E. T. Contis et al.

(Editors)
Food Flavors: Formation, Analysis and Packaging Influences
1998 Elsevier Science B.V. All rights reserved

443

EGYPTIAN ONION OIL

Nadim A. Shaath and Frederick B. Flores
Kato/Nickstadt-Moeller, 1169 Edge water Ave., Ridgefield, NJ 07657
ABSTRACT
The common onion (AlUum cepa) belonging to the Lily family, is among the
oldest known cultivated plants, and was cultivated in Egypt, China and India
before the beginning of recorded history. Onion contains a volatile oil, fixed oil,
protein, cellulose, sugars and minerals. The volatile oil content of onion depends
on the variety of onion used and the distillation processes employed. The average
yield is 0.015 percent oil. The chief constituents of the oil are di-n-propyl
disulfide and dimethyl-n-propyl disulfide. Generally, one pound of the oil has the
flavoring strength of 5,000 pounds of fresh onions or about 500 pounds of
dehydrated onions.
This steam distilled oil contains numerous volatile
components, mostly alkyl and allyl di- and tri-sulfides. We identified 32 of these
chemicals using dual capillary column Gas Chromatography in combination with
Gas Chromatography/Mass Spectrometry. The commercial significance of the oil
and its full chemical analysis is discussed.

INTRODUCTION
Onions^ are believed to be native to Southwestern Asia. They are known to
be among the oldest known cultivated plants. Egyptian priests placed onions and
garlic as offerings on the altars of their Gods. Onion has an ancient reputation as
a curative agent, highly valued by the schools of Galen and Hippocrates. It is
high in vitamins A, B and C and shares many of the properties of garlic, to which
it is closely related. Raw onion helps to keep colds and infections at bay,
promotes strong bones and a good blood supply to all the tissues. It acts as an
effective blood cleanser which, along with the sulfur it contains, helps to keep the
skin clear and in good condition.
It has a sound reputation for correcting
glandular imbalance and weight problems [1].
The common onion, an herbaceous biennial plant, has a single large bulb
from which arise one or more leafless stalks that may grow to about 2 2 feet to 6
^ Onions (Allium cepa in Latin) are: Basal (Arabic), Yang Tsung (Chinese), Ui (Dutch), Sibuyas
(Filipino), Oignon (French), Kremethi (Greek), Cipolla (Itallian), Luk (Russian) and Cebolla (Spanish).

444

feet high (depending on the variety and growing conditions), with a terminal
cluster of many small greenish-white flowers. These are characterized by their
penetrating pungent and long-lasting aroma, remarkably characteristic of fresh
onions. Although the onion is hardy and may be grown under a wide range of
conditions, it is a temperate climate crop and prefers relatively cool, moist soil
rich in organic matter but moderately low in soil acidity. The onion may be
grown from its small black seed, from small bulbs called "sets", or from
transplants; commercially, most onions are grown from seed. The bulb itself is
used as a vegetable or as a seasoning, and the green parts of the plant may be
mixed in a fresh salad.
The seed is planted in rows 12 to 16 inches apart or less, depending on
conditions. In well-cultivated land, with effective weeding, herbicidal control,
adequate irrigation, and fertilizer application, yields of 4 to 12 tons or more of
fresh onion bulbs per acre may be obtained, depending on the weather, the
fertility of the soil, and the variety of onion.
In the United States,
storage and spring/summer.
outer skin and a firm inside.
color skin and is more fragile

onions are basically divided into two categories -The Storage Onion has a thicker, darker, paper-like
The spring/summer onion has a thinner and lighter
than the storage onion.

The Storage Onion is more pungent than the spring/summer onion because it
has a lower water and sugar content. They also do not bruise as easily. Their
season begins in August and goes through March. Typical storage onions are
available in red, yellow and white varieties.
Spring/Summer Onions are sweeter and milder than storage onions and are
sometimes called, "designer onions". Their season begins in April and ends in
August. Many of the varieties are well-known to onion lovers: Texas Sweet,
Sweet Imperials, Carzalia, Maui, Vidalias, and Walla-Walla being chief among
them.
Turkey is among the largest onion producing countries in the world, and
ranks third largest in production of all vegetables after tomatoes and potatoes.
Onions in Turkey are classified as follows:
Short and Medium-Day Onions are usually white skinned, have high crop
yield, high water content and a relatively sweet taste. They are non-storage
onions and have a low solid content (5% - 8%). These onions are good for fresh
consumption only.
Long-Day Onions are usually domestic varieties, have purple/violet inner
skins, high solid content (8% -11%) and are stronger in taste. Under suitable
conditions they can be stored throughout the year.

