PT  - JOURNAL ARTICLE
AU  - W G Taylor
TI  - Hydroxylation of 3-acetyl-2-(2,6-dimethyl-5-heptenyl)oxazolidine by rat liver microsomes. Identification of some isomeric metabolites.
DP  - 1983 Sep 01
TA  - Drug Metabolism and Disposition
PG  - 404--410
VI  - 11
IP  - 5
4099  - http://dmd.aspetjournals.org/content/11/5/404.short
4100  - http://dmd.aspetjournals.org/content/11/5/404.full
SO  - Drug Metab Dispos1983 Sep 01; 11
AB  - The metabolism of nonradiolabeled, stereoisomeric mixtures of 3-acetyl-2-(2,6-dimethyl-5-heptenyl)oxazolidine (I), a new citronelial-based insect repellent, by induced and uninduced rat liver microsomes has been 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 I with selenium dioxide, the allylic methyl carbons of the isobutenyl group were identified as the major sites of oxidative metabolism, with two samples of I prepared from different sources of (+/-)-citronelial. Both 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 I, E alcohol (II), Z alcohol (III), and E aldehyde (IV) were detected in postsincubate extracts. From integration of peak areas, the mean ratio of II to III was 70:30 in 47 extracts.