Bixin

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

CAS Number

* 6983-79-5 Y
* 39937-23-0 (trans) Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:3136

ChEMBL |

* ChEMBL1172615 N

ChemSpider |

* 4444638 N

PubChem CID

* 5281226

UNII |

* 9L7T4VB66G Y
* 6JH6LEZ7HY (trans) Y

InChI

* 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

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

Properties

Chemical formula

| C25H30O4
Molar mass | 394.511 g·mol−1
Appearance  | Orange crystals
Melting point | 198 °C (cis-isomer)
217 °C (trans-isomer)

Solubility in water

| 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).

N verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

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

thumb|center|Red seeds of the achiote tree
thumb|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

1. ↑ 1.0 1.1 Merck Index, 11th Edition, 1320
2. ↑ Bouvier, Florence; Dogbo, Odette; Camara, Bilal (2003). "Biosynthesis of the Food and Cosmetic Plant Pigment Bixin (Annatto)". Science 300 (5628): 2089–2091. doi:10.1126/science.1085162. ISSN 0036-8075. PMID 12829782. Bibcode: 2003Sci...300.2089B. https://www.jstor.org/stable/3834418.
3. ↑ Executive Summary Bixin , National Toxicology Program
4. ↑ 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.

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Carotenoids

Carotenes (C40)|

* α-Carotene
* β-Carotene
* γ-Carotene
* δ-Carotene
* ε-Carotene
* ζ-Carotene
* Lycopene
* Neurosporene
* Phytoene
* Phytofluene
* Torulene
* Lycopersene

Xanthophylls (C40)|

* Antheraxanthin
* Astaxanthin
* Canthaxanthin
* Citranaxanthin
* Cryptoxanthin
* Diadinoxanthin
* Diatoxanthin
* Dinoxanthin
* Echinenone
* Flavoxanthin
* Fucoxanthin
* Lutein
* Neoxanthin
* Rhodoxanthin
* Rubixanthin
* Violaxanthin
* Zeaxanthin
* Zeinoxanthin

Apocarotenoids (C<40)|

* Abscisic acid
* Apocarotenal
* Bixin
* Crocetin
* Food orange 7
* Ionones
* Peridinin

Vitamin A retinoids (C20)|

* Retinal
* Retinoic acid
* Retinol

Retinoid drugs|

* Acitretin
* Alitretinoin
* Bexarotene
* Etretinate
* Fenretinide
* Isotretinoin
* Tazarotene
* Temarotene
* Tretinoin
* Zuretinol acetate

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