445

There is no remarkable relationship between the onion type and

cultivating regions. There are nine major cultivation regions in Turkey with
different climatic conditions. Within these regions both storage and non-storage
onions are grown.
In Egypt, terminology such as short, medium and long-day onions does not
exist. Its equivalent is:
Winter crop where production holds for 4 months during November,
December, January and February. At that time, the crop is whiter in color,
contains a higher percentage of water and, consequently, onions collected during
that period are sold for dehydration or fresh consumption.
Summer crop (long-day onions) can, as the name implies be stored for a long
time. Long-day onions can be shipped fresh to Europe and are the onions that
are produced from the second half of April through June/July.
Some of the "giant producing" areas of the world are the Peoples Republic
of China - 3, 980, India - 3, 400, the former U.S.S.R. - 2, 200, U.S.A. - 2, 200, and
Turkey - 1, 600. (All quantities expressed in thousand of tons.) It should be noted
that the Egyptian, Dutch and Italian production of onions are about the same
levels of 500 thousand tons each.

ONION OIL
Onion oil is obtained through the distillation of crushed fresh onions which
have been allowed to stand for a few hours before distillation. As onion
constituents are partially water-soluble, a special recovery technique is necessary
to achieve a high quality oil in a yield of about 0.01 to 0.03 percent, depending on
the type of onion, ripeness of the bulb, and season.
Onion contains a volatile oil, fixed oil, protein, cellulose, sugars, minerals,
etc. The volatile oil content of onion depends on the variety of onion used and the
distillation processes employed. The extractives are, to some extent, watersoluble. The average yield is 0.015 percent oil which has a tendency to crystallize
upon standing. The chief constituents of the oil are di-n-propyl disulfide and
methyl-n-propyl disulfide. Generally, 453.5 g (1 lb) has the flavoring strength of
two tons of fresh onions or about 227 kg (500 lb) of dehydrated onions. Basic
research is continuously being conducted for:
i.
ii.
iii.

yield improvement;
reducing the relative GC ratio compounds at the head and tail ends;
increasing relative GC ratio compounds of the middle section or
"body" of the oil.

446

Some of the main procedural parameters that directly influence oil production are:
Parameters

Influence

Maceration

extraction time
temperature

yield
quality

Distillation

extraction time
steam pressure
condensation temp

yield
equilibrium in GC
(head, body, tail end)

Whereas the dehydration industry uses onions with 18 to 22 percent solids,

onions used for distillation of onion oil requires low solids content. There is a
direct correlation between solids and oil content. Egyptian onions have a total
solid content of 8.0 to 9.3 percent depending on crop time.
Although the chemical composition of onion oil has been the subject of
numerous studies [2-5], until recently nobody had looked at the physiological
distribution of the characteristic flavor components. In 1975, Freeman reported
that there was a consistent flavor distribution throughout onion, garlic, and leek
[6]. This information should prove useful to the onion oil distiller as there is a
belief held by many distillers that there are localized portions of these alliaceous
plants which contain higher proportions of flavor compounds [7].
In another paper on onion oil, Galetto and Bednarczyk used the technique
of multiple regression analysis to correlate GC data with sensory evaluation data.
They found that there were six major compounds responsible for the aroma of
onion oil. Three of these compounds were methyl propyl disulfide, methyl propyl
trisulfide and di propyl trisulfide, while the other three were unknown [8].
Onion oil is used exclusively in flavors, rarely in fragrances, although such
application is very possible (violet, hyacinth, rose, etc. can benefit from minute
traces of onion oil for a distinct part of the top note). The oil has found an
increasing outlet in the canning industry in flavors for soups, meat, table sauces,
dressings, etc. There are wide limits for a suggested usage-level concentration,
according to the acidity and overall type of finished product in which the oil will
be incorporated [7].
The Food Chemical Codex [9] describes onion oil as follows: A volatile oil
obtained by steam distillation of the bulbs of allium cepa L. (Liliaceae Family). It
is a clear, amber yellow to amber orange liquid having a strong pungent odor and
taste characteristic of onion. It is soluble in most fixed oils, in mineral oil, and in
alcohol. It is insoluble in glycerin and in propylene glycol. Onion oil is purchased

