Attokaran M. Natural Food Flavors and Colorants

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56 Individual Flavors and Colorants

Uses

Allspice ﬂ avor is very important in Caribbean cooking. It is used in sausages and other

meat products. Its ﬂ avor is well liked in sauces and in pickling. In the Middle East,

the ﬂ avor is also popular. It is used in American desserts and European sausages. When

included in processed food, pimenta oil and oleoresin are very convenient to use.

Generally, oleoresin gives a fuller and rounded ﬂ avor compared with essential oil.

Having a reasonable amount of eugenol, it has some antimicrobial and deodorant

properties. However, for these uses, clove extractive will be more appropriate.

Allspice Leaf Oil

Allspice leaves on drying give an essential oil with a yield of 0.7 – 2.9%. The ﬂ avor

of this oil is considered inferior. Leaf oil has a pale yellow to brownish - yellow color.

Its main constituent is eugenol, which is present to an extent of 65 – 95%.

Leaf oil of Pimenta dioica shows eugenol (76.02%) as the main constituent. Other

compounds include methyl eugenol and β - caryophyllene (Jirovetz et al. 2007a ).

Pimenta racemosa leaf oil exhibits eugenol (45.60%), myrcene (24.97%), and chavi-

col (9.31%) (Jirovetz et al. 2007b ).

Pimenta leaf oil, according to the FCC, is a pale yellow to light brown - yellow

liquid when freshly distilled, which becomes darker with age. In contact with iron, it

acquires a blue shade, turning dark brown. It is soluble in propylene glycol and is

soluble with slight opalescence in most ﬁ xed oils. It is relatively insoluble in glycerin

and in mineral oil.

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

Optical rotation − 2 ° to + 0.5 °

Refractive index 1.531 – 1.536 at 20 ° C

Speciﬁ c gravity 1.037 – 1.050

Solubility 1 mL dissolves in 2 mL of 70% alcohol, a slight

opalescence may occur when additional solvent is added

Allspice leaf oil is also used for the ﬂ avoring of food items such as ice cream,

confectionary, chewing gum, baked goods, beverages, and medical preparations. The

leaf oil generally is cheaper than the berry oil.

Identiﬁ cation Numbers

FEMA No. CAS US/CFR E - No.

Pimenta berry oil 2018 8006 - 77 - 7 182.20 –

Pimenta leaf oil 2901 8006 - 77 - 7 182.20 –

Pimenta oleoresin/extract 2019 8006 - 77 - 7 182.20 –

84929 - 57 - 7 –

14 Allspice (Pimenta) 57

References

Jirovetz , L. ; Buchbauer , G. ; Stoilova , I. ; Krastanov , A. ; Stoyanova , A. ; and Schmidt , E. 2007a . Spice plants:

chemical composition and antioxidant properties of Pimenta. Lindl essential oil. Part 1: Pimenta dioica

(L) Merr. Leaf oil . Ernaehrung (Vienna) 31 ( 2 ), 55 – 62 (English).

Jirovetz , L. ; Buchbauer , G. ; Stoilova , I. ; Krastanov , A. ; Stoyanova , A. ; Schmidt , E. 2007b . Spice plants:

chemical composition and antioxidant properties of Pimenta Lindl. essential oil. Part 2: Pimenta race-

mosa (Mill) J.W. Moore leaf oil of Jamaica . Ernaehrung (Vienna) 31 ( 7/8 ), 293 – 300 (English).

Lawrence , Brian M. 2006 . Progress in essential oils . Perfumer Flavorist 31 ( 5 ), 52 – 62 .

Introduction

Anka red natural pigment is produced from Monascus fungus, known in Japan as koji

fungus. A Chinese medical book ﬁ rst mentioned the pigment as “ ang - kak ” or “ red

mold rice, ” which has been used since 1884. Philippe van Thieghem later isolated and

named the mold Monascus ruber . In 1895, mold from red mold rice was obtained in

Indonesia. The fungus was named Monascus purpureus . After this, several species

were studied and isolated.

