The enantioselective metabolism of 4-isopropenyltoluene in rabbits.
4-Isopropenyltoluene (8) was administered orally to rabbits and the following four optically active metabolites, 2-(p-tolyl)propanoic acid (10), p-(1-carboxyethyl)benzoic acid (11), 2-hydroxy-2-(p-tolyl)propanoic acid (12), and 2-(p-tolyl)-1,2-propanediol (13) were isolated from urine in addition to an optically inactive metabolite, 4-isopropenylbenzoic acid (9). The enantiomeric ratios of the metabolites 10 and 11 were respectively R/S = 33:67 and 39:61 (S predominance), whereas those of the metabolites 12 and 13 possessing a tertiary hydroxyl group were R/S = 77:23 and 84:16 respectively (R predominance). The presumed metabolic pathways of 8 in rabbits leading to these metabolites are discussed.
Matsumoto
T
T
Faculty of Integrated Arts and Sciences, University of Tokushima, Japan.
Ishida
T
T
Takeda
Y
Y
Yagi
J
J
D000818:Animals; D001565:Benzoates / Q000652:urine; D005260:Female; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D013058:Mass Spectrometry; D010648:Phenylacetates / Q000652:urine; D011422:Propionates / Q000652:urine; D011409:Propylene Glycols / Q000652:urine; D011817:Rabbits; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013343:Styrenes / Q000008:administration & dosage / Q000378:metabolism*; D014050:Toluene / Q000031:analogs & derivatives / Q000652:urine
D001565:Benzoates; D010648:Phenylacetates; D011422:Propionates; D011409:Propylene Glycols; D013343:Styrenes; C092899:4-(1-carboxyethyl)benozic acid; C092903:4-isopropenyltoluene; D014050:Toluene; C092902:2-hydroxy-2-(4-tolyl)propanoic acid; C055607:cumic acid; C092900:2-(4-tolyl)-1,2-propanediol; C092901:2-(4-tolyl)propanoic acid