447

mainly on the basis of its odor and flavor, which render definite specifications of
little value.
Identification. The infrared absorption spectrum of the sample exhibits a
characteristic pattern.
Heavy Metals (as Pb)
Refractive Index
Specific Gravity

Passes test.
Between 1.549 and 1.570 at 20^C
Between 1.050 and 1.135

Packaging and Storage. Store in full, tight, preferably glass or aluminum

containers in a cool place protected from light.
Functional Use in Foods. Flavoring agent.
The EOA [10] lists the following specifications for onion oil: An amberyellow to deep-amber oil; some samples may show a crystalline deposit; specific
gravity (25C) 1.0500 to 1.1350; refractive index (20C) 1.5495 to 1.5695. The
EOA specification points out that the sensory quality of this oil is of more
importance than physical characteristics.
Onion oil, garlic oil, leek oil and mustard oil all possess significant
concentration of sulfur compounds. Sulfides occur frequently in plants due to
glucoside degradations [11]. Twenty volatile sulfur-containing compounds were
identified. Onions have little smell until the tissues are cut or bruised. Once this
takes place the enzymatic reaction results in a complex mixture of sulfides that
can be recovered as oil of onion by distillation.

FLAVORING FORMS
Dehydrated Onion. The dehydration of onions to produce onion powder and
pieces of various sizes is a major activity in Egypt. The onions are first flame
peeled, washed to remove the burnt outer skin, and then mechanically sliced into
a perforated belt. The drying is carried out in a tunnel drier, the hot air
circulating through the holes in the conveyor belt. Onions enter the system with
a moisture content of about 80 percent and are dehydrated to about 4 percent.
The dehydrated product may be sold as such, kibbled to various mesh sizes, or
milled to a moderately fine powder [11].
Several methods have been proposed for the assessment of the flavoring
strength and pungency of both fresh and dehydrated onions. There is a good
correlation between the enzymatically produced pyruvic acid, odor strength and
pungency [12]. The relative flavor strength of fresh and dehydrated onion is
difficult to determine, as the two profiles are quite different. However, it is

448

generally accepted that onion powder is about ten times stronger than fresh onion
[11].
Toasted Dehydrated Onion. Onions contain reducing sugars whose quantity
depends on the variety and/or conditions of storage. These sugars may undergo
Maillard reaction during the latter stages of dehydration. High temperatures
result in a marked toasted note. There is a demand for toasted onion products
that have the odor and flavor associated with sauteed onions. These are available
in both powder and kibbled form in qualities ranging from lightly to heavily
toasted [11].
Onion Salt. This is a mixture of onion powder and salt, often with an
anticaking agent such as starch, tricalcium phosphate or silicon oxide, to
maintain dry free-flowing properties. Standardized dispersions of onion oil, with
or without onion extract, are available for use in blended seasonings [11].
Encapsulated Onion Flavors. Onion oil encapsulated by spray drying in gum
acacia or a modified starch is available as a flavoring ingredient. The strength of
these products depends on the manufacturer and may range from equal to ten
times stronger than onion powder [11].
Onion Juice/Extract (Oleoresin). Onion juice carries all of the available
flavor, actual and potential, and is a good basis for the preparation of a watermiscible onion flavoring. The juice is obtained by hydraulic pressing of the
washed onions [11].
Oil of Onion. This is obtained by the distillation of crushed fresh onions
that have been allowed to stand for some hours before distillation. As onion oil
constituents are partially water-soluble, a special recovery technique is necessary
to achieve a high-quality oil in a yield of about 0.01 to 0.03 percent, depending on
the type of onion and the season.

