Attokaran M. Natural Food Flavors and Colorants

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186 Individual Flavors and Colorants

of oil, or quality of oil was noticed by drying for longer duration. Steam is admitted

at low pressure and distillation is allowed to proceed very slowly. After 8 hours, the

yield obtained is 0.07 – 0.1 on the basis of original fresh weight. The oil obtained is a

slightly oily liquid with a reddish - yellow color and a fragrant, herbal, and fruity aroma.

Davanone content is generally 45%. With fractional steam distillation and by restrict-

ing the yield of oil to 0.05%, the davanone content can be raised to above 50%.

Physical characteristics are as follows.

Optical rotation + 40 ° to + 60 °

Refractive index 1.4780 – 1.4900 at 25 ° C

Speciﬁ c gravity 0.9200 – 0.9800

Aktar et al. (1988) have summarized the early work on this plant very well. The

most important constituent is a ketone, davanone, which is usually present to the extent

of 50 – 60% in good quality oil. In fact, pricing is dependent on the davanone content.

Fenchyl alcohol, cinnamyl cinnamate, caryophyllene, cadenene, and some phenols

and acids have been reported. Some of the alcohols noted are linalool and dehydro -

α - linalool. Davanafuran, isodavanone, dihydrorosifuran, nor - diterpenoid furan deriv-

atives, n - alkanes, hydroxyl davanone, geraneol, and nerol are the other constituents

found in the oil. The chemical structure of davanone (Catlan et al. 1990 ) is presented

in Fig. 47.1 .

Recently, davana has been introduced in Kashmir, in the north of India, where it

has proved to yield a high davanone content. GC - MS studies show the components

to be davanone (74.59%), ethyl cinnamate (8.40%), β - eudesmol (3.20%), methyl cin-

namate, davanol isomers 1 and 2, and other compounds (Shawl et al. 2009 ).

Uses

Davana oil is a highly prized ﬂ avor for expensive food and beverage products such

as liquor and liqueurs. It is also used in perfumery. The crop is grown only in India,

but the appeal of the oil is universal.

The ﬂ owers themselves are valued more for their fragrance and aroma rather than

for their attractiveness when used for temple offerings and for adorning women ’ s hair.

Identiﬁ cation Numbers

FEMA No. CAS US/CFR E - No.

Davana oil 2359 8016 - 03 - 3 172.510 –

91844 - 86 - 9 –

Figure 47.1. ( + ) Davanone.

47 Davana 187

References

Aktar , Husain ; Virmani , O.P. ; Sharma , Ashok ; Kumar , Anup ; and Misra , L.N. 1988 . Major Essential Oil -

Bearing Plants of India . Lucknow, India : Central Institute of Medicinal and Aromatic Plants , pp.

84 – 86 .

Catlan , Ceasar A.N. ; Cuenca , Maria Dell ; Verghese , James ; Joy , M.T. ; Gutierrez , Alicia B. ; and Hertz ,

Werner . 1990 . Sesquiterpene ketones relating to davanone from Artemisia pallens . Phytochemistry 29

( 8 ), 2702 – 2703 .

Guenther , Ernest . 1952 . The Essential Oils . Malabar, FL : Robert, E. Krieger Publishing Company , vol. 5 ,

pp. 451 – 453 .

Shawl , A.S. ; Rather , M.A. ; and Kumar , T. 2009 . Essential oil composition of Artemisia pallens (davana)

cultivated in Kashmere valley, India . Indian Perfumer 53 ( 3 ), 35 – 37 .

Introduction

Dill is used in Europe for its soothing effect on the digestive system. It is indigenous

to the Mediterranean region and the south of Russia. There is a belief that dill origi-

nated in Eastern Europe, but wild dill is found widely in the Mediterranean region

and West Asia.

Dill was regarded as a magic herb in Medieval Europe where brides used to wear

a small branch in their hair and footwear for good fortune. Mexicans believed that dill

could protect them from witchcraft and evil spirits. There is evidence that dill was

used in Babylonia and Syria. Romans used it as a stimulant for their gladiators.

Later dill became a staple of Northern European cuisine. Both dill seed and dill

weed have gained popularity in North America. The name is perhaps derived from

Norse word dilla , which means “ to lull ” since it was used to lull babies to sleep as

well as to get relief from stomach disorders.

Plant Material

Dill seed is the dried fruit of an annual (or occasionally biennial) herb which belongs

to the parsley group. European dill is Anethum graveolens L; Indian dill is Anethum

sowa DC. The former is grown in Egypt, Mediterranean countries, Eastern Europe,

North America, and some parts of Latin America. A. sowa is grown mainly in India.

