bixin

{{Chembox

| Verifiedfields = changed

| verifiedrevid = 459980646

| Reference = Merck Index, 11th Edition, 1320

| ImageFile = Bixina.svg

| ImageSize = 300

| ImageName = Skeletal formula

| IUPACName = (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

| 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)
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 achiote tree (Bixa orellana){{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}} 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.[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