TECHNICAL DATA ON EGYPTIAN ONION OIL

The herbaceous plant of Onion is of extreme popularity throughout the
world as a vegetable and a spice used in many food preparations and as a
flavoring ingredient [13,14]. The plant contains a volatile oil which has been the
subject of abundant research. Studies of the chemical constituents of this oil have
dated back to as early as 1892 by Semmler when he noted the empirical formula
of the major component to be C6H12S2 [15]. In 1964, Sikher et al were the first to
use gas chromatography to quantitatively analyze onion oil [16]. Now we know
that the major components of this volatile oil are organic alkyl and allyl sulfides
of the empirical formulas of C6H14S2 and C6H12S2 [17]. Methyl propyl disulfide,
methyl propyl trisulfide, and dipropyl trisulfide are three of six chemicals

449
responsible for this characteristic odor [18].
Others who have studied the
chemical analysis of onion are Carson (1967), Schwimmer (1968, 1971), Galetto
and Hoffman (1976), and Albrand et al (1980) [6,12,18-24].

The physicochemical properties of the steam distilled Egyptian Onion oil are listed below:
Appearance
Odor
Refractive Index (@ 20C)
Specific Gravity (@ 25C)
Flash Point
Solubility

Yellow to amber clear liquid.

Strong pungent odor, characteristic of
fresh onion.
1.5300 - 1.5500
1.0310 - 1.1010
115F10F
Insoluble in water, propylene glycol,
glycerine; soluble in most fixed oils,
mineral oil and alcohol.

Several parameters directly influence the distilled oil product.

For
example, the time, temperature and agitation of the maceration process influence
the yield and quality of the essential oil. Time, steam pressure and condensation
temperature of the distillation process has direct bearing on the yield and balance
of volatile components in the oil. We have found that different geographical
locations within Egypt also have an effect on the product oil.
This steam distilled oil contains hundreds of volatile components mostly
alkyl and allyl di- and tri-sulfides. We identified thirty-two of these chemicals
using dual capillary column Gas Chromatography in combination with Gas
Chromatography/Mass Spectrometry. The instruments used for the identification
were the Perkin-Elmer Autosystem GC II and the Ion Trap Detector. The
capillary columns used were non-polar (Ultra 1) and polar (CBXS).

CHEMICAL ANALYSIS
Figure 1 shows a gas chromatogram of one region of Egyptian Onion Oil
run on a Ultra 1 column at 4C/minute. Thirty-two of the most prominent peaks
of onion are numbered and identified with their respective levels in all the data
reported.

450

Figure 1: Tj^ical GC profile of Egyptian Onion Oil

Table I is a summary sheet of the min/max levels found in three regions of

Egyptian production sites.
TABLE I: Summary m/n/max data of Egypf/an Onion production regions I, II, and III.

