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Confirmation of the Absolute (3R,3′S,6′R)-Configuration of (all-E)-3′-Epilutein

✍ Scribed by Péter Molnár; József Deli; Erzsébet Ősz; Ferenc Zsila; Miklós Simonyi; Gyula Tóth

Publisher
John Wiley and Sons
Year
2004
Tongue
German
Weight
242 KB
Volume
87
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Circular dichroism (CD) spectroscopy was used to distinguish between the isomeric (all‐E)‐configured 3′‐epilutein (2) and 6′‐epilutein (8) to establish the absolute configuration of epilutein samples of different (natural and semisynthetic) origin, including samples of 2 obtained from thermally processed sorrel. Thus, the CD data of lutein (1) and epilutein samples (2) were compared. Our results unambiguously confirmed the (3__R__,3′S,6′R)‐configuration of all epilutein samples. Compound 2 was thoroughly characterized, and its ^13^C‐NMR data are published herewith for the first time.

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A method is described for the qualitative and quantitative determination of configurational isomers of zeaxanthin (= 3,3' -dihydroxy-P, p -carotene) and lutein (= 3 3 -dihydroxya-carotene). It is based on the reaction of these zeaxanthin and lutein isomers with (S)-(+)-e-(l -naphthyl) ethyl isocyana