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Partial Synthesis and Characterization of Karpoxanthins and Cucurbitaxanthin A Epimers
Author(s) -
Molnár Péter,
Deli József,
Matus Zoltán,
Tóth Gyula,
Steck Andrea,
Pfander Hanspeter
Publication year - 1999
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/(sici)1522-2675(19991110)82:11<1994::aid-hlca1994>3.0.co;2-9
Subject(s) - chemistry , epimer , stereochemistry , hydrolysis , diol , antheraxanthin , organic chemistry , carotenoid , zeaxanthin , biochemistry , lutein
Karpoxanthin (=(all‐ E ,3 S ,5 R ,6 R ,3′ R )‐5,6‐dihydro‐ β , β ‐carotene‐3,5,6,3′‐tetrol; 7 ), 6‐epikarpoxanthin (=(all‐ E ,3 S ,5 R ,6 S ,3′ R )‐5,6‐dihydro‐ β , β ‐carotene‐3,5,6,3′‐tetrol; 4 ), 5‐epikarpoxanthin (=(all‐ E ,3 S ,5 S ,6 R ,3′‐ R )‐5,6‐dihydro‐ β , β ‐carotene‐3,5,6,3′‐tetrol; 11 ), cucurbitaxanthin A (=(all‐ E ,3 S ,5 R ,6 R ,3′ R )‐3,6‐epoxy‐5,6‐dihydro‐ β , β ‐carotene‐5,3′‐diol; 10 ), epicucurbitaxanthin A (=(all‐ E ‐3 S ,5 S ,6 R ,3′ R )‐3,6‐epoxy‐5,6‐dihydro‐ β , β ‐carotene‐5,3′‐diol; 14 ), and the corresponding mutatoxanthin epimers 8 , 9 , 12 , and 13 were prepared in crystalline state by the acid‐catalyzed hydrolysis of (3 S ,5 R ,6 S ,3′ R )‐ and (3 S ,5 S ,6 R ,3′ R )‐antheraxanthin ( 5 and 6 , resp.) and characterized by their UV/VIS, CD, 1 H‐ and 13 C‐NMR, and mass spectra.