Biosynthesis of mercapturic acids from allyl alcohol, allyl esters and acrolein.
1. 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. 2. 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. 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. 4. S-(3-Hydroxypropyl)-l-cysteine was detected in the bile of a rat dosed with allyl acetate.
D000111:Acetylcysteine / Q000096:biosynthesis*; D000171:Acrolein / Q000378:metabolism; D000438:Alcohols / Q000378:metabolism; D000447:Aldehydes / Q000378:metabolism*; D000498:Allyl Compounds / Q000378:metabolism*; D000818:Animals; D001646:Bile / Q000032:analysis; D002854:Chromatography, Paper; D004952:Esters / Q000378:metabolism; D005561:Formates / Q000378:metabolism; D007279:Injections, Subcutaneous; D008297:Male; D009566:Nitrates / Q000378:metabolism; D010710:Phosphates / Q000378:metabolism; D011422:Propionates / Q000378:metabolism; D051381:Rats; D013454:Sulfoxides / Q000652:urine; D013460:Sulfur Isotopes
D000438:Alcohols; D000447:Aldehydes; D000498:Allyl Compounds; D004952:Esters; D005561:Formates; D009566:Nitrates; D010710:Phosphates; D011422:Propionates; D013454:Sulfoxides; D013460:Sulfur Isotopes; D000171:Acrolein; D000111:Acetylcysteine