Metabolism of polycyclic compounds. 14. The conversion of naphthalene into compounds related to trans-1:2-dihydro-1:2-dihydroxynaphthalene by rabbits

Publisher Website
Google Scholar
Abstract
The isolation of the (+)- and (-) forms of trans-l,2-dihydro-2-hydroxy-l-naphthylglucosiduronic acid from the urine of rabbits dosed with naphthalene is described. The (-)-form forms a well-defined creatinine salt. Both the glucosiduronic acids were also isolated in the form of their tetra-acetyl methyl ester derivatives and a 3d derivative was shown to be that of trans-1,2-dihydro-l-hydroxy-2-naphthylglucosiduronic acid. Rabbits convert naphthalene into l-hydroxy-2-naphthyl sulphate, which is also formed when rabbits, rats and guinea pigs are treated with trans-l,2-dihydro-1,2-dihydroxynaphthalene. The ester was synthesized by the persulphate oxidation of 1-naphthol. Possible mechanisms of formation of the above-mentioned compounds in the animal body are discussed.