From Wikipedia, the free encyclopedia
Bixin
[1]
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
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.027.499
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+
Y Key: RAFGELQLHMBRHD-IFNPSABLSA-N
Y 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
C 25 H 30 O 4
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).
Chemical compound
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
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
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
^
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 .