Attokaran M. Natural Food Flavors and Colorants

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Introduction

Mint has a long history and in earlier days the most popular mint was peppermint.

Although it is not used as much as spearmint, it is well known as a simple ﬂ avor of

popular candies, with a particular emphasis on its cooling effect. Before the present

sophisticated products became common, simple peppermint candies were quite popular

with children.

Medical men such as Dioscorides and Pliny recommended peppermint for various

ailments. In the olden days, mint twigs were used to welcome victorious gladiators

(Farrell 1990 ). Romans and Jews used to grow the plant in connection with their

houses of worship.

Peppermint is native to Mediterranean countries. Like Japanese mint, peppermint

has a large percentage of menthol. The “ pepper ” part of the name is probably derived

from the pungent taste of this mint.

Plant Material

As in other mints, in peppermint the dried aerial part forms the herb from which the

essential oil is obtained. The United States is an important producer of peppermint,

though it is also cultivated in many countries of Europe, South America, and Asia,

and in Australia.

Commercially grown peppermint has two varieties: English or black mint, and

white mint. Black mint is a hardy plant whose yield is higher and is therefore more

commercially important. There is very little cultivation of white mint, but the quality

of oil obtained from this variety is considered superior. Black mint has a violet - brown

stem, while white has a green stem. Both of these varieties are otherwise similar.

The stem is erect, branched, quadrangular, and naked or rarely covered with tri-

chomes (Aktar et al . 1988 ). Leaves are opposite, petiolate, ovate to oblong, and lan-

ceolate. They are 3 – 7 cm in length, serrate at the edges, glabrous or pubescent along

their dossal veins, and punctuated with small oil globules. The surface of the leaf is

glabrous and dark green in color. The color of the ﬂ ower is light purple and ﬂ owers

are arranged in terminal spikes. The calyx is glabrous and dotted and the corolla is

purple, glabrous, and about 5 mm in length.

Peppermint

Mentha piperita L ( Labiatae )

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338 Individual Flavors and Colorants

Harvesting of the aerial part should be carried out when the plant starts to bloom

(Prakash 1990 ). This will ensure a maximum yield of oil and menthol. The oil recovery

suffers rapidly after the full bloom stage, due to the shedding of leaves. In fact, the

loss of oil is greater when harvesting is delayed rather than when it is premature. The

ﬁ rst formed chemical is the ketone menthone, which is transformed to menthol.

The oil content increases up to a certain stage and then decreases. During this time,

free menthol content increases. Hence, the time of harvest is critical.

Drying has to be carefully carried out to reduce loss of oil. Direct sun drying may

result in a loss of as much as 24% due to evaporation and resiniﬁ cation (Prakash

1990 ), so the drying is done in shade when the loss can be restricted to well below

10%. Usually, a satisfactory partial drying can be obtained in 4 – 5 days. Processing of

the dry herbage is more economical and convenient as the yield is obtained faster due

to weakening of oil cells.

On steam distillation, peppermint oil can be obtained from the herb with a yield

of 0.8 – 1%. Although peppermint has a large proportion of menthol, for making pure

crystals of menthol, Japanese mint is more suitable. (For the chemical structure of

menthol, refer to Chapter 62 on Japanese mint.) Almost 50% of the oil is made of

l - menthol, which is responsible for the cooling effect. Next in importance is menthone.

However, a recent Vietnamese study (Nguyen 2003 ) reported that the main constituent

is l - menthone, which is present to a level of 47.60%. Menthone accounted for 24.10%,

menthofuran 6.07%, 1,8 - cineole 5.55%, and pulegone 4.22%. In another study (Orav

et al. 2004 ), variations in composition of peppermint oils produced in different regions

of Europe were examined. The yield obtained varies between 0.8% and 3.3% from

the dried herb. A total of 46 compounds have been identiﬁ ed, representing more than

90% of the oil. The main components are menthone (11.2 – 45.6%), menthol (1.5 –

39.5%), isomenthone (1.3 – 15.5%), menthyl acetate (0.3 – 9.2%), limonene (1.0 – 5.9%),

and trans - sabinene hydrate (traces to 6.2%). There are differences between samples

from different regions. The ratio of menthol to menthone is found to vary between

0.04 and 2.8, and 1,8 - cineole and limonene between 0.3 and 5.0. From the oils of

Greece and Hungary, menthol is seen as the predominant constituent (37 – 40%).

