Trichloromethyl peroxyl radical (Cl3COO•) mediated oxidation of cholesterol

Research output: Contribution to journalArticle

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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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Cholesterol
chromatography
liquid chromatography
Thin layer chromatography
High performance liquid chromatography
Thin Layer Chromatography
oxidation
Oxidation
High Pressure Liquid Chromatography
Carbon tetrachloride
ionization
ammonia
Carbon Tetrachloride
mass spectrometry
Acetonitrile
Ammonia
Ionization
Mass spectrometry
Mass Spectrometry
carbon

ASJC Scopus subject areas

  • Environmental Science(all)
  • Environmental Chemistry

Cite this

Trichloromethyl peroxyl radical (Cl3COO•) mediated oxidation of cholesterol. / Kaphalia, Bhupendra; Ansari, Ghulam.

In: Chemosphere, Vol. 20, No. 1-2, 1990, p. 5-11.

Research output: Contribution to journalArticle

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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 3{\ss}-hydroxy-5-cholesten-7-one, 5-cholesten-3{\ss}, 7{\ss}- and 3{\ss}, 7α-diols and possibly 3{\ss}-hydroxy-5, 6ξ-epoxy-5ξ-cholestan-7-one as Cl3COO• mediated oxidation products of cholesterol.",
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