\REGION lA

REGION IB

REGION II

REGION II
THEORETICAL

CHEMICilNAME

MIN

MAX

AVERAGE

MIN

MAX

AVERAGE

MIN

MAX

0.31

1.75

AVERAGE

MIN

MAX

AVERAGE

AyERAGE

1.66

0.93

Allyltiiiol

0.13

0.72

0.32

0.13

0.23

0.62

0.82

0.92

2.52

Mffthylallyi(ulfid

0.02

0.09

0.03

0.01

0.02

0.02

0.00

0.34

0.08

0.02

0.12

0.07

0.06

Dimethyl Disulfide

0.06

0.59

0.22

0.02

0.03

0.09

0.04

0.35

0.20

0.12

0.55

0.26

0.23

Hexanol

0.02

0.24

0.15

0.03

0.17

0.11

0.01

0.12

0.08

0.02

0.10

0.06

0.10

trara-2-Hexanol

0.04

0.61

0.24

0.02

0.03

0.41

0.09

1.25

0.68

0.74

3.78

2.18

1.03

Meihyt ethyl disulfide

0.11

0.61

0.20

0.11

0.20

0.21

0.18

0.61

0.30

0.18

0.58

0.40

0.30

Allyl Propyl Sulfide

0.06

0.29

0.11

0.14

0.27

0.15

0.05

0.10

0.10

0.06

0.11

0.08

0.10

2,4-DimethylThJophene

0.04

0.11

0.07

0.06

0.09

0.10

0.08

0.34

0.14

0.15

0.29

0.20

0.14

3,4-DimethytThiophefw

0.42

0.72

0.52

0.31

0.45

0.55

0.62

2.46

0.95

0.91

1.88

1.24

0.90

10 cis-MethyM-Propenyi Disulfide

0.09

0.21

0.15

0.02

0.06

0.06

0.03

0.13

0.09

0.05

0.13

0.09

0.11

11 Methyl propyl disulfide

2.80

6.24

3.99

2.09

2.94

2.92

2.81

6.00

3.73

2.29

5.54

4.03

3.92

12 trans-Methyi-1-Propenyl Disulfide

0.77

1.41

1.09

0.27

0.57

0.55

0.98

1.70

1.24

1.21

3.94

2.41

1.58

13 Dimethyl Trisulfide

0.70

1.75

1.00

0.11

0.40

0.29

0.55

1.51

0.89

0.54

2.01

1.02

0.97

14 cis-Propyl Propenyl Disulfide

0.68

1.03

0.83

0.71

1.07

0.82

0.44

0.62

0.59

0.34

0.47

0.40

0.61

15 Nonanal

0.27

0.70

0.59

0.28

0.49

0.34

0.19

0.24

0.29

0.15

0.23

0.19

0.36

16 Dipropyl disulfide

13.89

20.92

17.46

33.03

41.64

33.34

15.65

34.33

21.15

10.13

21.10

15.58

18.07

5.86

5.01

4.94

7.94

5.30

4.50

6.78

5.49

5.11

17 trans-Propyl-Propenyl Disulfide

2.96

5.61

4.54

4.40

16 Methyl Propyl Trisulfide

7.05

6.60

7.83

3.48

6.75

5.00

8.04

13.37

7.87

5.68

9.21

6.85

7.52

19 cis-Methyl Propenyl TrisuHide

0.41

1.07

0.58

0.08

0.32

0.20

0.32

0.90

0.53

0.58

1.48

0.97

0.69

20 trans-Methyl Propenyl Trisulfide

0.44

1.00

0.66

0.10

0.35

0.24

0.00

0.99

0.61

0.75

1.63

1.21

0.83

21 Dimethyl TetrasuHide

0.26

0.50

0.33

0.00

0.18

0.14

0.27

0.47

0.35

0.32

0.67

0.49

0.39

22 Decanal

0.02

0.42

0.18

0.10

0.17

0.29

0.02

0.16

0.23

0.31

0.77

0.50

0.30

23 Methyl-1-(Methyl Thjo) Propyl Disulfide

0.06

0.29

0.17

0.04

0.06

0.09

0.04

0.56

0.28

0.53

1.60

0.99

0.48

24 Methyl Nonyl Ketone

0.21

0.40

0.35

0.49

3.18

2.60

0.35

0.54

0.86

0.23

0.49

0.43

0.77

0.58

0.12

0.39

0.32

0.57

28.19

15.31

11.97

13.99

13.79

13.37

0.55

25 cis-Propyl Propenyl Trisulfide

0.48

0.91

0.82

0.54

0.90

0.66

0.43

26 Dipropyl trisulfide

8.66

12.47

11.00

15.88

16.95

16.93

15.70

27 trans-Propyl Propenyl Trisulfide

0.17

2.58

1.25

1.09

3.24

2.88

1.09

7.67

3.02

5.13

5.44

5.38

3.22

28 Allyl propyl trisulfide

2.21

6.27

3.12

0.00

2.58

0.93

0.00

6.32

2.57

4.40

5.26

6.06

3.92

29

14.40

26.24

17.60

2.87

4.12

3.82

0.57

0.83

4.85

2.44

3.00

2.73

8.39

30 Methyl Undecyi Ketone

0.76

1.74

1.31

0.74

3.00

2.15

0.17

0.57

0.94

0.18

0.28

0.25

0.84

31 Dipropyl Tetrasulfide

0.62

1.35

1.12

1.10

1.24

1.22

0.33

1.22

0.96

0.94

1.70

1.34

1.14

32

4.82

6.14

5.67

1.81

3.06

2.11

0.42

0.65

1.83

0.35

0.97

0.70

2.73

2-n4<exyl-5-Methyl-2,3-Dihydrofuran^-one

2-n-Octyl-5-Methyl-2.3-Oihydrofura^3-one

