Partial Synthesis and Characterization of the Monoand Diepoxides of β-Cryptoxanthin

Péter Molnár, József Deli, Zoltán Matus, Gyula Tóth, Andrea Steck, Hanspeter Pfander

Research output: Article

7 Citations (Scopus)

Abstract

β-Cryptoxanthin (1) was acetylated and then epoxidized with monoperoxyphthalic acid. After hydrolysis, repeated chromatography, and crystallization, (3S,5R,6S)-5,6-epoxy-β-cryptoxanthin (3), (3S,5S,6R)-5,6-epoxy-β-cryptoxanthin (4), (3R,5′R,6′S)-5′,6′-epoxy-β-cryptoxanthin (5), (3S,5R,6S,5′R,6′S)-5,6:5′,6′-diepoxy-β- cryptoxanthin (6), and (3S,5S,6R,5′S,6′R)-5,6:5′,6′-diepoxy-β- cryptoxanthin (7) were isolated as main products and characterized by their UV/VIS, CD, 1H- and 13C-NMR, and mass spectra. The comparison of the carotenoid isolated from yellow, tomato-shaped paprika (Capsicum annuum var. lycopersiciforme flavum) with 3-5 strongly supports the structure of 3 for the natural product.

Original languageEnglish
Pages (from-to)221-229
Number of pages9
JournalHelvetica Chimica Acta
Volume80
Issue number1
DOIs
Publication statusPublished - jan. 1 1997

ASJC Scopus subject areas

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

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