The radical scavenging reactions of a vitamin
E
model compound,
2
,
2
,
5
,
7
, 8-pentamethylchroman-
6
-ol, with radicals from the Fe (II)-induced decomposition of a linoleic acid hydroperoxide, (
9
Z, 11
E
)-13-hydroperoxy-
9
, 11-octadecadienoic acid, were examined extensively. When Fe (II) was added to a mixture of the vitamin
E
model compound and the linoleic acid hydroperoxide in methanol, (
9
E
)-trans-12, 13-epoxy-erythro-11-, (
9
E
)-trans-12, 13-epoxy-threo-11-, (
9
Z)-trans-12, 13-epoxy-erythro-11-and (
9
Z)-trans-12, 13-epoxy-threo-11-(
2
,
2
,
5
,
7
, 8-pentamethylchromanoxy)-
9
-octadecenoic acids, and (
9
E
)-13-hydroxy-12-methoxy-11-(
2
,
2
,
5
,
7
, 8-pentamethylchromanoxy)-
9
-, (10
E
)-13-hydroxy-12-methoxy-
9
-(
2
,
2
,
5
,
7
, 8-pentamethylchromanoxy)-10-and (11
E
)-13-hydroxy-10-methoxy-
9
-(
2
,
2
,
5
,
7
, 8-pentamethylchromanoxy)-11-octadecenoic acids were obtained as main products. The hydroxymethoxy acids are presumed to be derived from the epoxy acids. A possible reaction pathway for the formation of the products is discussed.
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