Red mold rice is produced in Southern China, Japan, and Southeast Asia, using the

traditional Koji process. There have been several modiﬁ cations and more than 50

patents are registered. The pigments used as traditional natural food color in China

and Japan are a mixture of yellow (monascin, anka ﬂ avin), orange - red (rubropunctatin,

monascorubrin), and red - purple (rubropunctamine, monascorubramine) compounds

(Chiu and Poon 1993 ).

Microbial Material

Monascus fungus grows in substrates that contain plenty of carbohydrates (Delgado -

Varghas and Paredes - Lopez 2003 ). In the Koji process, substrates such as rice, wheat,

soybeans, or corn are inoculated. The major fungus used in Asia is M. purpureus . The

ﬁ rst stage is a solid state but may be continued at a later stage using submerged culture

(Chiu and Poon 1993 ).

In pigment production, the fungus produces an antibiotic, monascidin A, which is

unwelcome in a food product. Improvements in strains and process have avoided this

defect. Regulation of oxygen and carbon dioxide during the process has yielded higher

efﬁ ciency for production (Delgado - Varghas and Paredes - Lopez 2003 ).

Extractive

The traditionally produced red color is poorly soluble in water but soluble in alcohol.

The color is sensitive to light. At lower acid pH, the color is more orange, while at

higher pH it is purplish red.

Water - soluble red pigments are produced by reacting extracted pigments with

amino acetic acid and amino benzoic acid (Wong and Koehler 1983 ). The modiﬁ cation

gives the same characteristics as those obtained with glutamic acid or gelatin. The red

Anka - Red Fungus

Monascus anka or M. purpureus

Natural Food Flavors and Colorants Mathew Attokaran

60 Individual Flavors and Colorants

pigments can be dissolved in ethanol and propylene glycol and freeze - dried for use

as a food color. Use of complex culture media containing glucose or sucrose, corn

steep liquor, and monosodium glutamate results in better production of the red pigment

than with semisynthetic medium (Hamano and Kilikian 2006 ).

Use

The pigment can be used in processed meat, fruit products, various sauces, and ice

cream. The Monascus pigments are not approved for use in the United States. The

European Commission has not yet assigned it an E - number. It would appear that this

pigment is more often used in Asia but is becoming less and less important as other

natural dyes such as paprika and annatto become more popular.

References

Chiu , Sil - Wai ; and Poon , Yam - Kau . 1993 . Submerged production of Monascus pigments . Mycologia 85

( 2 ), 214 – 218 .

Delgado - Varghas , Franscisco ; and Paredes - Lopez , Octivio . 2003 . Natural Colorant for Food and

Nutraceutical Uses . Boca Raton, FL : CRC Press , pp. 221 – 255 .

Hamano , P.S. ; and Kilikian , B.V. 2006 . Production of red pigments by Monascus ruber in culture media

containing corn steep liquor . Braz. J. Chem. Eng . 23 ( 4 ), 1 – 7 .

Wong , Hin - Chung ; and Koehler , Philip E. 1983 . Production of red water - soluble Monascus pigments .

J. Food Sci. 48 , 186 – 189 .

Introduction

Aniseed (anise seed) has been known to mankind for a long time, reported to have

been found in Egypt more than 1000 years before Christ. Its aroma was believed to

prevent bad dreams while sleeping. In the past, it was believed to increase sexual

feeling and the ﬂ ow of milk. Among the many beneﬁ cial effects attributed to aniseed

is its ability to cure insect bites, control mites and lice, be a good bait for rodents, and

have some medicinal effect: It is particularly effective for preventing gas and discom-

fort due to overeating, for preventing bad breath, and for use as a diuretic.

There have been conﬂ icting reports of the seed being taxed and encouragement by

government bodies to propagate the crop. All these point to the importance of the

seed. In India, aniseed is often confused with other similar seeds like fennel, which

also has digestion - improving qualities. Its ﬂ avor is similar to that of star anise, but

the two are botanically quite different.