451
A prominent percentage of dipropyl disulfide (DPDS) is found in onion oil.
The increase and decrease of this level is not due to any procedural variations,
however it varies because of the onion itself. The time of storage from the crop to
the distillation is directly proportional to the level of DPDS; the longer the
storage the greater the level.

98

100X

39

111

INT

182

\\\\ III, l,[ll

40

60

' I ' I ' ! ' I I ' I '

88

lee

120

148

I '

160

180

Figure 2: Mass Spectrum of 2-n-Hexyl-5-methyl-2,3-dihydrofuran-3-one

C6H14S2O2 MW=182

98

imt

111
INT

39

55

'"I""' ' ' I '

48
60

69

85

210
I ' I ' I ' { '

180
120
140
160
180
200
220
Figure 3: Mass Spectrum of 2-n-Octyl-5-methyl-2,3-dihydrofuran-3-one
C8H18S2O2 MW=210

The 3,4-dimethyl thiophene is believed to be formed from the

decomposition of methyl propenyl disulfide when exposed to heat and sun.
Methyl undecyl ketone is a degradation product of myristic acid. The 2-n-hexyl-5-

452

methyl-2,3-dihydrofuran-3-one (see mass spectrum, Figure 2) is believed to be

"formed from a fatty acid precursor via the C-hydroxy diketone" [2]. Boelens in
this pubHcation gave mass spectral data for hexyl dihydrofuranone, and we have
found an unknown (pk# 32 on Figure 1) which has a molecular weight 28 mass
units higher, which we have identified as 2-n-octyl-5-methyl-2,3-dihydrofuran-3one (Figure 3).
The volatiles in the extracted oil are not present in the intact tissue of
onion but are produced only when the tissue is injured or cut. The odiferous
components are produced by the enzymatic cleavage of alliins.
Alliins
immediately react with the enzyme alliinase to form alliicin, which then readily
form the mixture of sulfides that are found in the distilled essential oil [24].
Thiolsulfinates, pyruvic acid and ammonia are released by the interaction of the
enzyme alliinase and the precursors, the S-alk(en)yl-L-cysteine sulphoxides [25].
The thiosulfinate is unstable and decomposes to a thiosulfonate and a disulfide.
This explains the presence of alkyl di- and tri-sulfides. The total amount of
pyruvic acid released depends on the pungency of the onion [26].
Other sulfides with lower molecular weights than methyl propyl disulfides
in are unlikely to be found in large percentages in the oil because of their higher
solubility in the water phase of the distillation and their greater volatility.
Therefore the presence of such chemicals as allyl disulfides and alkyl sulfides in
large percentages would indicate tampering with the natural oil. Garlic oil is
abundant in allyl disulfides; therefore any adulteration of onion with garlic will
significantly alter the concentrations of methyl allyl disulfide and 1-propyl-allyl
disulfide. Another indication of adulteration would be the synthetic addition of
allyl disulfides. Synthetic allyl disulfides contain only one of the isomers, while
natural allyl disulfides occur as both the cis- and trans - isomer and at a
characteristic ratio [4].

ACKNOWLEDGMENT
The authors would like to thank Gideon Andemicael, Nehla Azzo and Ben
Benveniste from Kato Worldwide Ltd and Eng. Mohamed Abed Al Al from Kato
Aromatic for their assistance and data used in this paper.

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1
2
3

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Compounds from Onion, J. Agr. Food Chem., 19, 5 (1971) 984.
M.H. Brodnitz, C. L. Pollock, and P.P. Vallon, Flavor Components on Onion
Oil, J. Agr. Food Chem., 17, 4 (1969) 760.

453
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