HYDROXYLATION OF 3-ACETYL-2-(2,6-DIMETHYL-5-HEPTENYL)OXAZOLIDINE BY RAT-LIVER MICROSOMES - IDENTIFICATION OF SOME ISOMERIC METABOLITES

  • 1 January 1983
    • journal article
    • research article
    • Vol. 11  (5) , 404-410
Abstract
The metabolism of nonradiolabeled, stereoisomeric mixtures of 3-acetyl-2-(2,6-dimethyl-5-heptenyl)oxazolidine (1), a new citronellal-based insect repellent, by induced and uninduced rat liver microsomes was examined in a NADPH-generating system at a substrate concentration of 1.67 mM. By comparison of retention times and mass spectra of the metabolites with the products from oxidation of 1 with SeO2, the allylic methyl C of the isobutenyl group were identified as the major sites of oxidative metabolism, with 2 samples of 1 prepared from different sources of(.+-.)-citronellal. Diastereomeric and E-Z isomeric forms of the metabolites were separated by high resolution capillary gas chromatography with Carbowax 20M-terephthalic acid. Diastereomeric mixtures of unmetabolized 1, E alcohol (2), Z alcohol (3) and E aldehyde (4) were detected in postincubate extracts. From integration of peak areas, the mean ratio of 2 to 3 was 70:30 in 47 extracts.

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