Preparation and (E/Z)-Isomerization of the Diastereoisomers of Violaxanthin

Péter Molnár, József Deli, Ferenc Zsila, Andrea Steck, Hanspeter Pfander, Gyula Tóth

Research output: Article

9 Citations (Scopus)

Abstract

Violaxanthin A (=(all-E,3S,5S,6R,3′S,5′S,6′ R)-5,6:5′,6′-diepoxy-5,6,5′,6′-tetrahydro-β, β-carotene-3,3′-diol = syn,syn-violaxanthin; 5) and violaxanthin B (=(all-E,3S,5S,6R,3′S,5′R,6′S)-5,6:5′, 6′-diepoxy-5,6,5′,6′-tetrahydro-β,β-carotene-3, 3′-diol = syn,anti-violaxanthin; 6) were prepared by epoxidation of zeaxanthin diacetate (1) with monoperphthalic acid. Violaxanthins 5 and 6 were submitted to thermal isomerization and I2-catalyzed photoisomerization. The structure of the main products, i.e., (9Z)-5, (13Z)-5, (9Z)-6, (9′Z)-6, (13Z)-6, and (13′Z)-6, was determined by their UV/VIS, CD, 1H-NMR, 13C-NMR, and mass spectra.

Original languageEnglish
Pages (from-to)11-27
Number of pages17
JournalHelvetica Chimica Acta
Volume87
Issue number1
DOIs
Publication statusPublished - márc. 5 2004

ASJC Scopus subject areas

  • Catalysis
  • Biochemistry
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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