Mercapturic acid metabolites from 2-, 3-, and 4-ethenyl-methylbenzenes in the rat.
N-Acetyl-L-cysteine was reacted with 2-(2-, 3-, or 4-methylphenyl)-oxiranes to give mixtures of the two possible regio isomers N-acetyl-S-[1-(2-, 3-, or 4-methylphenyl)-2-hydroxyethyl]-L-cysteine and N-acetyl-S-[2-(2-, 3-, or 4-methylphenyl)-2-hydroxyethyl]-L-cysteine, respectively. These were isolated in pure form by h.p.l.c.. The diastereomers were characterized by n.m.r. and mass spectrometry. The 2-, 3- and 4-ethenyl-methylbenzenes and the 2-(2-, 3-, and 4-methylphenyl)-oxiranes were injected i.p. into rats. G.l.c.-mass spectrometry showed similar patterns of acidic metabolites in the urine. Comparison with authentic mass spectra showed that the N-acetyl-S-[1-(methylphenyl)-2-hydroxyethyl]-L-cysteines accounted for over 80% of the mercapturic acids.
D000111:Acetylcysteine / Q000652:urine*; D000818:Animals; D001711:Biotransformation; D004852:Epoxy Compounds / Q000378:metabolism*; D004988:Ethers, Cyclic / Q000378:metabolism*; D007274:Injections, Intraperitoneal; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D013058:Mass Spectrometry; D051381:Rats; D011919:Rats, Inbred Strains; D013329:Structure-Activity Relationship; D013343:Styrenes / Q000378:metabolism*
D004852:Epoxy Compounds; D004988:Ethers, Cyclic; D013343:Styrenes; C033330:4-vinyltoluene oxide; C042269:2-(3-methylphenyl)oxirane; C042271:2-(2-methylphenyl)oxirane; C042273:1-ethenyl-2-methylbenzene; C042272:1-ethenyl-4-methylbenzene; C042274:1-ethenyl-3-methylbenzene; D000111:Acetylcysteine