Effective synthesis of sulfate metabolites of chlorinated phenols

Hans-Joachim Lehmler; Xianran He; Xueshu Li; Michael W Duffel; Sean Parkin

doi:10.1016/j.chemosphere.2013.06.087

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Effective synthesis of sulfate metabolites of chlorinated phenols

Journal article

Open access

Peer reviewed

Effective synthesis of sulfate metabolites of chlorinated phenols

Hans-Joachim Lehmler, Xianran He, Xueshu Li, Michael W Duffel and Sean Parkin

Chemosphere (Oxford), Vol.93(9), pp.1965-1971

11/2013

DOI: 10.1016/j.chemosphere.2013.06.087

PMCID: PMC3815985

PMID: 23906814

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Abstract

•Chlorophenol sulfates were prepared via trichloroethyl-protected sulfate diesters.•Ammonium salts of chlorophenol sulfates are stable for several months at −20°C.•Crystal structure analysis confirmed molecular structure of selected sulfate esters. 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.

Pentachlorophenol

X-ray crystal structure

Chlorophenol

Metabolites

Sulfates

Details

Title: Subtitle: Effective synthesis of sulfate metabolites of chlorinated phenols
Creators: Hans-Joachim Lehmler - Department of Occupational and Environmental Health, College of Public Health, The University of Iowa, Iowa City, IA 52242, USA
Xianran He - Department of Occupational and Environmental Health, College of Public Health, The University of Iowa, Iowa City, IA 52242, USA
Xueshu Li - Department of Occupational and Environmental Health, College of Public Health, The University of Iowa, Iowa City, IA 52242, USA
Michael W Duffel - Department of Pharmaceutical Sciences and Experimental Therapeutics, College of Pharmacy, The University of Iowa, Iowa City, IA 52242, USA
Sean Parkin - Department of Chemistry, University of Kentucky, Lexington, KY 40506, USA
Resource Type: Journal article
Publication Details: Chemosphere (Oxford), Vol.93(9), pp.1965-1971
DOI: 10.1016/j.chemosphere.2013.06.087
PMID: 23906814
PMCID: PMC3815985
NLM abbreviation: Chemosphere
ISSN: 0045-6535
eISSN: 1879-1298
Publisher: Elsevier Ltd
Grant note: DOI: 10.13039/100000002, name: National Institutes of Health; DOI: 10.13039/100000002, name: National Institutes of Health; DOI: 10.13039/100000066, name: National Institute of Environmental Health Sciences; DOI: 10.13039/100000066, name: National Institute of Environmental Health Sciences
Language: English
Date published: 11/2013
Academic Unit: Occupational and Environmental Health; Iowa Neuroscience Institute; Pharmaceutical Sciences and Experimental Therapeutics; Iowa Superfund Research Program; Medicinal and Natural Products Chemistry
Record Identifier: 9984001080302771

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