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Partial Synthesis and Characterization of the Mono‐and Diepoxides of β‐Cryptoxanthin
Author(s) -
Molnár Péter,
Deli József,
Matus Zoltán,
Tóth Gyula,
Steck Andrea,
Pfander Hanspeter
Publication year - 1997
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19970800120
Subject(s) - chemistry , epoxy , carotenoid , hydrolysis , acid hydrolysis , acetylation , pigment , crystallization , stereochemistry , organic chemistry , food science , biochemistry , gene
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.