Studies in detoxication. 46. The metabolism of aliphatic alcohols. The glucuronic acid conjugation of acyclic aliphatic alcohols

Abstract

In the rabbit 30 aliphatic alcohols were found to conjugate to some extent. The conjugation of normal primary alcohols from methyl to decyl was found to be low, being less than 10% of the dose, but its occurrence was proved by isolation. The conjugation of secondary alcohols increased with increasing number of C atoms in the molecule from 10% with isopropanol to 60-70% for the secondary heptyl alcohols. With octan-2-ol the conjugation was low. The oxidation products of some of the secondary alcohols (isopropanol, butan-2-ol and heptan-2-ol) were proved to be ketones. The conjugation of 3 tertiary alcohols, butyl, amyl and hexyl, was higher than that of the corresponding primary and secondary alcohols. The results suggest that conjugation is an alternative metabolic process to oxidation. The order of conjugation is tertiary>secondary > primary, which is the reverse of the order for ease of oxidation. In most cases the glucuronides were isolated and characterized as triacetyl methyl esters. Aliphatic alcohols do not appear to form ethereal sulfates.