Attokaran M. Natural Food Flavors and Colorants

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316 Individual Flavors and Colorants

Identiﬁ cation Numbers

FEMA No. CAS US/CFR E - No.

Onion oil 2817

{

8002 - 72 - 0 182.20 –

8054 - 39 - 5

Onion extract/oleoresin – – 182.20 –

References

Abraham , K.O. ; Shankaranarayana , M.L. ; Raghavan , B. ; and Natarajan , C.P. 1976 . Alliums — varieties,

chemistry and analysis . Lebensm. - Wiss.Technol. 9 , 193 – 200 .

Arnault , Ingrid ; and Aunger , Jacques . 2006 . Seleno - compounds in garlic and onion . J. Chromatogr. A 1112

( 1 – 2 ), 23 – 30 .

Lombard , Kevin A. ; Geoffriau , Emmanuel ; and Pefﬂ ey , Ellen . 2002 . Flavonoid quantiﬁ cation in onion by

spectrophotometric and high performance liquid chromatography analysis . Hortscience 37 ( 4 ),

682 – 685 .

Mondy , N. ; Duplat , D. ; Christides , J.P. ; Arnault , I. ; and Auger , J. 2002 . Aroma analysis of fresh and pre-

served onions and leek by dual solid - phase microextraction - liquid extraction and gas chromatography -

mass spectrometry . J. Chromatogr. A 963 ( 1 – 2 ), 89 – 93 .

Takahashi , Mizuho ; and Shibamoto , Takayuki . 2008 . Chemical composition and antioxidant/anti - inﬂ am-

matory activities of steam distillate from freeze - dried onion ( Allium cepa L) sprout . J. Agric. Food Chem.

56 ( 22 ), 10462 – 10467 .

Zielinska , D. ; Nagels , L. ; and Piskula , M.K. 2008 . Determination of quercetin and its glycosides in onions

by electrochemical methods . Anal. Chim. Acta 617 ( 1 – 2 ), 22 – 31 .

Introduction

The sweet orange is believed to be a natural hybrid of pomelo ( Citrus maxima ) and

tangerine ( Citrus reticulata ). This orange originated in South Asia, probably in India

and Pakistan. It must also have grown in Southwest China and countries of what was

formerly Indochina. Although it was at one time a wild plant, it is now cultivated

commercially in different parts of the world. It is believed to have been introduced to

Europe in the sixteenth century by the Portuguese, who brought it either from India

or from Macao, an island near Hong Kong. Sweet orange, along with lemon, was

introduced to the Americas by Columbus during his second voyage. It thrived in the

West Indies and in Florida. Extension to California occurred in 1769 when the ﬁ rst

mission was established in San Diego. In Brazil, the Portuguese, and in other South

American countries, the Spanish, introduced the sweet orange. Before World War II,

the countries in which quantity of cultivation was highest, in descending order, were

the United States, Spain, Brazil, China, Japan, Italy, Palestine, North and South Africa,

Paraguay, and the West Indies (NIIR Board 2009 ).

Sweet orange is the most widely cultivated and used citrus fruit. Because of natural

hybridization and spread to different agro - climatic conditions, there are numerous

subvarieties. Along with the sweet orange, there is also bitter orange, classiﬁ ed as

Citrus aurantium .

The orange is relished both as a sweet fruit and a source of well - liked juice. Orange

juice, orange squash, and orange marmalade are popular processed items. All the same,

it is the oil in the peel that is valued as ﬂ avoring. Among all essential oils, orange oil

may perhaps occupy the number one position in quantity now produced.

Plant Material

Sweet orange is a trim evergreen tree with a rounded, generally uniformly spread

crown. The tree grows to a height of 6 – 9 m and the crown has a diameter of 4 – 6 m.

Its leaves are shiny and leathery, shaped oblong or elliptical. The length of the leaves

is about 10 cm. Leaves have petioles with a narrow wing. The orange blooms in spring,

and its ﬂ owers are white and grow in clusters. When the ﬂ owers appear, fruits from

the previous season may still be on the tree.

The orange, liked for its sweet and rich taste, is grown all round the world.

California produces varieties such as Navel and Valencia. In Brazil around 1820, a

Orange

Citrus sinensis L Osbeck ( Rutaceae )

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Natural Food Flavors and Colorants Mathew Attokaran

318 Individual Flavors and Colorants

single mutation produced the navel variety of orange. The mutation resulted in the

development of a second orange at the base of the original fruit. They appear to be

conjoined twins, but the outside appearance is like that of the human navel, hence the

name. Blood oranges are fruits with red streaks and whose juice has a dark color.

