Journal of Nutritional Science and Vitaminology
Online ISSN : 1881-7742
Print ISSN : 0301-4800
ISSN-L : 0301-4800
Thermal Stereoisomerization of All-(E)-β-Carotene: (Z)-β-Carotenes and Electrocyclized β-Carotenes
月田 潔斎木 加代子
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1983 年 29 巻 2 号 p. 111-122

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Thermal isomerization of synthetic all-(E)-β-carotene yielded a multi-component mixture composed of more than sixteen (Z)-β-carotenes and two thermo-cyclized isomers. They were separated and purified by high-performance liquid chromatography. Ten of these were characterized by spectroscopic methods as four mono-(Z)-, five di-(Z)-, and one tri-(Z)-β-carotenes; the 7-(Z)-, 9-(Z)-, 13-(Z)-, 15-(Z)-, 9.13-(Z)-, 9.15-(Z)-, 9.13'-(Z)-, 13.15-(Z)-, 7.13'-(Z)-, and 9.9'.13-(Z)-isomers were included. Stereochemistry of six additional (Z)-isomers obtained is, as yet, unknown, though one of them might have the 9.9'-(Z)-geometry in the molecule. This is the first report on the formation and identification of the ‘sterically hindered’ 7-(Z)-isomers as well as the (5→10)-thermo-cyclized products in the field of alicyclic carotenoids
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