Attokaran M. Natural Food Flavors and Colorants

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226 Individual Flavors and Colorants

Uses

Ginger as a spice is used all over the world for its special pungency and typical aroma.

Most savory foods use it. Ginger is used in bakery products such as gingerbread and

biscuits. Similarly, ginger is a favorite ingredient in soft drinks. When conventional

foods are made into processed products, ginger oil and oleoresin replace ground

ginger. Many meat, seafood, and vegetable preparations, as well as snacks, dressings,

and soups, can be ﬂ avored by ginger oleoresins. Oleoresins give mild pungency in

addition to aroma.

Candied ginger ﬁ nds use in bakery and confectionery items. Ginger is regarded as

a digestive and therefore ginger oleoresin can be used in preparations for this beneﬁ t.

Gingerol may reduce nausea caused by motion sickness or pregnancy (Ernst and Pittler

2000 ).

Identiﬁ cation Numbers

FEMA No. CAS US/CFR E - No.

Ginger oil 2522

{

8007 - 08 - 7 182.20 –

84696 - 15 - 1

Ginger oleoresin 2523

{

84696 - 15 - 1 182.20 –

8002 - 60 - 6

Ginger extract 2521

{

86696 - 15 - 1 182.20 –

8007 - 08 - 7

References

Connell , D.W. 1969 . The pungent principles of ginger and their importance in certain ginger products . Food

Technol. Aust. 21 , 570 – 574 .

Connell , D.W. ; and Sutherland , M.D. 1969 . A reexamination of gingerol, shogaol and zingerone in the

pungent principles of ginger ( Zingiber ofﬁ cinale Rosc.) . Aust. J. Chem. 22 , 1033 – 1037 .

Ernst , E. ; and Pittler , M.H. 2000 . Efﬁ cacy of ginger for nausea and vomiting: a systematic review of

randomized clinical trials . Br. J. Anaesth. 84 ( 3 ), 367 – 371 .

Govindarajan , V.S. 1982 . Ginger — chemistry, technology and quality evaluation. Part 2 . Crit. Rev. Food

Sci. Nutr. 17 ( 3 ), 189 – 258 .

Lawrence , B.M. 1984 . Major tropical spices — ginger Zingiber ofﬁ cinale Rosc . Perfumer Flavorist 9 ( 5 ),

1 – 40 .

Lawrence , Brian M. 2008 . Progress in essential oils . Perfumer Flavorist 33 ( 6 ), 58 – 71 .

Nirmala , Menon ; Padmakumari , K.P. , Sankarikutty , B. ; Sumathikutty , M.A. ; Srikumar , M.M. ; and

Arumughan , C. 2007 . Effects of processing on the ﬂ avour compounds of Indian fresh ginger Zingiber

ofﬁ cinale R . J. Essent. Oil Res. 19 , 105 – 109 .

Peng , Weixin ; Zhang , Yangde ; Yang , Ke ; and Xiao , Yecheng . 2007 . Chemical constituents of Zingiber

ofﬁ cinale ( Zingiberaceae ) . Yunnan Zhiwu Yanjiu 29 ( 1 ) 125 – 128 ( Chem. Abstr. 149:466255).

Introduction

Grapes are a popular food item, used as a table fruit; as fruit products such as nonal-

coholic beverages, juice concentrates, and jam; and as a fermented alcoholic beverage,

wine. Brandy is a distilled alcoholic drink made from wine. When grapes are eaten

alone and in preparations like fruit salad, the hard seed is undesirable and so seedless

grapes have been developed. When excess fruit is available due to short shelf life, it

may be dried and converted into raisins for use in baked products, puddings, and other

sweet preparations.

Statistics have shown that French people, despite eating fatty foods, have a lower

incidence of heart - related disorders. Researchers have concluded that some antioxi-

dants, mainly resveratrol, present in the grape skin could be the key. This polyphenolic

compound is an effective antioxidant and can be positively linked to inhibiting cancer,

heart disease, degenerative nerve disorders including Alzheimer ’ s disease, and some

viral infections.

The natural food color present in the grape is anthocyanin and is found mostly in the

skin of crimson, black, or dark blue grapes. Generally, during wine making, a high

percentage of anthocyanin pigment remains in the spent skin after the liquid wine is

decanted out. In normal processing for fruit products, skin and seeds are removed so

that a homogeneous clear liquid will be obtained. Such skin that comes out as by -

products is a good raw material for preparation of anthocyanin - based natural food color.

Plant Material

Grapes grow on perennial and deciduous woody vines belonging to the genus Vitis .

