Studies in detoxication. 33. The metabolism of halogenobenzenes. A comparison of the glucuronic acid, ethereal sulphate and mercapturic acid conjugations of chloro-, bromo- and iodo-benzenes and of the o-, m- and p-chlorophenols. Biosynthesis of o-, m- and p-chlorophenylglucuronides

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Abstract
A quantitative study was made in the rabbit of the elimination of chloro-, bromo- and iodo-benzene as ethereal sulfates, glucuronides and mercapturic acids. Three times as much oxidation occurs as conjugation with acetylcysteine and the ratio ethereal sulfate: glucuronide: mercapturic acid is approx. 3:3:2. The o-, m- and p-chlorophenols are excreted entirely as glucuronides and ethereal sulfates, there being no mercapturic acid formation. p-Chlorophenol is converted almost quantitatively into the corresponding glucuronide and ethereal sulfate, only about 0.1% being oxidized to 4-chlorocatechol which appears in the ethereal sulfate fraction. The glucuronides of the o-, m- and p-chlorophenols were isolated from urine and characterized as the corresponding glucuronidamides and triacetylglucuronidamides.