We synthesized several vitamin E analogues containing oxygenated funct
ional 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 have specific functions other than the antioxidant functio
n. All the vitamin E analogues examined has antioxidant activity. hyl-
2-(4,8,12-trimethyltridecanyl)chroman]methanol (1d) and imethyl-2-(4,8
,12-trimethyltridecanyl)chroman-6-ol (4d) showed similar activity to a
lpha-tocopherol. (4,8,12-trimethyltridecanyl)chroman-8-carbaldehyde (2
d) and 2-(4,8,12-trimethyltridecanyl)chroman-8-carboxylic acid (3d) sh
owed weaker activity than alpha-tocopherol, but their duration of acti
on, especially that of 3d was considerably longer.