This genus has about 60 species that are all vining plants with ﬂ owers. Vitis plants

have petals that are joined at the tip and detach from the base when falling as a cap.

The calyx is very small. There are both sterile and fertile ﬂ owers. Sterile ﬂ owers have

ﬁ ve long ﬁ laments, erect stamens, and poorly developed pistils. Fertile ﬂ owers, on the

other hand, have well - formed pistils with ﬁ ve stamen. Four or fewer fruits will be

formed from a ﬂ ower through aborted embryos. The fruits are round and juicy and

can be botanically considered to be a true berry. It is a nonclimacteric fruit.

Although in the wild, the grape is generally dioecious, under developmental agri-

culture, the right variants with bisexual characteristics have been selected. Grapes

are cultivated in different regions all around the world. This has resulted in plants of

Grape

Vitus vinifera L ( Vitaceae )

227

Natural Food Flavors and Colorants Mathew Attokaran

228 Individual Flavors and Colorants

different characteristics adapting to the agro - climatic conditions and requirements of

the desired fruit quality. The top four grape producers are Italy with 8.52 million

tonnes, China with 6.79 million tonnes, the United States with 6.38 million tonnes, and

France with 6.04 million tonnes of grapes annually as per the data of the FAO for

2009. Other major producers are Spain, Turkey, Iran, Argentina, Chile, and India.

On a wet basis, the fruit has 18.1% carbohydrate, of which 15.5% is sugar; 0.16%

of fat; and 0.72% of proteins. It is rich in B vitamins, ascorbic acid, and minerals.

While primary use of the grape is as a fruit and as a raw material for wine making,

only the skin of highly colored ones are the raw material for extraction of color.

Chemistry

Grape colors are anthocyanins, which are glycosides of anthocyanidins. The structure

of anthocyanidins is presented in Fig. 57.1 . Anthocyanins occur in a dissolved state

in the cell sap of ﬂ owers, fruits, and other parts and are generally present as glycosides.

On boiling with 20% hydrochloric acid for about 3 minutes, anthocyanins become

hydrolyzed to yield anthocyanidins and one or more sugar moieties. The most com-

monly found sugars are glucose, galactose, rhamnose, and, in a few cases, gentibiose

and xylose. These are, in the majority of cases, attached to 3 position and, less fre-

quently, the 5 position.

Based on hydroxyl groups, anthocyanidins are pelargonidin, cyanidin, and delph-

inidin. In addition, methylated derivatives are present. Delphinidin with three hydroxyl

groups will have very slight reddish tint, while pelargonidin with only one hydroxyl

group will have very slight bluish tint.

The most common anthocyanidins in grape skin are peonidin, malvidin, delphini-

din, and petunidin (Leung and Foster 1996 ). Of these, all except delphinidin are acyl-

ated compounds, which are more stable to conditions such as heat, light, and chemical

reduction. They are also less affected by changes in pH.

Extractives

Grape skin anthocyanins are extracted with water or aqueous ethanol; pure alcohol is

a very poor solvent. It is stable at the acidic pH of 3. As the pH is increased to neutral

and further to 8, the color changes from red to purple and blue.

Figure 57.1. Anthocyanidins. Pelargonidin: R

= H, R

= OH, R

= H; cyanidin: R

OH, R

= OH, R

= H; delphinidin: R

= OH, R

= OH; peonidin: R

= OCH

= OH, R

= H; malvidin: R

= OCH

, R

= OH, R

= OCH

; petunidin: R

= OH, R

OH, R

= OCH

57 Grape 229

The blue - black grape variety is the best source for anthocyanins. Generally, while

extracting with water, a small percentage of sulfur dioxide helps to prevent fermenta-

tion activity caused by natural spoilage of the yeast present in the skin. The aqueous

extract separated from solids and concentrated gives a pigment strength of 1% in liquid

form (Emerton 2008 ). Anthocyanins are more stable in acidic pH, generally as a salt

of chloride or other ions.

As in most plant products, grapes have minor amounts of leucoanthocyanidins,

which on treatment with hot acid become converted to anthocyanidin salt of the acid

used. But in the extract, these proanthocyanidins are colorless.

In a recent study, Syrah grapes harvested at different stages showed nine anthocya-

nins. The total amount of anthocyanins during ripening was signiﬁ cantly higher in

conventionally grown grapes than the amount found in organic production (Vian et al.

2006 ).

