Bixin from Bixa orellana

Synonyms Achiote Annatto extract Annatto tree extract Annotta extract Arnotta extract Bixa orellana BIxIn Cl 75120 Natural orange 4 Definition Carotenoid color contg. bixin (oll/fat extract) or norbixin (alkaline aq. extract), derived from Bixa oreiiana Properties Yel.-red sol ns. or powd. 

Bixin is the main pigment of annato extract. Annato originates from the West Indies and the pigment is isolated from the seed pulp of the tropical bush Bixa orellana, Bixin is the monomethyl ester of norbixin, a dicarboxylic acid homologous to crocetin. 

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. 

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. 

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. 

Haberli, A., and Pfander, H., Synthesis of bixin and three minor carotenoids from Annatto (Bixa Orellana), Helv. Chim. Acta, 82, 696, 1999. 

Amongst the apocarotenoids with less than 40 carbon atoms in the skeleton there are several examples of naturally occurring carotenoid mono- and dicarboxylic acids [7]. These include crocetin (31) from saffron, bixin (32) from Bixa orellana, azafrin (33) from roots of Escobedria scabrifolia and neurosporaxanthin (4) from yeasts (Neuro-spora sp.), Fig. 13. 

Bixin, present in Annatto, is an important natural colourant which is obtained commercially from Bixa orellana. It is unusual in not having a typical isoprenoid structure composed of multiples of the fundamental C5 unit. All trans diethyl norbixin has been synthesised readily from crocetindial (ref.55,p221) by the Wittig reaction with two moles of the phosphoran from the triphenylphosphonium salt of ethyl chloracetate as shown in Scheme 20. The natural product is the form in which the colourant is used. 

C25H30O4, Mr 394.51, orange to purple-colored plates, mp. 217 °C. The more labile (9Z) form (a-bixin, bixin) of the carotinoid B. is contained in ripe seeds of the tropical annatto tree (roucou) Bixa orellana (Bixa-ceae). The crude concentrate is known as annatto (or-lean) and is used to color foods (E 160b), e. g., margarines and cheeses as well as cosmetics. lit. Beilstein EIV 2,2355 Britten et al.. Carotenoids, Basel Birkhauser 1995 Helv. Chim. Acta 82, 696 (1999) (synthesis) Merck-Index (12.), No. 1347 Phytochemistry 46,1379 (1997) (carotinoids from annatto) Zechmeister 18,320-330. - [HS 320300 CAS 6983-79-5 (a-B.) 39937-23-0 (p-B.)l... 

Annato is a yellow oil or aqueous alkaline extract of fruit pulp of Raku or Orleans shrubs or brushwood Bixa orellana). The major pigments of annato are bixin (XVIII) and norbixin, both of which give dicarboxylic acids upon hydrolysis. Oleoresin from paprika is a red, oil extract containing about 50 different pigments. The aqueous extract of saffron (more accurately, from the pistils of the flower Crocus sativus) contains crocin (XVII) as its main constituent. It is used for coloring beverages and bakery products. 

Bixin (328) is one of a number of deeply colored carotenoid degradation materials that can be isolated from the pericarp of the fruit of the tree Bixa orellana. Extracts, known as Annatto, are used as yellow food colors E 160(b). Other components include the trans isomer and nor-bixin. The extraction and chemistry of Annatto has been reviewed by... 

Anetto, derived from Bixa orellana (India, South America), is used in food coloring and contains Bixin as main compoimd. 

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