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

✍ Scribed by Péter Molnár; József Deli; Zoltán Matus; Gyula Tóth; Andrea Steck; Hanspeter Pfander

Publisher
John Wiley and Sons
Year
1997
Tongue
German
Weight
469 KB
Volume
80
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

β‐Cryptoxanthin (1) was acetylated and then epoxidized with monoperoxyphthalic acid. After hydrolysis, repeated chromatography, and crystallization, (3__S__,5__R__,6__S__)‐5,6‐epoxy‐β‐cryptoxanthin (3), (3__S__,5__S__,6__R__)‐5,6‐epoxy‐β‐cryptoxanthin (4), (3__R__,5′R,6′R)‐5′,6′‐epoxy‐β‐cryptoxanthin (5), (3__S__,5__R__,6__S__,5′R,6′S)‐5,6:5′,6′‐diepoxy‐β‐cryp‐toxanthin (6), and (3__S__,5__S__,6__R__,5′S,6′R)‐5,6:5′,6′‐diepoxy‐β‐cryptoxanthin (7) were isolated as main products and characterized by their UV/VIS, CD, ^1^H‐ and ^13^C‐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.

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