In red wine, the pigment concerned is anthocyanin. But on long aging, anthocyanins

coming from grapes turn into secondary pigments, which are responsible for the

color of old wines (Kennedy 2008 ). Resveratrol, an antioxidant in grapes, has

acquired prominence in recent years. This component is regarded as responsible

for the beneﬁ cial effect of red wine for many diseases and conditions (Creasy and

Creasy 1998 ).

Uses

With the rising trend of using natural colors instead of synthetic colors, anthocyanins

are useful for giving red - related colors. The pigment is soluble in water and not in

fat, and so it is suitable for water - based products. It is stable at acid pH and therefore

fruit juice and wine are most suitable for its use. Chilling helps its stability during

storage.

Grape extract is used for coloring red - tinted fruit products like black currant drinks,

jams, preserves, and yogurt. Sourish products that have an acidic pH, such as boiled

sweets, gums, jellies, dry mix desserts, and drink powders, are ideal for using

grape anthocyanin colors. Because of their freezing temperatures, ice creams can be

colored with grape extract. One of the main uses is in supplementing the color of red

wines.

Analytical Method

The AOAC has a method of determining anthocyanin levels in fruits using paper

chromatographic separation, elution, and reading at the maxima for the concerned

compound. The maxima of anthocyanins are in the region of 540 – 560 nm.

Identiﬁ cation Numbers

FEMA No. CAS US/CFR E - No.

Anthocyanins – – – 163(i)

Grape skin extract – – – 163(ii)

Black currant extract – – – 163(iii)

230 Individual Flavors and Colorants

References

Creasy , L.L. ; and Creasy , M.T. 1998 . Grape chemistry and signiﬁ cance of resveratrol: an overview . Pharm.

Biol. 36 , 8 – 13 .

Emerton , Victoria , ed. 2008 . Food Colours . Oxford, UK : Leatherhead Publishing and Blackwell Publishing

Company , pp. 9 – 15 .

Kennedy , James A. 2008 . Chemistry of red wine colour . In Colour Quality of Fresh and

Processed Foods , ASC Symposium Series 983. Oregon State University, Corvallis, OR ( American

Chemical Society) , pp. 168 – 184 .

Leung , Albert Y. ; and Foster , Steven . 1996 . Encyclopedia of Common Natural Ingredients . New York : John

Wiley and Sons , pp. 288 – 289 .

Vian , Maryline Abert ; Tomao , Valerie ; Coulomb , Philippe Olivier ; Lacombe , Jean Michel ; and Dangles ,

Olivier . 2006 . Comparison of anthocyanin composition during ripening of Syrah grapes grown using

organic or conventional agricultural practices . J. Agric. Food Chem. 54 ( 15 ), 5230 – 5235 .

Introduction

Grapefruit is a bitter fruit that grows on a subtropical citrus tree. It originated in the

Caribbean islands. Although there is a theory that it was a gift from the New World

to the Old World, research has shown that it originated in the Old World. It is probably

a hybrid of the Jamaican sweet orange ( Citrus sinensis ) and the Indonesian pomelo

( Citrus maxima ). It is believed that Captain Shaddock brought pomelo seeds to

Jamaica and bred grapefruit during the eighteenth century. In Barbados, it was ﬁ rst

named “ forbidden fruit, ” probably because of bitterness. It is also called Shaddock

after its creator. However, the popular and current name “ grapefruit ” came from the

fact that fruit on the tree grows in clusters and often appears similar to grape bunches.

In the present times, grapefruit has become a valuable agricultural product of

Barbados. In the early nineteenth century, it was introduced in Florida. Development

of the Ruby Red variety in the twentieth century made the fruit an important agricul-

tural product in Texas. The latest is Rio Red, which is promoted as Reddest and Texas ’

choice.

The major uses of most citrus fruits are as fruit or as a source of fruit juice.

Grapefruit have a strong ﬂ avor, but it is not widely used in ﬂ avoring other food prod-

ucts. The ﬂ avor that is obtained is the oil that is extracted from the peel. Thus, the

major food product is the fruit itself; the peel oil is a by - product. However, peel oil,

being a valuable ﬂ avor, contributes substantially to the economy of the citrus

industry.

Plant Material

The tree on which grapefruit grows is large, with a height of up to 10 m. There are

numerous cultivars developed by hybridization, so it is difﬁ cult to give a brief standard

description. The fruits are generally large.

The source of grapefruit essential oil is the rind or peel of the fruit. The diameter

of an American grapefruit is between 9.5 and 14.5 cm. In the early days of its cultiva-

tion, fruits with seeds such as the Duncan variety were the main type grown in Florida.

