Synthesis of bixin and three minor carotenoids from annatto (Bixa orellana)

Authors
Haberli, A Pfander, H
Citation
A. Haberli et H. Pfander, Synthesis of bixin and three minor carotenoids from annatto (Bixa orellana), HELV CHIM A, 82(5), 1999, pp. 696-706
Citations number
16
Categorie Soggetti
Chemistry & Analysis",Chemistry
Journal title
HELVETICA CHIMICA ACTA
ISSN journal
0018019X → ACNP
Volume
82
Issue
5
Year of publication
1999
Pages
696 - 706
Database
ISI
SICI code
0018-019X(1999)82:5<696:SOBATM>2.0.ZU;2-G
Abstract
The three apocarotenoids methyl (9Z)-8'-oxo-6,8'-diapocaroten-6-oate (2), m ethyl (9Z)-10'-oxo-6,10'diapocaroten-6-oate (4). and methyl (9Z)-14'-oxo-6, 14'-diapocaroten-6-oate (5), recently isolated from annatto, were synthesiz ed. The key step of all three syntheses was the Wittig reaction of the (Z)- terminus 6 with the phosphonium salts 15, 18, and 24, carrying the polyene chain. Bixin (1) was synthesized from 2 in a Horner-Emmons reaction.