Carotenoids annatto

Saffron is a spice that is used sometimes for flavor, but mostly for the yellow color it imparts to foods. Because of its expense, saffron is often replaced in recipes by another carotenoid, annatto, or the unrelated dye molecule in turmeric. Like the other carotenoid dyes, saffron is an antioxidant, but its expense makes it unsuitable as a preservative or dietary supplement. 

Caramel Carotenoids Annatto (bixin) Canthaxanthin (3-apocarotenal Chlorophylls Riboflavin Others... 

Annatto is classified as El 60(b). It is extracted from the seeds of the tree Bixa orellana which grows in America, India and East Africa. The extract is a mixture of two pigments, bixin and nor-bixin. Bixin is oil soluble, whereas nor-bixin is water soluble (it is one of the two water soluble carotenes - the other is crocin), and both of the pigments are diapo-carotenoids. Annatto has long been used as a food colouring and also has some uses as a food flavouring. 

The chief coloring principle found ia the oil or fat extracts of annatto seeds is the carotenoid hixin (36, R = UH3) (Cl Natural Orange 4, Cl No. 

Annatto is a colored pigment that is extracted from the Central and South American plant Bixa orellana. The color comes from the resinous outer covering of the seeds of the plant, which is composed of the carotenoid pigments bixin and norbixin and their esters. The central portion of those molecules is the same as that of the molecule beta-carotene, and the yellow-orange color of annatto comes from the same physical chemistry origins as the orange color of beta-carotene. 

Beta-carotene is used in foods to provide color (margarine would look as white as vegetable shortening without it). Another similar molecule, annatto, is used in cheeses. Another famous carotenoid dye, saffron, is used to color rice and other foods. 

Spices snch as paprika, saffron, and annatto, which are traditionally employed in different parts of the world, contain nniqne carotenoids. Fignre 4.2.2 shows the strnctnres of these carotenoids. 

FIGURE 4.2.2 Structures of carotenoids found in paprika (capsanthin and capsombin), saffron and gardenia (crocetin derivatives), and annatto (bixin and norbixin). 

Bixin, a diapocarotenoid with a cis configuration at the carbon 9 and two carboxylic groups (one methylated), accounts for more than 80% of the total carotenoid content in annatto seeds, and has only been encountered to date in these seeds. The amount of red pigments in annatto seeds varies from 1.5 to 4%, depending on the variety. Bixin is the main pigment in commercial annatto powder... 

Mercadante, A.Z. and Pfander, H., Carotenoids from annatto a review, Recent Res. Devel. Agric. Food Chem., 2, 79, 1998. 

Mercadante, A.Z., Composition of carotenoids from annatto, in Chemistry and Physiology of Selected Food Colorants, Ames, J.M. and Hofmann, T.E., Eds., ACS Symposium Series 775, Washington, 2001, chap. 6. 

Scotter, M.J., Characterization of the coloured thermal degradation products of bixin from annatto and a revised mechanism for their formation, Food Chem., 53, 111, 1995. Zechmeister, L., Cis-trans isomerization and stereochemistry of carotenoids and diphenylpolyenes, Chem. Rev., 34, 267, 1944. 

Colorant containing annatto and Ca caseinate as carrier mixed with water to be added directly to cheese milk yielding uniform colored cheese mass Water-dispersible beadlet of p-carotene is mixed with oil to attein composition that remains stable even in presence of polyphosphates and with antioxidant action even in absence of ascorbic acid Blending carotenoid pigment and soybean fiber (wifii tomato juice) as effective ingredient for dispersion stability... 

However, several hours of measurement are typically needed to achieve good signal-to-noise and high resolution, especially for 2D techniques. Other 2D techniques were used for structure elucidation of carotenoids from guava and annatto seeds. ... 

Mercadante, A.Z., Steck, A., and Pfander, H., Isolation and structure elucidation of minor carotenoids from annatto (Bixa orellana L.) seeds. Phytochemistry, 46, 1379, 1997. 

Detailed information about carotenoids found in food or extracted from food and evaluated for their potential as food colorants appeared in Sections 4.2 and 6.2. We would like to mention some new data about the utilization of pure carotenoid molecules or extracts as allowed food additives. Looking to the list of E-coded natural colorants (Table 7.2.1), we can identify standardized colorants E160a through f, E 161a, and E161b as natural or semi-synthetic derivatives of carotenoids provided from carrots, annatto, tomatoes, paprika, and marigold. In addition, the extracts (powders or oleoresins) of saffron, - paprika, and marigold are considered more economical variants in the United States and European Union. 

Chen G and Djuric Z. 2001. Carotenoids are degraded by free radicals but do not affect lipid peroxidation in unilamellar liposomes under different oxygen tensions. FEBS Letters 505(1) 151-154. colorMaker, Inc. Anaheim, CA, http //www.colormaker.com/CM/AboutNC/annatto.asp. 

FIGURE 12.5 Structures of bixin and norbixin, cis carotenoids from annatto. 

Natural colours include annatto, anthocyanins, beetroot red (betalaines), caramel, carotenoids, cochineal and lac pigments, flavanoids, chlorophylls and tumeric. There is a trend towards encapsulating natural colours for food use, but this is not yet reflected in the extraction techniques described in the published analytical methods. Lancaster and Lawrence (1996) described the extraction and... 

ANNATTO FOOD COLORS. These colors are natural carotenoid colorants derived from the seed of the tropical annatto tree (Bixa nrellana). The surface of the seeds contains a highly colored resin, consisting primarily of the carotenoid bixin. The bixin is extracted from the seed by a special process to produce a pure, soluble colorant. Bixin, one of the relatively few naturally occurring cts compounds, has a chemical structure similar to the nucleus of carotene with a free and esterified carboxyl group as end groups. Its formula is CM LoCL. (See Fig. I). 

Bixin is an oil soluble, highly stable coloring ingredient. The saponification of the methyl ester group to form the dicarboxylic acid yields the water-soluble form of bixin, sometimes called norbixin. Annatto colorants date back into antiquity. The colorant has been used for centuries in connection with various textiles, medicinals, cosmetics, and foods. Annatto colors have also been used to color cheese, butter, and other dairy products for over a century. See also Carotenoids. 

See also Annatto Food Colors Carotenoids Chlorophylls Colorants (Foods) and Photosynthesis. 

Annatto Extracts occur as dark red solutions, emulsions, or suspensions in water or oil or as dark red powders. The extract is prepared from annatto seed, Bixa orellana L. (Fam. Bixa-ceae), using a food-grade extraction solvent. Bixin is the principal pigment of oil-soluble Annatto Extracts. Norbixin is the principal pigment of alkaline water-soluble Annatto Extracts. Commercial preparations are usually mixtures of bixin, norbixin, and other carotenoids. 

Margarine is colored with carotenoids, and synthetic p-carotene is by far the most widely used. Carotene dissolves very slowly in oil. Therefore, the compound is pulverized to a particle size of 2-5 pm and the microcrystals are suspended in oil to retard oxidation (228). Natural extracts containing carotenoids, for example, annatto (bixin), carrot oil, and red palm oil also have been used. Annatto, which is used in butter, is somewhat sensitive to light and may have an orange or slightly pink hue, particularly when the aqueous phase is acid (4). Mixtures of annatto and turmeric extracts result in a more typical color than annatto alone (229). Many margarine manufacturers purchase blends of colors and vitamins customized for their specific products. 

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