Process for making metabolites of lycopene
US6008417A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Oct 7, 1998 |
| Grant date | Dec 28, 1999 |
| Priority date | — |
| Expiry date | Oct 7, 2018 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07C2601/08
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
The invention is concerned with a multi-stage process for making an oxidative metabolite of the carotenoid lycopene, 2,6-cyclolycopene-1,5-diol having the formula ##STR1## In this process .alpha.-terpinyl acetate is oxidatively dihydroxylated to a cyclohexanediol (IV), the cyclohexanediol (IV) is oxidatively cleaved to a ketoaldehyde (V), the ketoaldehyde (V) is subjected to an intramolecular aldol condensation to give a cyclopentanol (VI), the cyclopentanol (VI) is silylated to its silylated derivative formylcylopentane (VII), the formylcyclopentane (VII) is subjected to a C.sub.3 -chain lengthening with acetone and simultaneously to a saponification for the cleavage of the acetyl group to give a cyclopentylbutenone (VIII), the cyclopentylbutenone (VIII) is reacted with vinyl magnesium bromide to give a pentadienol (IX), the pentadienol (IX) is converted with deprotection of the silylated hydroxy group into a phosphonium salt (X), this salt is subjected to a Wittig reaction with 2,7-dimethyl-2,4,6-octatriene-1,8-dial to give a tridecahexaenal (XII) and the tridecahexaenal (XII) is subjected to a Wittig reaction with a (3,7,11-trimethyl-dodeca-2,4,6,10-tetraenyl)triphenylphosphoniu…
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.