Russian peppermint oil contains only 1.5% menthol but has high menthone (38.2%),

isomenthone (15.5%), and pulegone (13.0%). In Estonian oil, both menthol (31.6 –

35.8%) and menthone (37.9% – 39.5%) are seen in high percentage. In an Iranian study,

after hydrodistillation, menthol (36.24%) and menthone (32.42%) are also found to

be the major constituents (Behnam et al. 2006 ). Studies also show weak antifungal

activity for the essential oil.

Peppermint oil from the semiarid conditions of South India contains menthol

(40.08%) as the major component; other constituents are limonene, menthone, men-

thofuran, pulegone, and menthyl acetate, among 62 peaks in all and 25 major peaks

(Kaul et al. 2001 ).

According to the FCC, peppermint oil is a colorless to pale yellow liquid with

the strong, penetrating odor characteristic of peppermint and a pungent taste together

with a sensation of coolness when inhaled into the month. It can be rectiﬁ ed by dis-

tillation. It is soluble in alcohol and most vegetable oils but insoluble in propylene

glycol.

Physical characteristics of peppermint oil as deﬁ ned by the FCC are as follows.

84 Peppermint 339

Optical rotation − 18 ° to − 32 °

Refractive index 1.459 – 1.465 at 20 ° C

Speciﬁ c gravity 0.896 – 0.908

Solubility 1 mL dissolves in 3 mL of 70% alcohol

Uses

Mint leaves are widely used for garnishing preparations of Asia, Asia Minor, Europe,

and America. In the production of processed foods, it is more convenient to use

the oil.

Peppermint oil is an all - time favorite ﬂ avor for chewing gum, confectionary, ice

cream, and sauces. It also has use in dental preparations and medical preparations for

digestive disorders. Because of its cooling sensation, it is used in tobacco products.

For the same reason, it is used in nonalcoholic beverages, soft drinks, and cookies

(such as cream biscuits).

Identiﬁ cation Numbers

FEMA No. CAS US/CFR E - No.

Peppermint oil 2848 8006 - 90 - 4 182.20 –

98306 - 02 - 6 –

Peppermint oleoresin/extract 2848 8006 - 90 - 4 – –

Peppermint water/absolute – 98306 - 02 - 6 – –

References

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

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

167 – 181 .

Behnam , S. ; Farzaneh , M. ; Ahmadzadeh , M. ; and Tehrani , A. Shariﬁ . 2006 . Composition and antifungal

activity of essential oils of Mentha piperita and Lavendula augustifolia on post - harvest phytopathogens .

Commun. Agric. Appl. Biol. Sci. 71 ( 3b ), 1321 – 1326 ( Chem. Abstr. 148 :2456).

Farrell , Kenneth T. 1990 . Spices, Condiments and Seasonings . New York : Chapman and Hall , pp.

133 – 136 .

Kaul , P.N. ; Bhattacharya , A.K. ; Singh , K ; Rajeswara Rao , B.R. ; Mallavarapu , G.R. ; and Ramesh , S. 2001 .

Chemical investigation of peppermint ( Mentha piperita L) oil . J. Essent. Oil - Bearing Plants 4 ( 2 – 3 ),

55 – 58 .

Nguyen , Thi Phuong Thao . 2003 . Chemical components of the essential oil of Mentha piperita L; collected

from Sapa - Lao Cai and now cultivated in Co Nhue Tu Liem district . Tap Chi Duoc Hoc ( 6 ), 13 – 16

(Vietnamese) ( Chem. Abstr. 140 :326575).

