Acid-catalyzed isomerization of fucosterol and Δ5-avenasterol

Afaf Kamal-Eldin, Kaisu Määttä, Jari Toivo, Anna Maija Lampi, Vieno Piironen

Research output: Contribution to journalArticlepeer-review

64 Citations (Scopus)

Abstract

This work shows that fucosterol, Δ5-avenasterol, and similar ethylidene-side chain sterols can undergo acid-catalyzed isomerization to give a mixture of five isomers. Four isomers formed from fucosterol were analyzed, using gas chromatography-mass spectrometry, and were characterized as Δ5-avenasterol, two Δ5,23-stigmastadienols, and Δ(5,24(25))- stigmastadienol. When the unsaponifiables fraction from oat oil was subjected to acid hydrolysis, the two Δ5,23-stigmastadienol isomers and Δ(5,24(25))-stigmastadienol were detected while fucosterol coeluted with sitosterol. Interisomerization of ethylidene-side chain sterols represents a limitation to the use of the acid hydrolysis method in the determination of sterols in food and other plant materials rich in these sterols, e.g., oat lipids.

Original languageEnglish
Pages (from-to)1073-1077
Number of pages5
JournalLipids
Volume33
Issue number11
DOIs
Publication statusPublished - 1998
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Cell Biology

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