraniol also increased in the oils at every stage of plant development* During the first crop, its formation in leaf oils vas facilitated at mineral* deficient soils, but daring the second crop it vas favoured at mineral-rich soils, m e percentage of geraniol in stem oils decreased after the Hovering of the plant at site XI* as against this, terplnene*4»ol decreased in leaf and flower oils at a U sites, but increased ia stem oils at sites XIX and IV| its percentage in these oils increased at sites I and II* in increase of about Q*5% in the percentage of terplnene-4-ol was also observed in leaf and Clover oils at site I during the early stages of the grovth of the plant* The amount of linalool, llnalyl acetate, monoterpenoids, and sea quit erpenoids showed a considerable variation with the development of the plant* During the first crop the percentage of linalyl acetate decreased continuously in leaf and flower oils, at sites m and IV* at sites I and It, however, its percentage in these oils increased during the early periods of the growth of the plant* on the other hand, in stem oils, the content of linalyl acetate Increased gradually at various stages of the development of the plant at all sites* The variations in the percentage of linalool were found to be totally different from the variations in the percentage of geraniol, in various parts of the plant* The percentage of heptenol

218

LEGEND: AS SHOWN IN FIG. m

MONTHS-*

FIG.IH. 10. PERCENTAGE CYMENE VS AGE.CTHYMUS SERPYLLUM LINN)

decreased In leaf and flower oils but increased in small amounts in stem oils*

The singiberene content in the oil increased gradually with the age of the plant; the increase in its content was less favoured at mineral-rich, soils than at acidic and low-mineral soils* in stem oil a slight decrease in its percentage occured at the flowering stage of the plant* The percentages of T-terpinene, pinene, and limonene were found to decrease with the growth of the plant* However, a small increase in the percentage of 1- 0£*pinene was found to occur in stem oils at the early stages of the development of the plant* During the first crop the camphene content in leaf and flower oils decreased, except at site I, where its percentage increased at flowering and post-flowering stage* Against this, the percentage of camphene in leaf and flower oils increased up to flowering stage, during the second crop, and then started decreasing till the maturation of the plant* In stem oils, its percentage increased gradually at all stages of the growth of the plant*

From the foregoing discussion, it is clear that ecological condition* have a marked influence on the crop yield of the plant and its oil content and the physical and chemical composition of these oils*The chemical composition of the oil undergoes a marked

213

PE

RC

EN

TA

GE

G

ER

AN

IO

L

LEGEND: AS SHOWN IN FIG.IH.5

MONTHS-*-

FIG.HU! PERCENTAGE GERANIOL VS AGE.CTHYMUS SERPYLLUM L IN N )

PER

CEN

TA

GE

LIN

AL

OO

L

LEGEND*. AS SHOWN IN FIG.U1.5

MARCH APRIL MAY JUNE SEPT. OCT. NOV. DEC.

MONTHS-*"

FIG.HT. 12. PERCENTAGE LINALOOL VS AGE.CTHYMUS SERPYLLUM LINN)

change during the development of the plant} major changes take place between the commencement of the flowering and the formation of the seeds, the essential oils of leaves and flowers are almost similar, but they differ from title stem oils both qualitatively as well as quantitatively} stem oils do not contain d-borneol.The variations in the percentages of iso-eugenol and some oxygenated and hydrocarbon terpenoids occur both with the change in substrata as well as the development of the plant. There is a gradual increase in the percentage of all the four phenols, zin^Lberenet T-terpinene, p-cymene, and camphene as the plant develops to maturity. The increase in the content of these compounds is non-linear and deviations in stem oils and leaf cxLls fall in different ranges, except in the case of some phenolics. in stem oils, the variations in some constituents are different from the variations in leaf oils, particularly in geraaiol and linalool content. These facts account for the controversial results reported about the chemical composition of wild thyme oils from different places. They also suggest that the plant aight be following two different biogenetic paths leading to the development of phenolic terpenoids in leaf and flower and stem oils. Since a&neral-rich fertile soils with low moisture content favour the production of higher crop yields and better quality of the essential oil, the plant may be

214

cultivated at well-drained soils to which, adequate amounts of N.P.K# fertiliser mixtures have been added} the p^ of the soil should be maintained between 8*00 and 9*2.The plants can be safely harvested during July and December for the production of ethereal oil and its constituents.