However, toward the end of the nineteenth century, the marsh Seedless variety was

introduced. Both these types are now grown (NIIR Board 2009 ). Presently, the United

States is more than self - sufﬁ cient in grapefruit production, compared with earlier years

when the fruit was imported from South Africa.

Grapefruit

Citrus paradisi Mae fayden ( Rutaceae )

231

Natural Food Flavors and Colorants Mathew Attokaran

232 Individual Flavors and Colorants

Oil glands are located deep in the grapefruit peel, which also contains a thick layer

of sponge - like albedo.

According to an FAO estimate of 2007, the United States is the main producer of

grapefruit with a production ﬁ gure of 1,580,000 tonnes per year. Other major produc-

ers are China (547,000 tonnes), South Africa (430,000 tonnes), Mexico (390,000 tonnes),

and Syria (290,000 tonnes). Others, in descending order, are Israel, Turkey, India,

Argentina, and Cuba, with production ﬁ gures ranging from 290,000 to 175,000 tonnes.

Essential Oil

Grapefruit oil is produced by cold expression. Because of the location of oil cells, that

is, deep inside the peel, there is a chance for the spongy albedo to absorb the oil as

soon as it is released from the ﬂ avedo (NIIR Board 2009 ). Even with moderate pres-

sure, the yield of oil is low compared with that of an orange or lemon. With screw

presses, the yield is only around 0.06%. This is far less than the theoretical yield of

1.25% obtained by steam distillation of the minced peel. But by using special peel

press oil, a yield of 0.09% is achievable.

The chemical investigations on the constituents of grapefruit essential oil are rather

old, and very few reports have been published in recent years. Leung and Foster (1996)

have reviewed the subject excellently and a summary of it is given here. The main

constituent is the most characteristic constituent of citrus fruits, limonene. Changes

during irradiation have been studied and investigators have found that d - limonene and

myrcene contents become reduced due to irradiation (Vanamala et al. 2005 ). In the

fruit itself, they found that irradiation helps to preserve ﬂ avonoids such as naringin

and narirutin. Lycopene content is found to be affected, while β - carotene is preserved

in irradiated lots as compared with the control. Other volatile compounds reported in

the grapefruit are sesquiterpenes (cadinene and paradisiol), aldehydes (neral, geranial,

perellaldehyde, citronellal, α - sinensal, and β - sinensal), esters (geranyl acetate, neryl

acetate, perillyl acetate, octyl acetate, decyl acetate, citronellyl acetate, trans - carvyl

acetate, 1,8 - p - menthadien - 2 - yl acetate, and 1,8 - menthadiene - 9 - yl acetate), and a dicy-

clic sesquiterpene ketone, nootkatone (Guenther 1949 ; Leung and Foster 1996 ). Other

components reported are coumarins and furocoumarins (bergaptens). The typical bit-

terness of the fruit is due to naringin, the bulk of which is present in the peel. The

aroma of the grapefruit is caused by nootkatone and esters such as geranyl acetate,

neryl acetate, octyl acetate, and 1,8 - p - menthadien - 2 - yl acetate (Leung and Foster

1996 ).

Various alcohols, carbonyls including aldehydes, monoterpenes, and sesquiterpenes

have been reported in cold - pressed grapefruit oil (Nagy et al . 1977 ). One sesquiterpene

ketone, nootkatone, is shown to be responsible for grapefruit oil ’ s ﬂ avor (MacLeod

and Buigues 1964 ).

Recently, a cyclic acetal of marmin and two cyclic acetals of 6 ′ ,7 ′ - dihydroxy

bergamotin have been isolated from grapefruit peel oil by Cesar et al. (2009) . They

also found previously reported compounds of marmin, bergamotin, and dihydroxy

bergamotin.

Generally, citrus oil, especially limonene, is affected by oxidation, particularly in

the presence of moisture. Moisture alone without air may be endured during storage.

Avoidance of air is beneﬁ cial in extending storage life, so providing an inert carbon

58 Grapefruit 233

dioxide atmosphere and, to a lesser extent, keeping container full and tightly closed

aid in this purpose. Cool storage temperatures are helpful.

As in other citrus oils, removal of terpene hydrocarbons will improve the ﬂ avor.

Similarly, a naringin - rich fraction will give bitter taste to products, which is welcome

in some cases.

Cold - pressed grapefruit oil, according to the FCC, is a yellow and sometimes red

liquid, which often shows a ﬂ occulent separation of waxy material. It is soluble in

most ﬁ xed oils and in mineral oil, often with opalescence or cloudiness. It is slightly

soluble in propylene glycol and insoluble in glycerin. It may contain suitable

antioxidants.

Physical characteristics as deﬁ ned by the FCC are as follows.

