absorbed 



HYDROCARBONS 

 phenylglucuronide 



335 



Phenjdglucuronide 



50% 



destroyed in gut 



50% 



hydrolyzed in gut 



phenol 



polyphenols - 

 (small amounts) 



phenylsulfuric acid 



-> polyphenolsulfuric acid 



Fig. 5. The metabolic changes occuring when phenylglucuronide is given orally. ^^ 



rabbits and dogs which had received benzene. According to chemical 

 nomenclature, it is described as hexa-2:4-diene-l:6-dioic acid. Muconic 

 acid can occur in three different isomeric forms, which are identified as cis- 

 cis, cis-trans, and trans-trans. Various findings have been reported. -^°~^^^ 

 All the samples of muconic acid isolated from the urine by Thierfelder and 

 Klenk,2io by Drummond and Fonar,^^^ and by Parke and Williams, "^-^^^ 

 were trans-trans. Mori^^ and Neumaerker-^- failed to find the acid in the 

 urine of rabbits after the administration of high doses of benzene. Bern- 

 hard and Gressly-^^ found traces, following its injection into animals. 

 Fuchs and Soos-^^ found muconic acid, but gave no definite evidence as to 

 its isomeric form. Boeseken et aZ.^^^~^^^ considered it to be cis-cis. Klein- 

 zeller and Fencl-^^ reported that an unnamed microorganism isolated from 

 waste waters, which was related to Micrococcus sphaeroides (from manure 

 and soil) oxidized benzene solely to ^rans-/mns-muconic acid. 



It would be expected that cis-cis muconic acid would be the isomer 

 which should be present in the urine if the muconic acid originated from 



209 M. Jaffe, Z. physiol. Chem., 62, 58-67 (1909). 



^'o H. Thierfelder and E. Klenk, Z. physiol. Chem., 141, 29-32 (1924). 



2" K. Bernhard and E. Gressly, Helv. Chim. Acta, 24, 83-87 (1941). 



212 H. Neumaerker, Z. physiol. Chem., 126, 203-209 (1923). 



213 D. Fuchs and A. v. Soos, Z. physiol. Chem., 98, 11-13 (1916). 



2" D. V. Parke and R. T. Williams, Biochem. J., 51, 339-348 (1952). 



215 J. Boeseken and R. Engelberts, Proc. Acad. Sci., Amsterdam, 34, 1292 (1931); 85, 

 750-755(1932). 



216 J. Boeseken and C. L. M. Kerkhoven, Rsc. trav. chim., 51, 964-970 (1932). 



21' J. Boeseken and G. Sloof, Proc. Acad. Sci. Amsterdam, 32, 1043-1045 (1929). 

 218 A. Kleinzeller and Z. Fencl, Chem. Listy, 46, 300-302 (1952); Chem. Abst., 47, 4290 

 (1953). 