315

i i i . a . i i as, & a u a&

Tazetus mi nut a Lion.

In Kashmir Taaetus mlnuta L, can be harvested once a year (November— December) • The nature and the composition of the substratum Influences not only the growth of the plant, but also Its oil content and the composition of its volatile oil. The characteristics of the soils on vtoich the plant was raised are given in table III.7. site l bore acidic soil with low mineral content and hi^i percentage of chloridef, sulphates, and nitrates, and sites n and III contained lower percentages of these compounds than site I and were rich in carbonates and mineral contents, lio significant difference W4,s found in the flowering time of the plant at various sites but flowering was dense at basic and mineral-rich soils. The growth of the plant was also affected by the nature of the soils} the plants raised on acidic soils were generally dwarfish and did not grow beyond 40 to 136 cms., while at alkaline and fertile soils the plants were about 5.S to 6 ft. tall (table III.8),

The percentage yield and physicochemical properties of three oils, obtained from flower heads (on maturation of seeds) of the plants raised at three different soils are given in table III.9. The yield percentage, density, refractive indices, optical rotation, and total carbonyls of the oils increased with the increase in the mineral

237

Soil i&alysis of the substratum of T^etua mimta Linn*table III.?

Bite 1 site iiSoil texture Sandy* silty- loamy

loamy loamypercentage moisture 3*4 6.9 9*30P^ of the soil 4*2 5*4 9*3Loss on ignition 6*510 6.372 9*613percentage of nitrogen 0.379 0*542 0*614percentage of calcium 3*4*1? 3*218 2*643percentage of magnesium 0*714 0*638 0*912percentage of pottaslum 0*644 0*737 0*843percentage of sodium 0.479 0.684 0*322percentage of phosphorus 0.232 0*629 0*714percentage of carbon 2*14 2*43 3*193percentage of org. matter 4.4?7 4*02 6*243percentage of carbonate 3.90 4*0 o.32percentage of sulphate 2*43 1*37 0*66percentage of chloride 3.11 1*32 0.36percentage of nitrate 1.3d 2*96 2*63Conductivity 0.5 X 0*6 X 0*9 x*3 *3 *3ID 10 10

TABLE III.8 phenol© gical Data on Tagetut aiauta Linn*

238

alt# X _ Site IX site IIIDate of cultivation

March, 20 March, 28 April, 23

Date of flowering Oct.) 6 Oct., 4 Sept., 23average heigit of the plant on flowering

36 cms. 120 cats. 158 cats.

Date of seed formation

Nov., 25 Nov., 13 Nov. , 20

Height of t&e plant on harvesting

40 cos. 128 cas. 133 cms.

table ixx.9Phyiicochs-Jieal Characteristics of tke oils of Taaetasainata Lia*i.

Observation Site X Site II Site III

¥ield percent Q.9S 1.33iief. index at 20°C 1.4334 1.4957 1.4932Op. rot. at 20°C o / + o , 24 + 6°, 13 0 / + 6 , 3Density at 20°C 0.8713 0.8703 0.8722Total carbonyls CNH^H methovi) 34.1% 30.09% 4 7 .4 m

Ac id vaiut© 0.41 0 .59 0.27ister value 38.47 30.23 27.81Sol. in 90% ale. (in vols.) 1 - 1.8 1 0.7 - 0.9

219

Compositional Variations in the Oil of Tarsus miouta L.h i .9

C0IQ£>0ttndPercentage.

Site X Site II Site III

Tag®tone 10*20 14*33 18*27Limonene 2*90 1*25 0*94Ociaene 11.30 13*34 15*02L Inal col 3*40 1.17 0.601-carvone 8.20 5.97 3*98DC »pinene 0.93 1*03 1*38Caaphene 2*40 1*29 0*373 -phellandrene 6.46 3*89 3*00Geraniol. 4.30 3,83 2*45Phenyl ethyl alcohol 12*53 12.73 13.65Linalyl acetate 2.47 2.07 3*00Eudesiool 4*46 4.27 3*86Oeranyl acetate m 1.94 0*88iroaadendreae 12.30 14.82 16*62pulefoone 4.08 3,85 3*60Tagetenones 6*80 5.97 5*07Salicyl aldehyde 4*34 4.21 3*52

content of the soil, on the other hand their acid number, ester number, and solubility decreased gradually from site I to site III. Qualitatively these oils were similar, but they showed significant quantitative compositional variations. The oils obtained fro®, the plants grown at acidic soils contained lover amounts of tagetone, oclmene, ^-pinene, phenyl ethyl alcohol, and aromadenarene than at fertile soils\ their percental* increased from site I to site III. Very small difference was observed in the percentages of esters, eudesaol, and pulegoae.

