HYDROCARBONS 333 



a". Conjugation with Sulfuric Acid. As early as 1876, Baumann-^^ 

 proved that administered phenol is conjugated with sulfuric acid to form 

 phenyl sulfate. 



Potassium phenyl 

 sulfate 



The Conjugation of Phenol with Potassium Acid Sulfate to Form Phenyl Sulfate 



Because of the relative difficulty in hydrolysis of the phenyl sulfate, it is 

 evident that the bond is firmer than that possessed by the inorganic salts. 

 Such compounds constitute the so-called "ethereal sulfate" fraction of the 

 urine. In addition to phenol itself, quinol, catechol, and hydroxyquinol 

 have been shown to be present in the ethereal sulfate fraction of the 

 urine. ^^^ 



A number of workers, including Christiani,''"- Rhode, -"^ Sperber,-"'* and 

 Garton and Williams, ^^^ showed that, when the potassium or sodium salts 

 of phenylsulfuric acid were fed or injected, they were excreted unchanged 

 in a practically quantitative amount. Garton and Williams'^* confirmed 

 the presence of small amounts of quinol (estimated as 0.3% of the dose) in 

 the urine of rabbits after the feeding of phenyl sulfate. Moreover, ex- 

 tremely small quantities of catechol and hydroxyquinol were also de- 

 tected. ^^^ The presence of the quinol and of other polyphenols could 

 have resulted from a slight hydrolysis of the phenyl sulfate through the 

 action of the phenyl sulfatase in the gut. Although the direct oxidation 

 of the phenyl sulfate to the quinol derivative cannot be completely ex- 

 cluded, it is beheved that the polyphenols result from the oxidation of free 

 phenol rather than from that of conjugated phenol. The unusually rapid 

 disposal of the injected sodium or potassium salts of phenyl sulfuric acid 

 is indicated by the fact that Sperber^"^ accounted for 75% of the amount 

 injected in the urine of hens w'ithin eighty minutes after the injection was 

 made.^^^ 



b". Conjugation w^ith Glucuronic Acid. Glucuronic acid affords an 

 important detoxicating mechanism, not only for phenol itself and for the 



201 E. Baumann, Arch. ges. Physiol. (Pfluger's), 13, 285-308 (1876). 



»>2 A. Christiani, Z. physiol. Chem., 2, 273-287 (1878). 



«»» H. Rhode, Z. physiol. Chem., 12^, 15-36 (1923). 



^* I. Sperber, Kgl. Lantbruks.-Hogskol. Ann. (Ann. Roy. Agr. Coll., Sweden), 15, 317- 

 349 (1948); Chem. Abst., A2, 6440 (1948); cited by G. A. Garton and R. T. Williams , 

 Biochem. J., 4S, 158-163 (1949); pp. lo8, 159. 