Scarlet navel is a variety with dual fruit mutations. Because the navel varieties are a

result of mutation, the fruits are seedless. Propagation is possible through grafts and

cuttings. Valencia is a variety that ripens late in the season and is extremely valuable

for juice.

Florida produces vast amounts of orange juice, leaving the peel to be used for

extraction of oil. French Guinea in Africa is another region that produces a great

quantity of sweet orange. The greatest increase in production occurred in the ﬁ rst half

of the twentieth century. Brazil had a long history of orange cultivation, beginning in

the sixteenth century. But it was only just before World War II that Brazil became a

major producer and exporter of the fruit, juice, and peel oil. Spain ’ s major area of

cultivation is a narrow land between Malaga and Castellon on the Mediterranean coast.

The Valencia variety is highly popular. An orange called Naranjito, meaning little

orange, wearing the colors of the Spanish team, was the ofﬁ cial mascot of 1982 soccer

World Cup held in Spain.

Palestine, with its ideal weather conditions, is a major producer of oranges. It is

reported that some trees there grow 2000 fruits per season. The Japanese industry

increased during World War II, when it was necessary for the country to be self -

sufﬁ cient. In India, oranges are quite popular, but extraction of oil by cold pressing

is done only by major juice processors.

Bitter orange is an evergreen tree with a glabrous trunk. It grows to a height of

10 m. It has long but far from sharp spines, and fragrant ﬂ owers. Its fruits are bitter

and sour.

Essential Oil

Essential oil in the orange rind is separated by puncturing the oil cells or by pressing,

during which both oil and juice come out. From this mixture, lighter oil can be sepa-

rated by centrifugation from the heavier aqueous phase. A substantial quantity of oil

is also distilled after the rind is separated from the edible inside.

In the United States, the earliest method of removing oil was to press the whole

fruit to obtain the juice and oil as an emulsion and then separate the two by centrifuge.

But this process has several disadvantages. Much of the oil gets trapped in the spongy

peel. Some oil hydrocarbons get trapped in the juice, causing quality variation in the

juice due to oxidative changes to the terpene hydrocarbons.

In recent times, highly sophisticated machines separate juice and pulp from the

washed and cut citrus fruits, leaving the peel for separation of oil. Some of the machines

developed are the Brown Automatic Citrus Fruit Juice Extractor and the FMC Whole

Fruit Extractor. After the juice and pulp are removed, the remaining peel is pressed

either between two rollers or by a tapering screw press, to remove all the oil through

cold pressing. The clean oil is separated from aqueous phase by centrifugation.

In many orange - growing regions, the collection of oil used to be done by hand -

operated processes such as the sponge method or the spoon scraping method. In the

80 Orange 319

sponge method, the pulp is removed manually from a cut fruit and the oil from the

peel is expressed by means of pressure exerted by hand. In French Guinea, the surface

of the fruit with peel is scraped with a sharp spoon and the oozing oil collected into

the spoon. In Japan, the fruits were cut into four pieces and the pulp removed by hand.

The peel was immersed in warm water and then pressed between two stainless steel

rollers moving at 20 – 30 revolutions per minute. This was then squeezed through

canvas bags to remove solid particles.

In Brazil and in European countries such as Spain and Italy, early extraction

methods were also hand - operated. Gradually, mechanization was introduced. This

included moving pins to puncture the cells, mechanical rotating spindles to scrape the

oil held in hand, and mechanical raspers to remove the ﬂ avedo from the whole fruit.

Today, sophisticated machines are used all over the world; Brazil is now the leader in

orange processing. The main products are the juice and the pulp; oil is a

by - product.

Only certain principles of extraction are described here. For more detail, readers

are advised to refer to specialized books on citrus processing.

Bitter orange peel contains essential oil, which is obtained by cold pressing. Leaves

and small twigs of this orange give on distillation orange petitgrain oil with a yield

of 0.2%. Freshly picked ﬂ owers of the orange tree, on steam distillation, produce

orange neroli oil. On poor storage of orange oils, the hydrocarbon limonene is oxi-

dized, giving a camphoraceous odor.

