Bixin: Difference between revisions
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'''Bixin''' is an [[apocarotenoid]] found in the seeds of the [[Bixa orellana|achiote tree]] (''Bixa orellana'')<ref>{{Cite journal|last1=Bouvier|first1=Florence|last2=Dogbo|first2=Odette|last3=Camara|first3=Bilal|date=2003|title=Biosynthesis of the Food and Cosmetic Plant Pigment Bixin (Annatto)|url=https://www.jstor.org/stable/3834418|journal=Science|volume=300|issue=5628|pages=2089–2091|doi=10.1126/science.1085162 |jstor=3834418 |pmid=12829782 |s2cid=560600 |issn=0036-8075}}</ref> from which it derives its name. It is commonly extracted from the seeds to form [[annatto]], a natural [[food coloring]], containing about 5% pigments of which |
'''Bixin''' is an [[apocarotenoid]] found in the seeds of the [[Bixa orellana|achiote tree]] (''Bixa orellana'')<ref>{{Cite journal|last1=Bouvier|first1=Florence|last2=Dogbo|first2=Odette|last3=Camara|first3=Bilal|date=2003|title=Biosynthesis of the Food and Cosmetic Plant Pigment Bixin (Annatto)|url=https://www.jstor.org/stable/3834418|journal=Science|volume=300|issue=5628|pages=2089–2091|doi=10.1126/science.1085162 |jstor=3834418 |pmid=12829782 |bibcode=2003Sci...300.2089B |s2cid=560600 |issn=0036-8075}}</ref> from which it derives its name. It is commonly extracted from the seeds to form [[annatto]], a natural [[food coloring]], containing about 5% pigments, of which 70–80% are bixin.<ref>[https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/bixin_508.pdf Executive Summary Bixin] {{webarchive |url=https://web.archive.org/web/20110721055506/http://ntp-server.niehs.nih.gov/?objectid=F59ACAC5-F1F6-975E-7C563568F5F7351B#selection |date=July 21, 2011 }}, National Toxicology Program</ref> |
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==Applications== |
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:[[file:CheetosCrop.jpg|thumb|Bixin is one of the colorants used in the snack Cheetos.]] |
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Several thousand tons are harvested annually.<ref>{{cite book |doi=10.1016/B978-0-12-803138-4.00006-X|chapter=Annatto/Urucum— Bixa orellana |title=Exotic Fruits |year=2018 |last1=Stringheta |first1=Paulo C. |last2=Silva |first2=Pollyanna I. |last3=Costa |first3=André G.V. |pages=23–30 |isbn=9780128031384 }}</ref> |
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==Chemical properties== |
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:[[File:Trans-bixin.png|thumb|center|320px|Chemical structure of ''trans''-bixin]] |
:[[File:Trans-bixin.png|thumb|center|320px|Chemical structure of ''trans''-bixin]] |
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Latest revision as of 21:36, 6 December 2024
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| Names | |
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| 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
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| Other names
cis-Bixin; α-Bixin; 9-cis-6,6'-Diapo-ψ,ψ-carotenedioic acid, 6-methyl ester
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| Identifiers | |
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3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.027.499 |
PubChem CID
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| UNII |
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CompTox Dashboard (EPA)
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| Properties | |
| C25H30O4 | |
| Molar mass | 394.511 g·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 their standard state (at 25 °C [77 °F], 100 kPa).
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Bixin is an apocarotenoid found in the seeds of the achiote tree (Bixa orellana)[2] from which it derives its name. It is commonly extracted from the seeds to form annatto, a natural food coloring, containing about 5% pigments, of which 70–80% are bixin.[3]
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
[edit]Bixin is unstable. It isomerizes into trans-bixin (β-bixin), the double-bond isomer.[1]
Chemical structure of trans-bixin
Bixin is soluble in fats and alcohols but insoluble in water. Upon exposure to alkali, the methyl ester is hydrolyzed to produce the dicarboxylic acid norbixin, a water-soluble derivative.
Chemical structure of norbixin
References
[edit]- ^ a b Merck 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. ISSN 0036-8075. JSTOR 3834418. PMID 12829782. S2CID 560600.
- ^ Executive Summary Bixin Archived July 21, 2011, at the Wayback 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. ISBN 9780128031384.