Orav , Anne ; Raal , Ain ; and Arak , Elmar . 2004 . Comparative chemical composition of the essential oil of

Mentha piperita L from various geographical sources . Proc. Estonian Acad. Sci. Chem. 53 ( 4 ), 174 – 181

(English) ( Chem. Abstr. 142 :182771 ).

Prakash , V. 1990 . Leafy Spices . Boston : CRC Press , pp. 49 – 57 .

Introduction

Red sandalwood is a magniﬁ cent tree whose trunk has an attractive natural food colo-

rant. The tree is very important in Ayurvedic therapy because of its medical signiﬁ -

cance. It is an expensive wood very highly valued for making furniture and handicraft

items. Its heavy, thickly packed wood is rated along with other valuable woods such

as teak and rosewood. It is a tree that takes years to grow to full maturity, and con-

servationists are concerned about the population. It is now a protected plant and

therefore, in recent times, its availability for extraction purposes has become a problem.

For this reason, the pigment of red sandalwood has become less and less popular. A

better program for nurturing the trees, tree planting, and exploitation of the chips and

raw dust created as by - products during handicraft making can give an extended life

to the pigments of red sandalwood, known as santalin. The pigment was studied in

mid - nineteenth century by Pelletier and later marketed by E. Merek from 1960

(Verghese 1986 ).

Plant Material

Red sandalwood is a large, attractive deciduous tree. It grows to over 10 m in height

with a well - developed trunk and branches. The trunk has black - brown bark deeply

cleft into rectangular plates. The heart wood is dark purple colored (Warrier 1995 ).

The tree has compound leaves, each with three to ﬁ ve leaﬂ ets. The leaﬂ ets are

broad, elliptical, and obtuse, with pale green undersides. The surface of leaves is

covered with ﬁ ne hair. Its ﬂ owers are yellow, with simple or sparingly branched axil-

lary or terminal recemates . The fruits are oblique pods which narrow into a stalk and

are winged. The central hard portion contains the seed, which is reddish brown and

smooth.

Both the wood and fruit are considered medicinally important. Small pieces of the

wood have a good claret red color due to the natural pigment. In powder form, it gives

off a faint odor resembling that of orris root.

The tree is very hardy and regenerates well. It grows on rocky or dry hills of 250 -

to 700 - m altitude and sometimes on precipitous hillsides in hot dry climate, preferably

with good drainage to avoid waterlogging.

Red Sandalwood

Pterocarpus santalinus L ( Fabaceae )

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342 Individual Flavors and Colorants

Chemistry

The pigment consists of santalins A and B (Fig. 85.1 ). Santalin B has an additional

methyl group compared with santalin A. There is an allied compound designated as

santalin C whose structure is uncertain (Verghese 1986 ). The wood has essential oil

and tannic acid.

Extractive

The santalins are generally required to be a solid crystal powder. For trade purity, the

measure at 475 nm absorbance should not be less than 1 when crystal powder is made

into 0.01% solution in ethanol. This requires not only extraction but also avoidance

of lipids and water - solubles.

The dry wood is made into small pieces and then coarsely powdered in a hammer

mill. After being loaded into a vertical batch percolator, a washing with hexane is

done by pouring solvent on top and allowing it to percolate by gravity. The lipid extract

is taken out and disposed of after recovery of the solvent. The lipids, mainly essential

oil, represent about 1%. The remaining powder is freed of hexane and then extracted

with methanol by gravity percolation until the washings do not have any noticeable

color. The combined methanolic miscella is freed of the solvent. The resinous matter

is then boiled with water. The water extract is removed and disposed of. This process

is repeated so that the residue obtained is a crystalline solid with good characteristic

color and absorption value as described above. Experience shows that about four

washings will yield a solid santalin of required strength. The solid is then dried and

ground as per customers ’ speciﬁ cation.