Dill herb grows to a height of 90 cm. The leaves are dissected with a clasping base.

The fully grown leaf is 50 cm long and a little less than 30 cm in maximum spread.

Its ﬂ owers are light yellow in color. Dill seeds are brown in color and have an oval

shape. One side is nearly ﬂ at with two longitudinal ribs. The other side is convex with

three ribs. The length of the seed is about half a centimeter. The Indian variety ’ s seeds

are slightly bigger, but have less of an aroma. Photo 13 shows the Indian dill plant

and seeds.

The leaves and stalks of the dill plant are also aromatic. These, in fresh condition

together with immature fruits, are known as dill weed or herb and are used in pickling

and in soups.

Chemistry

The main constituent is carvone (see Chapter 27 on caraway seed). Indian oil from A.

sowa has a somewhat toxic constituent known as dillapiole (Fig. 48.1 ). This is a high -

boiling heavy fraction (density 1.163 g/mL) with a structure close to that of apiole.

Dill

Anethum graveolens L, A. sowa DC ( Umbelliferae )

189

Natural Food Flavors and Colorants Mathew Attokaran

Photo 13. (A) Dill plant. (B) Dill seed. See color insert.

190

48 Dill 191

Essential Oil

Although dill seed oil used to be made in different parts of the world including the

United States, today India has emerged as the major producer.

Seeds are size - reduced by passing through a roller mill and then fed into a stainless

steel distillation unit. Steam is introduced at normal pressure and distillation continues

for 24 hours, to obtain a yield of 2.4% without cutting the dillapiole fraction.

The oil is a pale yellow to brownish liquid. The main constituent is carvone, which

is present in 30 – 60%. Other major constituents are α - phellandrene, 3,9 - epoxy - p -

menth - 1 - ene, myrcene, p - cymene, and limonene.

Especially for pharmaceutical use and use in food, it is necessary to remove dil-

lapiole by fractional vacuum distillation. Since it is a heavy fraction, it distills out last

and can be easily removed. Generally, it is better to use a two - stage vacuum distilla-

tion. The ﬁ rst stage separates the lower boiling fraction from the heavy fraction. The

second stage is to recover the low boilers from the separated heavy dillapiole fraction,

so as to get a satisfactory yield of good oil.

Dill oil from Reunion Island reveals 36 components with α - phellandrene (56.5%),

dill ether (20.8%), limonene (10.9%), and p - cymene (3.8%) accounting for 92% of

the oil (Vera and Chane - Ming 1998 ). Indian dill oil, when analyzed using GC - MS,

shows 21 compounds, with limonene (42.67%), carvone (22.50%), and dillapiole

(15.92%) being the main ones (Shankaracharya et al. 2000 ). It is surprising, however,

that dillapiole is seen in high proportion in A. graveolens by Vietnamese workers (Le

et al. 2006 ). They found α - phellandrene (44.21%), β - phellandrene (11.01%), and dil-

lapiole (27.69%).

The FCC describes European dill seed oil as a pale yellow to light yellow liquid

with a caraway odor and ﬂ avor. It is soluble in most ﬁ xed oils and in mineral oils. It

is soluble with slight opalescence in propylene glycol but it is practically insoluble in

glycerin.

Physical characteristics of oil from A. graveolens (European type) as deﬁ ned by

the FCC are as follows.

Optical rotation + 70 ° to + 82 °

Refractive index 1.483 – 1.490 at 20 ° C

Speciﬁ c gravity 0.890 – 0.915

Solubility 1 mL dissolves in 2 mL 80% alcohol

According to the FCC, Indian dill seed oil occurs as a light yellow to light brown

liquid with rather harsh caraway odor and ﬂ avor. It is soluble in most ﬁ xed oils and

Figure 48.1. Dillapiole.

OCH

192 Individual Flavors and Colorants

in mineral oil, occasionally with slight opalescence. It is sparingly soluble in propylene

glycol and practically insoluble in glycerin.

Physical characteristics of oil from A. sowa (Indian type) as deﬁ ned by the FCC

are as follows.

Optical rotation + 40 ° to + 58 °

Refractive index 1.486 – 1.495 at 20 ° C

Speciﬁ c gravity 0.925 – 0.980

Solubility 1 mL dissolves in 0.5 mL of 90% alcohol

American - type dill weed oil, according to the FCC, is a light yellow to yellow

liquid. It is soluble in most ﬁ xed oils and in mineral oil. It is soluble, with opalescence

or turbidity, in propylene glycol but it is practically insoluble in glycerin.

Physical characteristics of the above are as follows.

