Jump to content

Bixin: Difference between revisions

From Wikipedia, the free encyclopedia
Browse history interactively
← Previous editNext edit →
Content deleted Content added
VisualWikitext
CheMoBot (talk | contribs)
Bots
141,565 edits
Updating {{chembox}} (changes to verified fields - updated 'CASNo2_Ref') per Chem/Drugbox validation (report errors or bugs)
Rescuing 1 sources and tagging 0 as dead. #IABot (v1.2.6)
Line 48: Line 48:
}}
}}


'''Bixin''' is an [[apocarotenoid]] found in [[annatto]], a natural [[food coloring]] obtained from the seeds of the [[Bixa orellana|achiote tree]] (''Bixa orellana''). Annatto seeds contain about 5% pigments, which consist of 70-80% bixin.<ref>[http://ntp-server.niehs.nih.gov/?objectid=F59ACAC5-F1F6-975E-7C563568F5F7351B#selection Executive Summary Bixin], National Toxicology Program</ref>
'''Bixin''' is an [[apocarotenoid]] found in [[annatto]], a natural [[food coloring]] obtained from the seeds of the [[Bixa orellana|achiote tree]] (''Bixa orellana''). Annatto seeds contain about 5% pigments, which consist of 70-80% bixin.<ref>[http://ntp-server.niehs.nih.gov/?objectid=F59ACAC5-F1F6-975E-7C563568F5F7351B#selection Executive Summary Bixin] {{wayback|url=http://ntp-server.niehs.nih.gov/?objectid=F59ACAC5-F1F6-975E-7C563568F5F7351B#selection |date=20110721000000 }}, National Toxicology Program</ref>


Bixin is chemically unstable when isolated and converts via [[isomerization]] into ''trans''-bixin (β-bixin), the [[Cis-trans isomerism|double-bond isomer]].<ref name="Merck"/>
Bixin is chemically unstable when isolated and converts via [[isomerization]] into ''trans''-bixin (β-bixin), the [[Cis-trans isomerism|double-bond isomer]].<ref name="Merck"/>

Revision as of 10:26, 3 November 2016

Bixin[1]
Skeletal formula
Ball-and-stick model
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)
ChEMBL
ChemSpider
ECHA InfoCard 100.027.499 Edit this at Wikidata
UNII
  • InChI=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+ checkY
    Key: RAFGELQLHMBRHD-IFNPSABLSA-N checkY
  • 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-
    Key: RAFGELQLHMBRHD-SLEZCNMEBU
  • 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
Properties
C25H30O4
Molar mass 394.511 g·mol−1
Appearance Orange crystals
Insoluble
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Bixin is an apocarotenoid found in annatto, a natural food coloring obtained from the seeds of the achiote tree (Bixa orellana). Annatto seeds contain about 5% pigments, which consist of 70-80% bixin.[2]

Bixin is chemically unstable when isolated and converts via isomerization into trans-bixin (β-bixin), the double-bond isomer.[1]

Bixin is soluble in fats 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 trans-bixin
Ball-and-stick model of trans-bixin
Chemical structure of norbixin

References

  1. ^ a b Merck Index, 11th Edition, 1320
  2. ^ Executive Summary Bixin Archived 2011-07-21 at the Wayback Machine, National Toxicology Program
Retrieved from "https://en.wikipedia.org/enwiki/w/index.php?title=Bixin&oldid=747612827"