title: Effective synthesis of sulfate metabolites of chlorinated phenols.
abstract: Chlorophenols are an important class of persistent environmental contaminants and have been implicated in a range of adverse health effects, including cancer. They are readily conjugated and excreted as the corresponding glucuronides and sulfates in the urine of humans and other species. Here we report the synthesis and characterization of a series of ten chlorophenol sulfates by sulfation of the corresponding chlorophenols with 2,2,2-trichloroethyl (TCE) chlorosulfate using N,N-dimethylaminopyridine (DMAP) as base. Deprotection of the chlorophenol diesters with zinc powder/ammonium formate yielded the respective chlorophenol sulfate ammonium salts in good yield. The molecular structure of three TCE-protected chlorophenol sulfate diesters and one chlorophenol sulfate monoester were confirmed by X-ray crystal structure analysis. The chlorophenol sulfates were stable for several months if stored at -20 °C and, thus, are useful for future toxicological, environmental and human biomonitoring studies.
authors.affiliation: Department of Occupational and Environmental Health, College of Public Health, The University of Iowa, Iowa City, IA 52242, USA. Electronic address: hans-joachim-lehmler@uiowa.edu.
authors.forename: Hans-Joachim
authors.initials: HJ
authors.lastname: Lehmler
authors.forename: Xianran
authors.initials: X
authors.lastname: He
authors.forename: Xueshu
authors.initials: X
authors.lastname: Li
authors.forename: Michael W
authors.initials: MW
authors.lastname: Duffel
authors.forename: Sean
authors.initials: S
authors.lastname: Parkin
mesh_terms: D001673:Biodegradation, Environmental; D002733:Chlorophenols / Q000032:analysis / Q000378:metabolism*; D004784:Environmental Monitoring; D004785:Environmental Pollutants / Q000032:analysis / Q000378:metabolism*; D008956:Models, Chemical; D010636:Phenols / Q000032:analysis / Q000378:metabolism*; D013431:Sulfates / Q000032:analysis / Q000378:metabolism*
chemical_list: D002733:Chlorophenols; D004785:Environmental Pollutants; D010636:Phenols; D013431:Sulfates
keywords: Chlorophenol; Metabolites; Pentachlorophenol; Sulfates; X-ray crystal structure
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