Terpeneless oil is produced by removing the terpene hydrocarbons such as limo-

nene. In this way, oxygenated terpenes, which give the ﬁ ne aroma and ﬂ avor, are

concentrated. At the same time, oxidizable limonene is removed. Deterpenation is

carried out by vacuum fractional distillation.

The main constituent of orange oil is limonene, which usually accounts for 90%

of the oil. The oil also contains aldehydes, coumarins, acids, esters, and other oxygen-

ated derivatives. Bitter orange oil also contains mainly limonene. In many respects,

the chemical composition is similar but for its bitter constituents. Some ﬂ avonoids

such as naringin and neohesperidin present in the peel are intensely bitter.

Volatile compounds and methyl esters of different oranges like blood orange, sweet

orange, and bitter orange have been analyzed (Mouﬁ da and Marzouk 2003 ). Limonene

is the most abundant constituent. Also identiﬁ ed were 18 fatty acids, mainly unsatu-

rated acids, in the juice.

Using dialysis/pervaporation system; ultraﬁ ltration/dialysis, and vacuum distilla-

tion, Auerbach (1995) has prepared folded orange oil. Limonene has been decreased

from 95.60% to 76.40%, while total oxygenated compounds have increased from

1.90% to 19.50%. While limonene is the dominant component of orange oil, Lawrence

(2009) has compiled recent investigations that detail the composition with respect to

minor components. Those who wish to study the composition of orange oil in detail

will do well to study this review.

Cold - pressed orange oil, according to the FCC, is an intensely yellow, orange, or

deep orange oil with the characteristic odor and ﬂ avor of the outer part of the sweet

orange fruit. It is miscible with dehydrated alcohol and with carbon disulﬁ de and

soluble in glacial acetic acid. The FCC allows the presence of antioxidants but recom-

mends not to use orange oil that contains a terebinthine odor.

320 Individual Flavors and Colorants

Physical characteristics recommended by the FCC are as follows.

Optical rotation + 94 ° to + 99 °

Refractive index 1.472 – 1.474 at 20 ° C

Speciﬁ c gravity 0.842 – 0.846

When a sufﬁ cient quantity of orange peel is accumulated, the peel is subjected to

steam distillation to produce distilled orange oil, which, according to the FCC, is a

colorless to pale yellow liquid with a mild citrus and ﬂ oral odor. It is soluble in most

ﬁ xed oils, in mineral oils, and in alcohol with haze. It is insoluble in glycerol and

propylene glycol but an antioxidant can be added.

Physical characteristics are as follows.

Optical rotation + 94 ° to + 99 °

Refractive index 1.471 – 1.474 at 20 ° C

Speciﬁ c gravity 0.840 – 0.844

Cold - pressed bitter orange oil, as per FCC description, is a pale yellow or yellow -

brown liquid with the characteristic aromatic odor of Seville orange and an aromatic

and bitter taste. It is miscible with absolute alcohol and an equal volume of glacial

acetic acid. It is soluble in ﬁ xed oils and in mineral oils. It is slightly soluble in pro-

pylene glycol and relatively insoluble in glycerol. It is affected by light and its alcohol

solutions are neutral to litmus. It may contain a suitable antioxidant.

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

Optical rotation + 88 ° to + 98 °

Refractive index 1.472 – 1.476 at 20 ° C

Speciﬁ c gravity 0.845 – 0.851

Uses

Orange oil may be one of the most widely used natural ﬂ avors. It is used in a wide

range of products such as confectionery, boiled sweets, cookies (especially in those

with cream), ice creams, dairy products, and even chocolate - based sweets. It has use

in orange - ﬂ avored soft drinks, popular worldwide. Another important use is as a ﬂ avor

booster in orange juice - and pulp - based food products such as juice, syrup, and

marmalade.

Bitter orange oil is also used in some of the above. In addition, it ﬁ nds use in

liqueurs, condiments, and relishes. Neroli and petitgrain oils are used as a lower priced

citrus ﬂ avor and also in cosmetics and toiletries.

Limonene, which comes out during deterpenation, is a starting material for the

manufacture of carvone, which is a ﬂ avoring chemical. Naringin and neohesperidin

are also used for making some artiﬁ cial sweeteners.

Orange oil also has anti - inﬂ ammatory and antimicrobial activities and is therefore

used in medicinal preparations. Orange oils including neroli and petitgrain oils are

also used as a ﬂ avor in some medicines.