For ease of handling, sometimes santalin in liquid form is needed. This is made by

adding an equal weight of propylene glycol after solids appear on removal of methanol

but before water washings.

Santalin crystals soften at 223 – 268 ° C depending on purity, but at 270 ° C they turn

into a carbonaceous mass, as they decompose on melting.

Figure 85.1. Santalin. Santalin A: R = OH; santalin B: R = OMe.

OMe

MeO

85 Red Sandalwood 343

Uses

Red sandalwood extract is used as a natural color in foods and alcoholic beverages.

Unreﬁ ned color has always been used in India. Until recently, the color was very much

in demand in Europe for use in fruit products, beverages, and candies. However, the

European Commission has not accorded it an E - number. This fact, along with the

restriction of its use in India due to conservation of the tree, may make this attractive

color less and less available.

Ayurvedic therapy attributes many useful medical properties to red sandalwood

such as antipyretic and anthelmintic. Made into paste, it is applied to relieve inﬂ am-

mation, eye swelling, and boils. For bleeding piles, the powder is mixed in milk and

ingested. The wood paste is regarded as a coolant and skin puriﬁ er.

Analytical Method

The empirical method generally used by the industry is by measuring the absorbance

at 475 nm. A value of 1 in a solution in ethanol at 0.01% strength is regarded as a

satisfactory crystal powder.

Identiﬁ cation Numbers

FEMA No. CAS US/CFR E - No.

Sandalwood red – 84650 - 41 - 9 172.510 166

References

Verghese , James . 1986 . Santalin — a peerless natural colourant . Cosmet. Toiletries 101 , 69 – 71 .

Warrier , P.K. 1995 . Indian Medicinal Plants . Madras : Orient Longman , vol. 4 , pp. 384 – 387 .

Introduction

The history and romance of rosemary are as fascinating as the herb itself. It has value

as a ﬂ avor, fragrance, medicine, and, in recent years, antioxidant.

There is a story from a source at Trinity College library, Cambridge, that Queen

Philippa ’ s mother, Countess of Hainault, sent the ﬁ rst plant to England. Rosemary has

since thrived there. In Spain, people consider it to be the bush that gave shelter to the

Virgin Mary while traveling to Egypt, and in honor of that they refer to it as Romero,

the pilgrim ’ s ﬂ ower, from which the popular name arose. In the Mediterranean coun-

tries, it is believed to give protection from witches and other evil spirits. All parts of

the plant are considered useful to give protection from some disease or other and to

generally uplift the health and spirits.

Ancient people used rosemary with the belief that it would strengthen memory and

act as an emblem of ﬁ delity. It is used at wedding and funerals. Rosemary was also

cultivated in the kitchen garden as a symbol of the dominant inﬂ uence of the mistress

of the house. In Shakespeare ’ s Hamlet , Ophelia distributes rosemary ﬂ owers as a

symbol of remembrance. Rosemary leaves were used to ﬂ avor tea and wine. As for

its medical beneﬁ ts, rosemary is included in many recipes suggested for various

diseases.

Plant Material

Rosemary is a small evergreen shrub cultivated in Mediterranean countries such as

Spain, Portugal, Italy, Yugoslavia, Turkey, Tunisia, and Algeria, as well as in the

United States. The heavily branched plant grows to about 2 m. Its leaves are needle -

like with a length of 2 – 3 cm, shaped like curved pine needles. The plant has small,

light blue ﬂ owers.

Rosemary is propagated by seeds, cuttings, and division of roots. The healthiest

plants are reported to be grown from seeds. The best condition for growth is light,

somewhat dry soil. It prefers a bit of shade. When dried, the herb assumes a brownish -

green color and has a tea - like aroma. However, when crushed, the aroma is more

pleasant with a spicy and camphoraceous note. The taste is fragrant, spicy, and

pungent, with a bitter note.

Rosemary

Rosmarinus ofﬁ cianalis L

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