HYDROCARBONS 



347 



a'. Oxidation of Naphthalene to Naphthol: Bourne and Young^^* 

 demonstrated that naphthalene is partly oxidized in the a-position by- 

 dogs and by human subjects, to yield a-naphthol; this phenol is con- 

 jugated with glucuronic acid or sulfuric acid, and is then excreted in the 

 urine as the glucuronide or as ethereal sulfate. The fact that naphthalene, 

 when administered to human subjects and to dogs, gives rise to a com- 

 pound with glucuronic acid was reported by Lesnik and Nencki-^^ in 1886, 

 and later by Lesnik.^eo Bourne and Young^ei found this compound in the 

 case of rabbits; however, only minimal amounts were isolated. Lesnik^'o 

 was able to isolate small amounts of the a-glucuronide from the urine of a 

 man after 12 g. of naphthalene had been administered. However, Umezawa 

 and Masamune-^2 confirmed this finding in the case of the rabbit. The 

 reactions involved in the formation of the a-naphthol and its detoxication 

 are pictured below : 



O + H2O 



Naphthalene 



a-Naphthol 



COOH 



a-Naphthol glucuronide 



Potassium a-naphthol 

 sulfate 



The Detoxication of Naphthalene by Oxidation to a-Naphthol, and Its Conjugation 

 with Glucuronic Acid or with Potassium Hydrogen Sulfate^^* 



b'. Formation of L-a-Naphthylmercapturic Acid: When naphthalene 

 is given to rabbits, one product formed in a considerable amount is L-a- 

 naphthylmercapturic acid. This compound is analogous to the L-phenyl- 

 mercapturic acid formed in the metabolism of benzene. Bourne and 



"8 M. C. Bourne and L. Young, Chemistry & Industry, 52 {11), 271 (1933). 

 "9 M. Lesnik and M. Nencki, Ber., 19, 1534-1538 (1886). 



*** M. Lesnik, Naunyn-Schmiedeberg' s Arch, exptl. Pathol. Pharmakol., S4, 167-179 

 (1888). 



«i M. C. Bourne and L. Young, Biochem. J., 28, 803-808 (1934). 



*•* S. Umezawa and H. Masamune, /. Biochem. {Japan), 28. 487-493 (1938). 



