HYDROCARBONS 



331 



rabbits after the injection of benzene. The presence of an additional 

 polyhydroxyquinol has been indicated in more recent work.^^^-^*^ Since 

 it is a qiiinol derivative, the only possible formula is 



OH 

 /\0H 



Garton and Wilhams/^^ on the basis of earlier work of Porteous and 

 Williams/*'-^*" and of their own/^^-^^^ postulated the following scheme to 

 illustrate the sequence of the formation of the several phenols in the 

 oxidation of benzene: 



Benzene 



ca. 20% 



phenol 



-> catechol 



conjugated 

 phenol 



conjugated 

 quinol 



conjugated 

 catechol 



-^ hydroxyquinol ' 



conjugated 

 hydroxyquinol 



Toxic 

 compounds 



Detoxicated 

 compounds 



According to the scheme of Garton and Williams, ^^^ it is the free phenol 

 rather than conjugated phenol which gives rise to the polyphenols. These 

 workers offered extensive evidence of the validity of these reactions. 



Porteous and Williams^*" observed that, when benzene is oxidized, quinol 

 and catechol are produced in equal amounts, while ten times as much 

 quinol is generated as catechol when phenol itself is oxidized. This led 

 Garton and Williams'*^ to adopt the theory that a part of the benzene is 

 first oxidized to an unknown intermediate, which is converted to catechol 

 without the intermediation of phenol. It is suggested that the miknown 

 intermediate may possibly be l,2-dihydro-l,2-dihydroxybenzene or di- 

 hydroxycycZohexadiene. The suggestion that this compound may serve 

 in the above capacity is based upon the fact that compounds with similar 

 structures have been isolated as metabohtes of naphthalene,"^'^^'' anthra- 

 cene, ^^^-^^^ and phenanthrene.^^^ When benzene was administered orally 



88 G. A. Garton and R. T. Williams, Biochem. J., 46, 158-163 (1949). 



89 J. W. Porteous and R. T. Williams, Biochem. J., U, 46-55 (1949). 

 9" J. W. Porteous and R. T. WUliams, Biochem. J., 44, 56-61 (1949). 

 " G. A. Garton and R. T. WilUams, Biochem. J., 43, 206-211 (1948). 

 92 G. A. Garton and R. T. Williams, Biochem. J., 44, 234-238 (1949). 



95 L. Young, Biochem. J., 41, 417^22 (1947). 

 9< J. Booth and E. Bovland, Biochem. J., 41, xxix (1947). 

 9^^ E. Boyland and A. A. Levi, Biochem. J., 29, 2679-2683 (1935). 



96 E. Boyland and A. A. Levi, Biochem. J., SO, 728-731, 1225-1227 (1936). 

 •^ E. Boyland and G. Wolf, Biochem. J., 42, xxxii (1948). 



