The formation of 2-hydroxypropylmercapturic acid from 1-halogenopropanes in the rat.
1. 2-Hydroxypropylmercapturic acid, i.e. N-acetyl-S-(2-hydroxypropyl)-l-cysteine, has been isolated, as the dicyclohexylammonium salt, from the urine of rats dosed with 1-bromopropane. 2. The formation of the same metabolite from 1-chloropropane, 1-iodopropane, 1,2-epoxypropane and 1-chloropropan-2-ol has been demonstrated by chromatographic examination of the urine excreted by rats after they had been dosed with these compounds. 3. (+)- and (-)-Dicyclohexylammonium 2-hydroxypropylmercapturate have been prepared by fractional crystallization of the mixture of isomers obtained by two methods: the reaction of 1,2-epoxypropane with l-cysteine followed by acetylation, and the reduction of 2-oxopropylmercapturic acid. 4. The following compounds have also been prepared: S-(3-hydroxypropyl)-l-cysteine, (+)- and (-)-S-(2-hydroxypropyl)-l-cysteine, dicyclohexylammonium 3-hydroxypropylmercapturate, (+)- and (-)-dicyclohexylammonium 2-hydroxy-1-methylethylmercapturate, and (+)- and (-)-dicyclohexylammonium 1-(ethoxycarbonyl)ethylmercapturate.
D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D002854:Chromatography, Paper; D003545:Cysteine / Q000652:urine*; D006846:Hydrocarbons, Halogenated / Q000378:metabolism*; D008297:Male; D009532:Nickel; D000644:Quaternary Ammonium Compounds / Q000032:analysis; D051381:Rats; D013057:Spectrum Analysis; D013438:Sulfhydryl Compounds / Q000096:biosynthesis*
D006846:Hydrocarbons, Halogenated; D000644:Quaternary Ammonium Compounds; D013438:Sulfhydryl Compounds; D009532:Nickel; D003545:Cysteine