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(all‐ E )‐12′‐Apozeaxanthinol, Persicaxanthine und Persicachrome
Author(s) -
MärkiFischer Edith,
Eugster Conrad Hans
Publication year - 1988
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.19880710715
Subject(s) - chemistry , diol , stereochemistry , epoxy , carotene , high performance liquid chromatography , chromatography , organic chemistry
( all‐ E )‐12′‐Apozeanthinol, Persicaxanthine, and Persicachromes Reexamination of the so‐called ‘persicaxanthins’ and ‘persicachromes’, the fluorescent and polar C 25 ‐apocarotenols from the flesh of cling peaches, led to the identification of the following components: (3 R )‐12′‐apo‐β‐carotene‐3,12′‐diol ( 3 ), (3 S ,5 R ,8 R , all‐ E )‐ and (3 S ,5 R ,8 S ,all‐ E )‐5,8‐epoxy‐5,8‐dihydro‐12′‐apo‐β‐carotene‐3,12′‐diols (4 and 5, resp.), (3 S ,5 R ,6 S ,all‐ E )‐5,6‐epoxy‐5,6‐dihydro‐l2′‐apo‐β‐carotene‐3,12′‐diol =persicaxanthin; ( 6 ), (3 S ,5 R ,6 S ,9 Z ,13′ Z )‐5,6‐dihydro‐12′apo‐β‐carotene‐3,12′‐diol ( 7 ; probable structure), (3 S ,5 R ,6 S ,15 Z )‐5,6‐epoxy‐5,6‐dihydro‐12′‐apo‐β‐carotene‐3,12′‐diol ( 8 ), and (3 S ,5 R ,6 S ,13 Z )‐5,6‐epoxy‐5,6‐dihydro‐12′‐apo‐β‐carotene‐3,12′‐diol ( 9 ). The ( Z )‐isomers 7 – 9 are very labile and, after HPLC separation, isomerized predominantly to the (all‐ E )‐isomer 6 .