Trichloromethyl peroxyl radical (Cl3COO•) mediated oxidation of cholesterol

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Abstract

Oxidation of cholesterol was studied in situ in a Cl3COO• generating system via a heterogenous reaction of carbon tetrachloride (CCl4), KO2 and 18-crown-6 in aprotic solvent (acetonitrile) at 10°C. The reaction mixture without CCl4 served as a control. Reaction performed with CCl4 showed the formation of products more polar than cholesterol which were separated by preparative thin layer chromatography (TLC) and purified by normal phase high performance liquid chromatography (HPLC). The data obtained collectively from TLC, HPLC and ammonia chemical ionization mass spectrometry confirmed the formation of 3ß-hydroxy-5-cholesten-7-one, 5-cholesten-3ß, 7ß- and 3ß, 7α-diols and possibly 3ß-hydroxy-5, 6ξ-epoxy-5ξ-cholestan-7-one as Cl3COO• mediated oxidation products of cholesterol.

Original languageEnglish (US)
Pages (from-to)5-11
Number of pages7
JournalChemosphere
Volume20
Issue number1-2
DOIs
StatePublished - 1990

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ASJC Scopus subject areas

  • Environmental Engineering
  • Environmental Chemistry
  • Chemistry(all)
  • Pollution
  • Health, Toxicology and Mutagenesis

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