6983-79-5 Usage
Description
Bixin [CAS: 6983-79-5] (CI Natural Orange 4; CI 75120) is found in the seed of the plant Bixa orellana, native to India. Later it was found growing in South America, where the Indians used the red dye from the seeds as a body paint. An extract of the seeds appears on the market as annatto. This extract is used in coloring butter, margarine, and cheese such as Leicester cheese. In Mexican and South American cuisine, it finds special use as a flavor and coloring matter. Annato is available as an aqueous solution, as an oleaginous dispersion, and a spray-dried powder.
Chemical Properties
orange,purple lustrous crystalline solid plates
Occurrence
Bixin (CI Natural Orange 4; CI 75120) is found in the seed of the plant Bixa orellana, native to India. Later it was found growing in South America, where the Indians used the red dye from the seeds as a body paint. An extract of the seeds appears on the market as annatto. This extract is used in coloring butter, margarine, and cheese such as Leicester cheese. In Mexican and South American cuisine, it finds special use as a flavor and coloring matter. Annato is available as an aqueous solution, as an oleaginous dispersion, and a spray-dried powder.
Uses
Bixin is a carotenoid that is the main coloring component of annatto.
it is obtained from the bixa orellana tree. bixin is soluble in fats and
oils and the produced color is found in the fat fraction of the food.
it has a yellow hue, very good oxidation stability, fair light stability,
and good heat stability, but it is poor at very high temperatures,
such as above 125°c. one part bixin is equivalent to 1.5 parts caro-
tene. it is used at 0.5–10 ppm in finished foods, such as margarine,
salad dressings, popcorn oil, and baked goods. it is also termed
annatto extract. see annatto.
Definition
ChEBI: A carotenoic acid that is the 6'-monomethyl ester of 9'-cis-6,6'-diapocarotene-6,6'-dioic acid.
General Description
Bixin is a methyl ester of a dibasic fatty acid. On treating with alkali, it is hydrolyzed to form water soluble norbixin. It is obtained in pure form from annatto seeds. Bixin is a carotenoid and estimated as yolk and skin pigmenter.
Purification Methods
Crystallise bixin from Me2CO (violet prisms) [Pattenden et al. J Chem Soc (C) 235 1970]. [Beilstein 2 III 2020, 2 IV 2455, H 30 110.]
Check Digit Verification of cas no
The CAS Registry Mumber 6983-79-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,9,8 and 3 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 6983-79:
(6*6)+(5*9)+(4*8)+(3*3)+(2*7)+(1*9)=145
145 % 10 = 5
So 6983-79-5 is a valid CAS Registry Number.
InChI:InChI=1/C25H30O4/c1-20(12-7-13-22(3)16-9-17-25(28)29-5)10-6-11-21(2)14-8-15-23(4)18-19-24(26)27/h6-19H,1-5H3,(H,26,27)/b10-6-,13-7+,14-8-,17-9+,19-18-,20-12+,21-11+,22-16+,23-15-
6983-79-5Relevant articles and documents
Thermal degradation kinetics of bixin in an aqueous model system
Rios, Alessandro De O.,Borsarelli, Claudio D.,Mercadante, Adriana Z.
, p. 2307 - 2311 (2007/10/03)
The kinetics of the thermal degradation of the natural cis carotenoid bixin in a water/ethanol (8:2) solution was studied as a function of temperature (70-125°C), using high-performance liquid chromatography. The curves for the decay of bixin and formation of products (e.g., di-cis and all-trans isomers and a C17 degradation compound) did not adjust well to a first-order rate law, but very good fits were obtained using a biexponential model. This mathematical modeling gave the rate constant values for the formation of the primary products from bixin, and the energy barrier for each step was obtained. The di-cis isomers were formed immediately (15 kcal/mol) together with the decay of bixin, followed by a slow consumption, indicating their role as reaction intermediates. In fact, the di-cis isomers could easily revert to bixin (Ea ≈ 3 kcal/mol) or yield the primary C17 degradation product, with an energy barrier of 6.5 kcal/mol. In turn, 24 kcal/mol was necessary for the Bix - all-trans step, explaining its slower formation.
Synthesis of bixin and three minor carotenoids from annatto (Bixa orellana)
Haeberli, Adrian,Pfander, Hanspeter
, p. 696 - 706 (2007/10/03)
The three apocarotenoids methyl (9Z)-8'-oxo-6,8'-diapocaroten-6-oate (2), methyl (9Z)-10'-oxo-6,10'-diapocaroten-6-oate (4), and methyl (9Z)-14'- oxo-6,14'-diapocaroten-6-oate (5), recently isolated from annatto, were synthesized. The key step of all three syntheses was the Wittig reaction of the (Z)-terminus 6 with the phosphonium salts 15, 18, and 24, carrying the polyene chain. Bixin (1) was synthesized from 2 in a Horner-Emmons reaction.
