Affordable Access

Publisher Website

Oxidative degradation of β-carotene and β-apo-8′-carotenal

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
49
Issue
4
Identifiers
DOI: 10.1016/s0040-4020(01)80333-1
Disciplines
  • Chemistry

Abstract

Abstract In the self-initiated oxidation of β-carotene with molecular oxygen the rate of oxygen uptake was shown to depend on the oxygen partial pressure. Epoxides, dihydrofurans, carbonyl compounds, carbon dioxide, oligomeric material, traces of alcohols, and probably carboxylic acids were formed. The main products in the early stage of the oxidation were shown to be 5,6-epoxy-β-carotene. 15,15′-epoxy-β-carotene, diepoxides, and a series of β-apo-carotenals and -carotenones. As the oxidation proceeded uncharacterised oligomeric material and the carbonyl compounds became more important and the epoxides degraded. In the final phase of the oxidation the longer chain β-apo-carotenals were themselves oxidized to shorter chain carbonyl compounds, particularly β-apo-13-carotenone, β-ionone, 5,6-epoxy-gb-ionone, dihydroactinidiolide and probably carboxylic acids. The effect of iron, copper and zinc stearates on the product composition and proportions was studied, as was the effect of light. The oxidation was inhibited by 2,6-di- t-butyl-4-methylphenol and α-tocopherol. The oxidations of β-apo-8′-carotenal and retinal under similar conditions were studied briefly, and the main products from the former compound were characterized. The initiation, the formation of the epoxides, the β-apo-carotenals and -carotenones, the successive chain shortening of the aldehydes to the ketones, and the formation of dihydroactinidiolide are explained in terms of free radical peroxidation chemistry.

There are no comments yet on this publication. Be the first to share your thoughts.

Statistics

Seen <100 times
0 Comments

More articles like this

beta-Apo-8'-carotenal, but not beta-carotene, is a...

on Xenobiotica; the fate of forei... September 1996

Enzymatic oxidation of beta-apo-8'-carotenol to be...

on Biochemistry. Biokhimii︠a︡ July 1997
More articles like this..