Biochemical studies of toxic agents. 6. The conversion of naphthalene into 1:2-dihydro-2-hydroxy-1-naphthyl glucosiduronic acid in the rabbit

Abstract

The glucuronide content of the urine of rabbits is greatly increased after admn. of naphthalene by stomach tube. A glucuronide fraction separated from the urine after admn. of naphthalene gave 1-naphthyl glucosiduronic acid on treatment with hot, dilute acid. Incubation of the glucuronide fraction with beta-glucuroni-dase liberated dextrorotatory l:2-dihydronaphthalene_1:2-diol. These findings are consistent with the presence of 1:2_dihydro-2_hydroxy-l-naphthyl glucosiduronic,acid in the glucuronide fraction, and this was confirmed by the prepn. of a tetraacetate methyl ester, methyl (l:2_dihydro-2-acetoxy-l_naphthyl trio.O.acetyl-glucosid) uronate, from this fraction. From the urine of rabbits dosed with 1- and 2-naphthol by stomach tube, it was possible to isolate 1- and 2-naphthyl glucosiduronic acid, respectively. Methyl (1- and 2-naphthyl tri-O-acetylglucosid) uronates were prepared.