Biosynthesis of mercapturic acids from allyl alcohol, allyl esters and acrolein

Abstract

3 Hydroxypropylmercapturic acid, i.e. N acetyl S (3 hydroxypropyl) L cysteine, was isolated, as its dicyclohexylammonium salt, from the urine of rats after the subcutaneous injection of each of the following compounds: allyl alcohol, allyl formate, allyl propionate, allyl nitrate, acrolein and S (3 hydroxypropyl) L cysteine. Allylmercapturic acid, i.e. N acetyl S allyl L cysteine, was isolated from the urine of rats after the subcutaneous injection of each of the following compounds: triallyl phosphate, sodium allyl sulphate and allyl nitrate. The sulphoxide of allylmercapturic acid was detected in the urine excreted by these rats. 3 Hydroxypropylmercapturic acid was identified by g.l.c. as a metabolite of allyl acetate, allyl stearate, allyl benzoate, diallyl phthalate, allyl nitrite, triallyl phosphate and sodium allyl sulphate. S (3 hydroxypropyl) L cysteine was detected in the bile of a rat dosed with allyl acetate.