Effect of cis/trans isomerism of beta-carotene on the ratios of volatile compounds produced during oxidative degradation.
beta-Carotene is, when cleaved, an important source of flavor and aroma compounds in fruits and flowers. Among these aroma compounds, the main degradation products are beta-ionone, 5,6-epoxy-beta-ionone, and dihydroactinidiolide (DHA), which are associated by flavorists and perfumers with fruity, floral, and woody notes. These three species can be produced by degradation of beta-carotene through an attack by enzyme-generated free radicals and a cleavage at the C9-C10 bond. This study investigated the influence of cis/trans isomerism at the C9-C10 bond on the production of beta-carotene degradation compounds, first with a predictive approach and then experimentally with different isomer mixtures. beta-Carotene solutions containing high ratios of 9-cis-isomers produced more DHA, suggesting a different pathway than for the transformation of all-trans-beta-carotene to ionone and DHA. These results are important in the search for financially viable processes to produce natural carotene-derived aroma compounds.
Waché
Yves
Y
Laboratoire de Microbiologie UMR UB/INRA 1082, ENSBANA, 1 esplanade Erasme, 21000 Dijon, France. ywache@u-bourgogne.fr
Bosser-DeRatuld
Aurélie
A
Lhuguenot
Jean-Claude
JC
Belin
Jean-Marc
JM
D035264:Flowers / Q000737:chemistry; D005638:Fruit / Q000737:chemistry; D007536:Isomerism; D045792:Norisoprenoids; D009812:Odorants / Q000032:analysis*; D010084:Oxidation-Reduction; D013729:Terpenes / Q000737:chemistry; D013816:Thermodynamics; D014835:Volatilization; D019207:beta Carotene / Q000737:chemistry*
D045792:Norisoprenoids; D013729:Terpenes; D019207:beta Carotene; C008157:beta-ionone