5- Phenylmercapturic acid

Popp W, Rauscher D, Muller G et al. 1994. Concentrations of benzene in blood and S-phenylmercapturic acid and l, /-muconic acid in urine in car mechanics. Int Arch Occup Environ Health 66 1-6. 

Stommel P, Muller G, Stucker W et al. 1989. Determination of S-phenylmercapturic acid in the urine-An improvement in the biological monitoring of benzene exposure. Carcinogenesis 10 279-282. 

The reaction of intracellular glutathione with benzene oxide-oxepin, the initial metabolite of benzene, is presumed to give l-(6 -glutathionyl)-cyclohexa-3,5-dien-2-ol, which undergoes dehydration to J-phenylglutathione, the precursor of J-phenylmercapturic acid. To validate the proposed route to J-phenylglutathione, reactions of benzene... 

It is assumed that phenols can conjugate directly with D-glucuronic acid or sulfuric acid. The scheme explains why phenols do not conjugate with mercapturic acid. Parke and Williams128 have recently shown that administration of phenylmercapturic acid or phenylcysteine to the rabbit is followed by the excretion of phenylcysteine, ester sulfates, and thio-phenol, and phenylcysteine also yields diphenyl disulfide. The thiol donor... 

Phase 1 oxidation products of benzene, including phenol, hydroquinone, catechol, 1,2,4-trihy-droxybenzene, and trans,Irans-muconic acid in urine, are evidence of exposure to benzene. Another substance observed in urine of individuals exposed to benzene is S-phenylmercapturic acid,... 

Boogaard PJ, van Sittert NJ. 1995. Biological monitoring of exposure to benzene a comparison between S-phenylmercapturic acid, trans,trans-muconic acid, and phenol. Occup Environ Med 52 611-620. 

Schafer F, Schad H, Weber L. 1993. Determination of phenylmercapturic acid in urine of benzene-exposed BDF-1 mice. J Chromatog 620 239-242. 

It is known that the metabolism of chlorobenzene in vivo leads to a variety of products including 4-chlorophenol, 4-chlorocatechol, 4-chloro-phenylmercapturic acid, and 4-chloro-l,2-fmn.s-dihydrodihydroxybenzene (26). When the metabolism of 4-deuterochlorobenzene was studied in this laboratory, 3-chlorophenol and an O-methylated chlorocatechol were isolated in addition to the products reported above (19). The products isolated, the proposed intermediates, and their deuterium contents are summarized in Figure 7. An intermediate, X, is postulated for this scheme... 

Benzene is metabolized to phenol in the human organism. The phenol is determined from the urine. Recent research has shown that the determination of S-phenylmercapturic acid and trans,trans-mucomc acid in the urine is more informative than the determination of phenol. 

Phenol and S-phenylmercapturic acid additional benzene metabolites... 

Maestri, L. Negri, S. Ferrari, M. Ghittori, S. Imbriani, M. Determination of urinary S-phenylmercapturic acid, as a specific metabolite of benzene, by liquid chromatography/ single quadrupole mass spectrometry. Rapid Commun. Mass Spectrom. 2005,19, 1139-1144. 

Schettgen, T. Musiol, A. Alt, A. Kraus, T. Fast determination of urinary S-phenylmercapturic acid (S-PMA) and S-henzyhnercapturic acid (S-BMA) by column-switching bquid chromatography-tandem mass spectrometry. J. Chromatogr. B, 2008,863, 283-292. 

When mercapturic acids were administered to rats, the recovery of the original material was quite variable. Marsden and Young (1958) found only 33% of a-naphthylmercapturic acid was excreted unchanged by rats. This was less than half of the neutral sulfur of the urine and it seems probable some naphthyl-L-cysteine was excreted. Parke and Williams (1951) found 45% of a dose of phenylmercapturic acid was excreted unchanged and 14% as phenylcysteine,... 

---