Formation of a Predominant Metabolite of Hydroxydihydrocarvone Evaluated by a Biomimetic Oxidative Model and in Rat Liver Microsomes

Abstract

This paper reports the biomimetic oxidation of hydroxydihydrocarvone by iodosylbenzene using tetraphenyl-porphine iron(III) chloride as the catalyst in ethyl acetate. Mass spectrometry fragmentation maps of hydroxydihydrocarvone (obtained by gas chromatography-mass spectrometry analyses) allowed for the identification of the major product as 4-hydroxy-5-(2-hydroxypropan-2-yl)-2-methylcyclohex-2-en-1-one (4-hydroxy-hydroxydihydrocarvone). This compound was also observed in an in vitro metabolism assay that employed isolated rat liver microsomes, thereby validating the biomimetic procedure.