80 Orange 321

Identiﬁ cation Numbers

FEMA No. CAS US/CFR E - No.

Orange oil, bitter, cold - pressed 2823 68916 - 04 - 1 182.20 –

72968 - 50 - 4

Orange oil, distilled 2821 68606 - 94 - 0 182.20 –

Orange oil, folded – 8028 - 48 - 6 182.20 –

Orange oil, sweet, cold - pressed 2825 8028 - 48 - 6 182.20 –

Orange oil, terpeneless 2822 8008 - 57 - 9 182.20 –

8028 - 48 - 6 –

Orange peel oil, sweet, terpeneless 2826 68606 - 94 - 0 182.20 –

94266 - 47 - 4

Orange terpenes 8028 - 48 - 6 182.20 –

Orange, terpenes, natural 68647 - 72 - 3 –

Orange water, bitter 72968 - 50 - 4 –

References

Auerbach , M.H. 1995 . A novel membrane process for folding essential oils . In C.T. Ho , C.T. Tan , and C.H.

Tong , eds., Flavor Technology: Physical Chemistry. Modiﬁ cations and Processes , ACS Syrup Series

610 . Washington, DC : American Chemical Society , pp. 127 – 138 (see Lawrence , Brian M. , Progress in

essential oils . Perfumer Flavorist , 2009 , 34 ( 1 ), 48 – 57 ).

Lawrence , Brian M. 2009 . Progress in essential oils . Perfumer Flavorist 34 ( 1 ), 48 – 57 ; ( 3 ), 52 – 56 .

Mouﬁ da , Saidani ; and Marzouk , Brahim . 2003 . Biochemical characterization of blood orange, sweet

orange, lemon, bergamot and bitter orange . Phytochemistry 62 ( 8 ), 1283 – 1289 .

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

pp. 70 – 113 .

Introduction

Oregano herb is more spicy after it is dried than when it is green and fresh. In ancient

Europe, medical men felt that the herb could cleanse the brain and give better vision.

It was also considered to be an antidote to the bite of poisonous spiders and

scorpions.

Oregano is widely used in Greek, Spanish, and Turkish cooking. Italians have been

using it in pizza for centuries. In early 1950s, due to the great mania for pizza all over

the world, the production and sale of oregano went up. In the southern Philippines,

oregano is used to mask the odor of beef, giving it a refreshing ﬂ avor.

Hippocrates, father of modern medicine, valued oregano as an antiseptic and cura-

tive for digestive and respiratory disorders.

Plant Material

Oregano belongs to the mint family. It is native to Mediterranean countries and nearby

Central Asian countries. Its close resemblance to marjoram leads to some confusion.

The plant is an erect perennial herb that grows to a height of 20 – 30 cm. It has tiny

leaves that contribute toward its pleasant pungent aroma. The stem is reddish,

the leaves greenish, ovate, and opposite. The color of the dried herb is pale

grayish - green.

Oregano contains some triglycerides, proteins, and minerals. But its most signiﬁ -

cant constituent is the essential oil, which gives the dried herb its aroma and ﬂ avor.

Essential Oil

The fresh herb gives an essential oil with a yield of 0.15 – 0.4%. As the oil is lighter

than water, distillation poses no special problems. Oil of oregano may be confused

with oil of sweet marjoram, but their great difference in optical rotation makes it easy

to identify them.

In various studies, an essential oil yield of 3 – 4% on a dry basis has been reported.

The principal components are carvacrol and thymol (Berghold et al. 2008 ; Stoilova

et al . 2008 ). Many other terpenes and a large amount of sesquiterpenes are also

reported.

Oregano

Origanum vulgare L ( Labiatae )

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324 Individual Flavors and Colorants

Spanish - type oregano oil, according to the FCC, is a yellowish - red to dark brownish -

red liquid having a pungent spicy aroma reminiscent of thyme. It is soluble in most

ﬁ xed oils and in propylene glycol. It is soluble with turbidity in mineral oil but is

insoluble in glycerin. Phenol content should be 60 – 75% by volume.

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

Optical rotation − 2 to + 3 °

Refractive index 1.506 – 1.512 at 20 ° C

Speciﬁ c gravity 0.935 – 0.960

Solubility 1 mL dissolves in 2 mL of 70% alcohol

Oleoresin

Powdered dry oregano herb, when extracted with hexane, gives an oleoresin with

3 – 4% yield. The volatile oil content of the product will be around 30% v/w.

