Bixinis anapocarotenoidfound in the seeds of theachiote tree(Bixa orellana)[2]from which it derives its name. It is commonly extracted from the seeds to formannatto,a naturalfood coloring,containing about 5% pigments of which 70–80% are bixin.[3]
| |
| Names | |
|---|---|
| IUPAC name
(2E,4E,6E,8E,10E,12E,14E,16Z,18E)-20-Methoxy-4,8,13,17-tetramethyl-20-oxoicosa-2,4,6,8,10,12,14,16,18-nonaenoic acid
| |
| Other names
cis-Bixin; α-Bixin; 9-cis-6,6'-Diapo-ψ,ψ-carotenedioic acid, 6-methyl ester
| |
| Identifiers | |
| |
3D model (JSmol)
|
|
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.027.499 |
PubChemCID
|
|
| UNII |
|
CompTox Dashboard(EPA)
|
|
| |
| |
| Properties | |
| C25H30O4 | |
| Molar mass | 394.511g·mol−1 |
| Appearance | Orange crystals |
| Melting point | 198 °C (cis-isomer) 217 °C (trans-isomer) |
| Insoluble | |
| Hazards | |
| NFPA 704(fire diamond) | |
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).
| |
Applications
edit
Red seeds of the achiote tree 
Bixin is one of the colorants used in the snack Cheetos.
Several thousand tons are harvested annually.[4]
Chemical properties
editBixin is unstable. Itisomerizesintotrans-bixin (β-bixin), thedouble-bond isomer.[1]
Chemical structure oftrans-bixin
Bixin is soluble in fats andalcoholsbut insoluble in water. Upon exposure toalkali,themethylesterishydrolyzedto produce thedicarboxylic acidnorbixin,a water-soluble derivative.
Chemical structure of norbixin
References
edit- ^abMerck Index,11th Edition,1320
- ^Bouvier, Florence; Dogbo, Odette; Camara, Bilal (2003)."Biosynthesis of the Food and Cosmetic Plant Pigment Bixin (Annatto)".Science.300(5628): 2089–2091.Bibcode:2003Sci...300.2089B.doi:10.1126/science.1085162.ISSN0036-8075.JSTOR3834418.PMID12829782.S2CID560600.
- ^Executive Summary BixinArchivedJuly 21, 2011, at theWayback Machine,National Toxicology Program
- ^Stringheta, Paulo C.; Silva, Pollyanna I.; Costa, André G.V. (2018). "Annatto/Urucum— Bixa orellana".Exotic Fruits.pp. 23–30.doi:10.1016/B978-0-12-803138-4.00006-X.ISBN9780128031384.