Optical rotation + 91 ° to + 96 °

Refractive index 1.475 – 1.478 at 20 ° C

Speciﬁ c gravity 0.848 – 0.856

Uses

Grapefruit essential oil is a valuable citrus oil used in various foods such as baked

goods, puddings, candy, and dairy - based desserts. Both alcoholic and nonalcoholic

beverages are ﬂ avored with the oil. A naringin - rich fraction gives a welcome bitter-

ness, if used in the right proportion, for alcoholic beverages, soft drinks, some special

baked products, and even candies.

Grapefruit oil is not injurious to skin and is used in some cosmetics and

toiletries.

Identiﬁ cation Numbers

FEMA No. CAS US/CFR E - No.

Grapefruit oil, expressed 2530 8016 - 20 - 4 182.20 –

90045 - 43 - 5 –

Grapefruit oil, terpeneless 90045 - 43 - 5 182.20 –

References

Cesar , T.B. ; Manthey , J.A. ; and Myung , K. 2009 . Minor furan coumarins and coumarins in grapefruit peel

oil as inhibitors of human cytochrome P4503A4 . J. Nat. Prod. 72 ( 9 ), 1702 – 1704 .

Guenther , Ernest . 1949 . The Essential Oils . Malabar, FL : Robert E. Krieger , pp. 347 – 359 .

Leung , Albert Y. ; and Foster , Steven . 1996 . Encyclopedia of Common Natural Ingredients . New York : John

Wiley and Sons , pp. 286 – 287 .

MacLeod , W.D. ; and Buigues , N.M. 1964 . Sesquiterpenes 1. Nootkatone, a new grapefruit ﬂ avour constitu-

ent . J. Food Sci . 29 , 565 – 568 .

Nagy , Steven ; Shaw , Philip E. ; and Veldhuis , Matthew K. 1977 . Citrus Science and Technology .

Westport, CT : AVI Publishing , vol. 1 , p. 438 .

NIIR Board . 2009 . The Complete Technology Book of Essential Oils . Delhi : Asia Paciﬁ c Business Press ,

pp. 231 – 238 .

Vanamala , Jairam ; Cobb , Greg ; Turner , Nancy D. ; Lipton , Joanne R. ; Yoo , Kil Sun ; Pike , Leonard M. ; and

Patil , Bhimanagouda S. 2005 . Bioactive compounds of grapefruit ( Citrus paradisi cv Rio Red.) . J. Agric.

Food Chem. 53 ( 10 ), 3980 – 3985 .

Introduction

Chlorophyll, which is present in green leaves, became very important during the early

twentieth century when it was used in toothpaste. Chlorophyll toothpaste became quite

popular, as chlorophyll was thought of as a way to produce an active oxygen atmo-

sphere in the mouth. Many dental experts felt that bad breath in the mouth is caused

by anaerobic bacteria that proliferate in certain conditions. The mouth has plenty of

carbon dioxide, from exhaled breath, and water. The argument was if plants can utilize

the above two chemicals and produce carbohydrate and active oxygen, the same can

be achieved in the mouth if chlorophyll is introduced. However, it was soon found

that chlorophyll from toothpaste isolated in the mouth and as a part of a dynamic plant

system are two different things. Chlorophyll in toothpaste, however, did achieve

success as a pigment, though its stability was poor. This was solved by making copper

derivatives, such as copper chlorophyllin, which have a good stability.

The main raw materials for chlorophyll are the green leaves that plants produce in

quantity and are generally valued as food or feed.

Spinach

Spinach was probably ﬁ rst cultivated in Nepal, but the early history of the plant is in

the Indian subcontinent. India and Nepal are predominantly vegetarian regions, and

spinach, known locally as palak , is a valued food item. For this reason, spinach gener-

ally commands a good price. Spinach spread to China in the seventh century and to

the Arab world in the eleventh century. In the sixteenth century, the plant was intro-

duced to Italy, France, and other regions.

Spinach is rich in iron. This fact made the leaves very popular in the United States,

especially after the cartoon character “ Popeye ” popularized spinach as a food which

gives strength.

Plant Material

Spinach is an annual plant, though in very rare cases it can be biennial. It grows to a

height of 30 cm. The leaves are alternate, simple, and ovate or triangular. The size of

Green Leaves

i) Spinach: Spinacia oleracea L ( Amaranthacea )

ii) Alfalfa: Medicago sativa L ( Fabacea )

iii) Mulberry: Morus alba L ( Moraceae )

235

Natural Food Flavors and Colorants Mathew Attokaran