Mediterranean oregano oleoresin is a dark greenish - brown viscous liquid with a

strong thyme - like odor and mildly bitter taste. Oleoresin in the case of oregano is

important, because of the large amount of sesquiterpenes that may not all distill with

steam. Additionally, it contains many valuable nonvolatile constituents, some of which

are antioxidants. The compounds reported are urosolic acid, oleanolic acid, protocat-

echnic acid, tilianin, sagittatoside, daucosterol, β - sistosterol, and stigmasterol (Wu

et al . 2000 ).

Uses

Oregano ﬂ avor is valued in European - style cooking. It goes well with sauces and

tomato preparations; in meat preparations and roasts made from pork, beef, lamb, veal,

chicken; cheese spreads; soups; in a wide range of vegetable preparations; and in all

kinds of pizza. Both oil and oleoresin are very convenient to use in processed versions

of the above foods.

Identiﬁ cation Numbers

FEMA No. CAS US/CFR E - No.

Oregano oleoresin/extract 2827 8007 - 11 - 2 –

84012 - 24 - 8 182.10

References

Berghold , H. ; Wagner , S. ; Mandl , M. ; Thaller , A. ; Muller , M. ; Rakowitz , M. ; Pasteiner , S. ; and Boechzelt ,

H. 2008 . Yield, content and composition of the essential oil of 5 oregano strains ( Origanum vulgare L)

depending on the developmental stage . Zeitschrift fuer Arznei Gewuerzpﬂ anzen 13 ( 1 ), 36 – 43 ( Chem.

Abstr. 149 :219356).

Stoilova , I. ; Bail , S. ; Buchbaur , G. ; Krastanov , A. ; Stoyanova , A. ; Schmidt , E. ; and Jirovetz , L. 2008 .

Chemical composition, olfactory evaluation and antioxidant effects of an essential oil of Origanum

vulgare L from Bosnia . Nat. Prod. Comm. 3 ( 7 ), 1043 – 1046 .

Wu , Rui ; Ye , Qi ; Chen , N. ; and Zhang , G. 2000 . Chemical constituents of Origanum vulgare L . Tianran

Chanwu Yanjiu Yu Kaifa 12 ( 6 ), 13 – 16 ( Chem. Abstr. 135 :2915).

Introduction

Paprika is a faintly pungent, brightly colored chili that is grown as an annual plant.

The same species produces the hot chili (red pepper). Chili is a gift of the New World

to the Old World. When Spanish explorers went to the Americas, they were fascinated

by the attractive, red - colored fruits. In colder climates of Europe, only brightly colored

and milder chilis, such as paprika, thrive, unlike in the hotter climate of Asia where

the strong and spicy varieties grow well.

Paprika is an important crop of Hungary and other neighboring Central and Eastern

European countries. High - grade paprika to be used as such is also produced in Spain,

Morocco, the United States, South Africa, and Israel. These are highly valued for their

color and ﬂ avor, and used in fresh, dried whole, or dried and powdered forms.

Extraction - grade paprika is lower priced and not so much valued for its appearance

other than its red color and typical ﬂ avor.

Paprika has gained importance through the discovery of its ascorbic acid (vitamin

C) content by the Hungarian scientist Albert Szent - Gyorgyi, for which he earned the

Nobel Prize in 1937. In fact, capsicum fruits have a higher content of ascorbic acid

than citrus fruits.

Plant Material

The plant is an annual herb with a woody stem with branches. A single white ﬂ ower

ends up becoming a fruit, which is initially green but becomes red when ripened.

There are different shapes, such as long and tapering with a length of 10 – 15 cm or

roundish and thick with a relatively ﬂ at end like that of a bell pepper. Hungarian

paprika is rich red in color with a shape that is tapering and pointed, while the Spanish

variety is less appealing in appearance with a roundish shape.

Spanish paprika was at one time an important raw material for oleoresin. The

Spanish extraction industry extended the raw material production to North African

countries such as Morocco. Paprika produced in Zimbabwe and South Africa domi-

nated the market for a while as a good raw material but has not made much progress

in recent years. Similarly, Mexico started in the oleoresin industry with raw material

grown locally, but the industry did not progress very well. The United States is a

Paprika

Capsicum annuum L ( Solanaceae )

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Natural Food Flavors and Colorants Mathew Attokaran