View source for Bixin

{{Chembox
| Verifiedfields = changed
| verifiedrevid = 459980646
| Reference = <ref name="Merck">''[[Merck Index]]'', 11th Edition, '''1320'''</ref>
| ImageFile = Bixina.svg
| ImageSize = 300
| ImageName = Skeletal formula
| IUPACName = (2''E'',4''E'',6''E'',8''E'',10''E'',12''E'',14''E'',16''Z'',18''E'')-20-Methoxy-4,8,13,17-tetramethyl-20-oxoicosa-2,4,6,8,10,12,14,16,18-nonaenoic acid
| OtherNames = ''cis''-Bixin; α-Bixin; 9-''cis''-6,6'-Diapo-ψ,ψ-carotenedioic acid, 6-methyl ester
| Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4444638
| ChEBI = 3136
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1172615
| InChI = 1/C25H30O4/c1-20(12-8-14-22(3)16-18-24(26)27)10-6-7-11-21(2)13-9-15-23(4)17-19-25(28)29-5/h6-19H,1-5H3,(H,26,27)/b7-6+,12-8+,13-9+,18-16+,19-17+,20-10+,21-11+,22-14+,23-15-
| InChIKey = RAFGELQLHMBRHD-SLEZCNMEBU
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 6983-79-5
| CASNo2_Ref = {{cascite|correct|CAS}}
| CASNo2 = 39937-23-0
| CASNo2_Comment = (''trans'')
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C25H30O4/c1-20(12-8-14-22(3)16-18-24(26)27)10-6-7-11-21(2)13-9-15-23(4)17-19-25(28)29-5/h6-19H,1-5H3,(H,26,27)/b7-6+,12-8+,13-9+,18-16+,19-17+,20-10+,21-11+,22-14+,23-15+
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = RAFGELQLHMBRHD-IFNPSABLSA-N
| PubChem = 5281226
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 9L7T4VB66G
| UNII1_Ref = {{fdacite|correct|FDA}}
| UNII1 = 6JH6LEZ7HY
| UNII1_Comment = (''trans'')
| SMILES = O=C(O)\C=C\C(=C\C=C\C(=C\C=C\C=C(\C=C\C=C(/C=C/C(=O)OC)C)C)C)C
}}
| Section2 = {{Chembox Properties
| C=25 | H=30 | O=4
| Appearance = Orange crystals
| Density =
| MeltingPt = 198 °C (cis-isomer) <br /> 217 °C (trans-isomer)
| BoilingPt =
| Solubility = Insoluble}}
| Section3 = {{Chembox Hazards
|  NFPA-H = 1
|  NFPA-F = 1
|  NFPA-R = 0
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
'''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>
==Applications==
:[[image:Bixa orellana fruit open.jpg|thumb|center|Red seeds of the achiote tree]]
:[[file:CheetosCrop.jpg|thumb|Bixin is one of the colorants used in the snack Cheetos.]]
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>
==Chemical properties==
Bixin is unstable. It [[isomerization|isomerizes]] into ''trans''-bixin (β-bixin), the [[Cis-trans isomerism|double-bond isomer]].<ref name="Merck"/>
:[[File:Trans-bixin.png|thumb|center|320px|Chemical structure of ''trans''-bixin]]
Bixin is soluble in fats and [[alcohols]] but insoluble in water. Upon exposure to [[alkali]], the [[methyl]] [[ester]] is [[hydrolysis|hydrolyzed]] to produce the [[dicarboxylic acid]] '''norbixin''', a water-soluble derivative.
:[[File:norbixin structure.png|thumb|center|300px|Chemical structure of norbixin]]{{clear-left}}
==References==
{{reflist}}
{{carotenoids}}
[[Category:Apocarotenoids]]
[[Category:E-number additives]]