Plant Material

Aniseed, which belongs to the ajowan family, is native to the Mediterranean region,

especially Egypt, Greece, Turkey, and Lebanon. In recent times, its cultivation has

extended to many countries. They include American nations such as Argentina, Chile,

the United States, and Mexico; Mediterranean countries such as Cyprus, Spain, and

Syria; Asian nations such as China, India, and Pakistan; and the island of Madagascar.

The United States is a net importer.

The plant is an herbaceous annual that grows to about 1 m in height. It has long

stalked leaves at the base and short stalked leaves at the top. The seeds have a

yellowish - gray to yellowish - brown color. It is oval in shape with a length of 3 – 5 mm.

The seed has longitudinal ridges, usually with a bit of thin stalk attached. It has a

sweet aroma and ﬂ avor, reminiscent of licorice, and can be pleasant to chew.

Chemistry

The chemical composition may vary slightly among seeds grown in different places.

Generally, on dry basis, it has protein 18%, ﬁ xed oil 8 – 23%, total sugar 3.5%, starch

5%, crude ﬁ ber 12 – 25%, and essential oil 2 – 7%. The major component of volatile oil

is anethole (Fig. 16.1 ).

Aniseed

Pimpinella anisum L ( Umbellifereae )

Natural Food Flavors and Colorants Mathew Attokaran

62 Individual Flavors and Colorants

Essential Oil

An average quality dry seed, on crushing and steam distillation, gives about 2 – 3%

volatile oil. Anethole accounts for 80 – 90%, which gives the characteristic ﬂ avor. Star

anise also has a high anethole content. The quantity of aniseed oil produced worldwide

is only a fraction of volatile oil from star anise . Other components from aniseed

include α - pinene, camphene, linalool, anisaldehyde, acetoanisole, and safrole.

Aniseed oil has rich aromatic odor and ﬂ avor and can be considered to be slightly

more pleasant than the oil of star anise. According to the FCC, anise oil occurs as a

pale yellow liquid with the characteristic odor and taste of anise.

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

Optical rotation − 2 to + 1

Refractive index 1.553 – 1.560

Speciﬁ c gravity 0.978 – 0.988

Solubility 1 mL dissolves in 3 mL 90% alcohol

Uses

Aniseed oil is well suited for ﬂ avoring various processed meat preparations of Europe.

It is particularly well liked in Italian dishes, including sausages. It is also used in

alcoholic liquors and liqueurs. It has many medicinal properties and is useful in

mouthwashes, digestive, and antiseptic preparations. There are unconﬁ rmed reports

of its use in aromatherapy and for perfumery.

Anethole separated from the oil has many uses; it can be added to give ﬂ avor to

foods and beverages. Anethole is reported to have the property of spontaneous forma-

tion of microemulsion, which gives alcoholic beverages their cloudy appearance. This

has potential for use in many beverages and pharmaceutical preparations.

Anethole has antinemetode, antimicrobial, and anti - insect properties.

Identiﬁ cation Numbers

FEMA No. CAS US/CFR E - No.

Anise oil 2094 84775 - 42 - 8 182.20 –

Anise oleoresin – 84775 - 42 - 8 – –

Figure 16.1. Anethole.

Introduction

Annatto is used both as a spice and as a coloring material. The plant can be described

as a bush. The Mayans of Central America used the dye as war paint. It was known

to Latin Americans as achiote . Writers of the nineteenth century have gloriﬁ ed it as

having the “ color of ﬁ re. ” Presently, it is used on cosmetics and food.

Plant Material

Annatto is the bright yellow - red to red pigment in the aril (seed coat) of an evergreen

shrub growing on the fringes of forests in a wide range of tropical countries. The plant

has heart - shaped leaves, generally with red - colored veins. It was used as a hedge plant

in the gardens of colonial era because of its pink ﬂ owers. The fruit capsule is heart -

shaped with opposing clefts and reddish - brown prickly spines. When the pods are

ripe, it splits open into halves. Inside, 40 – 50 seeds are covered in a red pulpy skin.

The seed is conically shaped with a rough four - sided bottom and appears red because

of aril. The red pigments are in the seed coat and not in the inside kernel. The seed

coat containing the pigment sometimes separates from the seed on abrasion after

steaming.

