Optimized thiol derivatizing reagent for the mass spectral analysis of disubstituted epoxy fatty acids

John W. Newman, Bruce D. Hammock

Research output: Contribution to journalArticle

20 Scopus citations

Abstract

A novel procedure is described for the derivatization of fatty acid epoxides in the presence of their corresponding diols. The acidic character of 2,3,5,6-tetrafluorobenzenethiol promotes favorable mass fragmentation of linoleate and arachidonate derived epoxide derivatives and reduces alkene isomerization to a manageable side reaction, eliminated through the addition of a thiol scavenger. After silylation, regioisomeric mixtures of epoxy- and dihydroxylipids are simultaneously detected and discriminated using gas chromatography with electron impact mass spectral detection. Silylated hydroxysulfanyloctadecanoids yielded instrumental detection limits of 5 pg/μl, sufficient sensitivity for the quantification of endogenous epoxylipids.

Original languageEnglish (US)
Pages (from-to)223-240
Number of pages18
JournalJournal of Chromatography A
Volume925
Issue number1-2
DOIs
StatePublished - Aug 3 2001

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Keywords

  • Derivatization, GC
  • Diols
  • Epoxides
  • Fatty acids
  • Lipids
  • Tetrafluorobenzenethiol

ASJC Scopus subject areas

  • Analytical Chemistry

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