From these observations it is clear that Tagetus rainuta Linn, can thrive better at basic joineral- rich soils and the quality of its essential oils will be excellent at these soils.

2 2 1

I I I .3*111 sttfQaai YjjrlAtiQja in th& c^miogitiQn of the

M 1 of mtmlft 1 ^ * 0 ^ s & z.

The leaves of an ^ liureol* can be collected

daring iprii and December for the production of its

essential oil* The physicochemical properties of the oils distilled from the plants collected during the

months of tpril, July, October, and December are given

in table III. 11* The properties and composition of the

oil obtained from the leaves harvested durinj the

month of June are given in chapter II (p.447).

The plant oil shows considerable variations in the

physicochemical properties during the three seasons*

The yield of the oil and its density, refractive index,

optical rotation, and ester value increases gradually

from spring to autumn. Hie oil obtained froti September

harvest contains the hipest percentage of esters

(Unalyl acetate). There is a significant seasonal

variation in the quantitative composition of the oil,

althou^i the oils obtained during the months of June and

September do not show much difference in their composition*

During the three seasons the percentage of linalyl acetate,

llnalool, ^ -cltral, ber^aptsne, and methyl heptenone

Increases while the percentages of terpen© hydrocarbons

iad geraniol decreise from April to September; the

variations are maxiraum between iprll and June.

2 2 2

TlBLB 111,30 physicochemical properties of the Oils of laureola sells and zucc.

property April June September

0.831.4606- 4®. 36 - 4'

Yield percentRef. index at 20°COp# rot* at 20°cDensity at 20®C 0*8899aster value 32*0%(as linalyl acetate)Total alcohols 16.3%(ealcd* as linalool)Sol* (in voluaes of 1*6-230% alcohol)

1*99 1* 461/S

360*8906

66* 31$

29*46%

a-2.3

2. 20

1.4737 - 4*, 62^ 0*8963

71*01%

28*06%

2-3

223

TiBLE III. 11Compositional Viriatiosa in the Oil of ski mala lmrtoli

confound April June September

XAualyl acetate 40.0% 4^.92 44.43Linalool ao*bH £3.70 24*32(DC •pineoe 4.fc0 3.81 3.71jS* -phellandrene 3.60 2.10 2.06(X -terpiaeol 6.32 4.00 3.95OeTiiniol 3.49 1.20 1.17Linonene 3.04 0.00 0.69|3 -citral 0.99 1.60 1*73Cadiaene 0.21 0.43 0.61Bergaptene 2.36 4.00 4*07Methyl hepteaone 4.00 5.01 5*30

Hote* and References

I. Sievers and Lawman, U.S. Dept, amt. Tech. Bull (1933), 378.

2* Charabot, E.and hit coworkers have published a series of papers on cliaatoiogical influence on essentialoil production and their chemical composition.4 brief account of their observations has been given by auenther, I., The Ess, oil* 0950)1* 69-74.

3. Berry, et.al, £. Cheat. Soc. (1937), 1443.4. Malinger, T.M., £&*£. thesis (Univ. of ®onlngen)

(2966).5. Maarse, H. and £epn«r, K.E., Jys£ic. and Food Chem.

(1970) 2 & (0), 1095*1101.6. Maarse, H., glavour Ind. (1974) £, 278-281,7. 4»es, Q.B., et.al, Tropical Science (1 9 6 9 ) VL (3),

170-73.8. Wickramansini&e. iUL.. Phytochsa. (1974) j£, ao57*63.9. Hefendehl, F.W. and Murray, M.J., -ibid. (1972) ii, 189$ 2469.10. Zavarin, S. and Snajberk, £,, Pure and abb. Cheat.. (1973) j&, 411.II. Zavarin, 1. and Snajberfc, K,, Pkartoefoem. (1972) 11.

1407.IS. Razdin, T.K. and Koul, G.L., Perfum (1974) 18

(Pt. a), 9*17.13. Jackson, M.L., soil analysis (Asia Publ, HousetBombay) (1962).