Optical rotation + 84 ° to + 95 °

Refractive index 1.480 – 1.485 at 20 ° C

Speciﬁ c gravity 0.884 – 0.900

Solubility 1 mL dissolves in 1 mL of 90% alcohol, frequently with

opalescence, which may not disappear on dilution to as

much as 10 mL

There is very little production of dill oleoresin, oil being the well - used extractive.

However, a CAS number is given for extract.

Dill weed oil, consisting of oil from the leaves and immature fruits, is different

from dill seed oil. Dill seed oil is pungent and reminiscent of caraway, while dill weed

or herb oil has a mellow and fresh ﬂ avor. Dill weed oil contains carvone, α - and β -

phellandrene, and monoterpenes.

Uses

Since both dill seed and herb are used in pickling, salad dressings, and processed food,

especially meat, cheese, and bread, oil can replace either in processed food.

Dill seed oil has therapeutic value due to its antispasmodic, carminative, diuretic,

and stomachic properties. One of the largest outlets for dill oil, especially in India, is

for use in “ gripe ” mixture, which is administered to babies to give relief from stom-

achache and related ailments.

Identiﬁ cation Numbers

FEMA No. CAS US/CFR E - No.

Dill ( A. graveolens ) 2382 8006 - 75 - 5 184.1282 –

Dill seed oil ( A. sowa ) 2384 8016 - 06 - 6 172.510 –

Dill weed oil 2383 8006 - 75 - 5 184.1282 –

90028 - 03 - 8

Dill seed extract – 8006 - 75 - 5 – –

84775 - 84 - 8

Dill weed oleoresin 2382 – – –

48 Dill 193

References

Le , Van - Hac ; Do , Thi Ninh ; and Nguyen , Xuan Dung . 2006 . Study on chemical composition of the essential

oil of Anethum graveolens L from Nghe An and Ha Tinh . Tap Chi Duoc Hoc 46 ( 5 ), 28 – 29 , 31

(Vietnamese) ( Chem. Abstr. 146:235416).

Shankaracharya , N.B. ; Rao , L. ; Jagan , Mohan ; Puranaik , J. ; and Nagalakshmi , S. 2000 . Studies on chemical

and technological aspects of Indian dill seed ( Anethum sowa Rxb) . J. Food Sci. Technol. 37 ( 4 ),

368 – 372 .

Vera , R.R. ; and Chane - Ming , J. 1998 . Chemical composition of essential oil of dill ( Anethum graveolens

L) growing in Reunion Island . J. Essent. Oil Res. 10 ( 5 ) 539 – 542 .

Introduction

Ancient scholars considered fennel seeds to be endowed with many characteristics

which promote an active and healthy life. Aside from this, it has also been regarded

as a spice valuable in cooking. In India, it is also used as a masticatory after a heavy

meal, as it acts as a mouth freshener and an aid to good digestion.

In ancient times, fennel was believed to have some esoteric uses. In Greece, fennel

is regarded as a symbol of success. In Rome, young fennel shoots were eaten as food.

It is believed to improve vision and even to be an antidote for poison. Other uses

attributed to the seed are rejuvenator, to stop hiccups, to cure wheezing, to ease

stomach pain, to give additional milk to nursing mothers, to be good for the kidneys,

and so on.

Plant Material

Fennel is a perennial or biennial plant which grows to a height of 1.5 – 2 m. India is a

major producer, but it is also grown in Eastern European, Mediterranean, and North

African countries. Its seeds are bigger than those of cumin and are greenish in color,

with a length of 5 – 7 mm (Photo 14 ). The seeds have longitudinal ridges, sometimes

slightly curved. India is a major consumer of fennel seeds.

Fennel seed has 1 – 6% of essential oil. The oil content of the average Indian variety

is about 1%. The seed has about 10 – 15% ﬁ xed oil. The fatty acid composition shows

about 60% petroselinic acid, 22% oleic acid, 15% linoleic acid, and the rest mostly

palmitic acid. It has many vitamins, such as vitamin A, ascorbic acid, thiamine, ribo-

ﬂ avin, and niacin. But it must be remembered that the amount of fennel seeds eaten

in a day is very limited and hence its nutritional advantages should not be taken seri-

ously. Fennel spice has a mild, pleasant, spicy aroma and a slightly sweet taste.

Essential Oil

Steam distillation of size - reduced fennel seeds yields an essential oil. Only coarse

grinding is necessary and for this it is best to pass through a roller mill. Coarsely

Fennel

Foeniculum vulgare Miller ( Umbelliferae )

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Natural Food Flavors and Colorants Mathew Attokaran