Studies in detoxication. 27. The orientation of conjugation in the metabolites of 4-chlorocatechol and 4-chlororesorcinol, with some observations on the fate of (+)-adrenaline, protocatechuic acid and protocatechuic aldehyde in the rabbit

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Abstract
A study was made of the conjugation of 4-chlorocatechol and chlororesorcinol in the rabbit. About 87% of 4-chlorocatechol is excreted as a glucuronide. Some 15% of chlorocatechol forms a mono-ethereal sulfate. Similarly 4-chlororesorcinol forms 78% of 4-chloro-3-hydroxyphenyl-glucuronide. Some 24% is excreted as ethereal sulfate. The orientation of conjugation in these 2 compounds is discussed, and it appears that conjugation takes place at the hydroxyl group para to the chloro group. (+)-Adrenaline forms 20% of glucuronide but practically no ethereal sulfate. The results suggest that (+)-adrenaline is conjugated on one of its phenolic hydroxyl groups. With protocatechuic acid, some 30% is conjugated and the rest is excreted unchanged. Protocatechuic aldehyde forms 2 glucuronides, is more highly conjugated than the acid and is largely transferred to protocatechuic acid and its conjugates.