Partial synthesis and characterization of the mono- and diepoxides of β-cryptoxanthin

P. Molnar, J. Deli, Z. Matus, G. Tóth, A. Steck, H. Pfander

Research output: Contribution to journalArticle

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 - 1997

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Chromatography
Hydrolysis
Crystallization
Nuclear magnetic resonance
tomatoes
carotenoids
Acids
chromatography
synthesis
products
mass spectra
hydrolysis
Capsicum
crystallization
nuclear magnetic resonance
acids
Carotenoids
Lycopersicon esculentum
Biological Products
Cryptoxanthins

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Partial synthesis and characterization of the mono- and diepoxides of β-cryptoxanthin. / Molnar, P.; Deli, J.; Matus, Z.; Tóth, G.; Steck, A.; Pfander, H.

In: Helvetica Chimica Acta, Vol. 80, No. 1, 1997, p. 221-229.

Research output: Contribution to journalArticle

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AU - Deli, J.

AU - Matus, Z.

AU - Tóth, G.

AU - Steck, A.

AU - Pfander, H.

PY - 1997

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