Premium
Synthesis of Vitamin E Analogues: Possible Active Forms of Vitamin E
Author(s) -
Fujishima Toshie,
Kagechika Hiroyuki,
Shudo Koichi
Publication year - 1996
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19963290106
Subject(s) - chemistry , antioxidant , vitamin e , biological activity , vitamin , stereochemistry , methanol , tocopherol , vitamin c , biochemistry , organic chemistry , in vitro
Abstract We synthesized several vitamin E analogues containing oxygenated functional groups in place of the 8‐methyl group which is common to all the natural vitamin E congeners, based on the hypothesis that the methyl group might be metabolically oxidized to produce active forms which might have specific functions other than the antioxidant function. All the vitamin E analogues examined had antioxidant activity. 8‐[6‐Hydroxy‐2,5,7‐trimethyl]‐2‐(4,8,12‐trimethyltridecanyl)chroman'methanol ( 1d ) and 2,5,7‐trimethyl‐2‐(4,8,12‐trimethyltridecanyl)chroman‐6‐ol ( 4d ) showed similar activity to α‐tocopherol. 6‐Hydroxy‐2,5,7‐trimethyl‐2‐(4,8,12‐trimethyltridecanyl) chroman‐8‐carbaldehyde ( 2d ) and 6‐hydroxy‐2,5,7‐trimethyl‐2‐(4,8,12‐trimethyltridecanyl)chroman‐8‐carboxylic acid ( 3d ) showed weaker activity than α‐tocopherol, but their duration of action, especially that of 3d was considerably longer.