Effective synthesis of sulfate metabolites of chlorinated phenols

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

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

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.

Original languageEnglish
Pages (from-to)1965-1971
Number of pages7
JournalChemosphere
Volume93
Issue number9
DOIs
StatePublished - Nov 2013

Bibliographical note

Funding Information:
This research was supported by Grants ES05605 , ES013661 and ES017425 from the National Institute of Environmental Health Sciences , National Institutes of Health (NIEHS/NIH). Contents of this manuscript are solely the responsibility of the authors and do not necessarily represent the official views of the NIEHS/NIH.

Keywords

  • Chlorophenol
  • Metabolites
  • Pentachlorophenol
  • Sulfates
  • X-ray crystal structure

ASJC Scopus subject areas

  • General Chemistry
  • Public Health, Environmental and Occupational Health
  • Pollution
  • Health, Toxicology and Mutagenesis
  • Environmental Engineering
  • Environmental Chemistry

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