The seed capsules appear about 30 days after ﬂ owering and ripen during the next

1 – 2 months (Satyanarayana et al . 2003 ). The color changes from green to red.

Harvesting is best done when the seeds split open. This prevents damage in case of

rain and prevents scattering of the seeds. The cluster of ripe capsules is cut at the ﬁ rst

node. Under normal conditions, the ﬁ rst harvest can be obtained 18 months after

planting. The average yield of seed from a hectare is 300 – 600 kg and in exceptionally

good circumstances 750 – 900 kg. Photo 2 shows unopened and opened annatto pods.

It grows in many countries of South America, Peru being the leading one. It is also

grown in Bolivia, Brazil, Ecuador, Guyana, Jamaica, and Suriname. The crop also

occurs in lesser amounts in Africa, in Angola, Kenya, Nigeria, and Tanzania.

Annatto is also found in the Asian countries of India, the Philippines, Thailand,

and Vietnam. In most places, the shrub grows wild. According to an estimate of the

1990s, the total dry seeds traded in the world are believed to be in excess of 10,000 mt.

A large percentage of these are used for extraction of natural colors. The extraction

and chemistry of the pigments have been studied by Preston and Rickard ( 1980 ).

Annatto

Bixa orellana L ( Bixaceae )

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64 Individual Flavors and Colorants

Chemistry

The principal coloring compound of annatto is bixin (Fig. 17.1 ), which is a diapoca-

rotenoid. The numbering of carbon atoms is as in regular carotenes as if carbon rings

are at both ends, with middle carbons given 15 and 15 ′ . Carotenoids like β - carotene

have two rings and therefore have 40 carbon atoms. Bixin is therefore a unique C25

carotenoid.

Figure 17.1. Bixin.

HOOC 9'

COOCH

Photo 2. (A) Unopened annatto pods. (B) Opened pods with seeds inside. See color

insert.

17 Annatto 65

Natural bixin is cis in 9 ′ positions with one of the carboxylic acid esteriﬁ ed to

methyl group. While the above is orange with melting point of 198 ° C, all trans - bixin

has a reddish color and a melting point of 216 – 217 ° C. This isomerization can be

partially effected by heat. It can also be achieved by the action of iodine in benzene,

but naturally this is not an option for food use. cis - Bixin is only weakly soluble in fat.

It is soluble in most polar organic solvents.

Saponiﬁ cation of bixin extract with warm (less than 70 ° C) 5% aqueous potassium

hydroxide (KOH) or sodium hydroxide will yield corresponding potassium or sodium

derivative of cis - nor - bixin (Fig. 17.2 ) . nor - Bixin is isomeric to all trans pigment,

crocetin, which can be derived from the yellow pigment crocin, which is present in

saffron.

The color shade and absorption characteristics of the pigments bixin and nor - bixin

are presented in Table 17.1 (Satyanarayana et al. 2003 ).

Extraction

Dry seed without grinding is fed into a percolator and extracted by gravity percolation

at ambient conditions using acetone. Alternatively, an improved extraction can be

obtained as follows. An initial wash with n - hexane will remove all the fatty impurities

Figure 17.2. nor - Bixin.

HCOO

COOH

Table 17.1. Properties of coloring compounds of annatto

Physical Properties UV - VIS Spectrophotometric Analysis

Compound Physical

Description

MP ( ° C) Solvent

Used

Wavelength

Maxima

Extinction

Coefﬁ cient (E

1 cm

)

cis - Bixin Red - brown

crystalline

189.5 – 190.5 Chloroform 501,470 2880,3230

trans - Bixin Red - mauve

crystalline

204 – 206.8 Chloroform 507,476 2970,3240

cis - nor -

Bixin

Orange - red

needles

Charred at 290

and did not

melt < 300

0.1 M NaOH 482,453 2550,2850

trans - nor -

Bixin

Dark red - black

granular

Darkened at 250

and did not

melt < 325

0.1 M NaOH 486,457 n.d.

UV - VIS = ultraviolet-visible; n.d. = not determined owing to very low solubility.