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Antioxidant activity of oxidation products of α‐tocopherol and of its model compound 2,2,5,7,8‐pentamethyl‐6‐chromanol
Author(s) -
Suarna Cacang,
SouthwellKeely Peter T.
Publication year - 1991
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02543969
Subject(s) - antioxidant , chemistry , tocopherol , hydroxymethyl , stereochemistry , organic chemistry , medicinal chemistry , vitamin e
A variety of oxidation products (4–29) of α‐tocopherol, 1 and of its model compound, 2,2,5,7,8‐pentamethyl‐6‐chromanol (2) has been tested for antioxidant activity against autoxidizing safflower oil (ASO) and autoxidizing methyl linoleate (AML). The following compounds showed good antioxidant activity against both substrates: 5‐hydroxymethyl‐2,2,7,8‐tetramethyl‐6‐chromanol (4), 5‐(2,2,5,7,8‐pentamethyl‐6‐chromanoxy)methyl‐2,2,7,8‐tetramethyl‐6‐chromanol (15), 1,2‐ bis (2,2,7,8‐tetramethyl‐6‐chromanol‐5‐)ethane (16), 5‐ethoxymethyl‐7,8‐dimethyltocol (19), 5‐mthoxymethyl‐2,2,7,8‐tetramethyl‐6‐chromanol (21), 5‐ethoxymethyl‐2,2,7,8‐tetramethyl‐6‐chromanol (20), 5‐propoxymethyl‐2,2,7,8‐tetramethyl‐6‐chromanol (22), 5‐butoxymethyl‐2,2,7,8‐tetramethyl‐6‐chromanol (23), 5‐(2‐methyl‐1‐propoxy)methyl‐2,2,7,8‐tetramethyl‐6‐chromanol (24), 5‐(2‐methyl‐2‐propoxy)methyl‐2,2,7,8‐tetramethyl‐6‐chromanol (25), 5‐heptoxymethyl‐2,2,7,8‐tetramethyl‐6‐chromanol (26), 5‐undecoxymethyl‐2,2,7,8‐tetramethyl‐6‐chromanol (27), 5‐phytoxymethyl‐2,2,7,8‐tetramethyl‐6‐chromanol (28) and 5‐cholesteroxymethyl‐2,2,7,8‐tetramethyl‐6‐chromanol (29). 2,2,7,8‐Tetramethylchroman‐5,6‐dione (17) and 1,2‐ bis (2,2,7‐trimethylchroman‐5,6‐dione‐8‐)ethane (18) showed significant antioxidant activity against ASO but not against AML. If the corresponding oxidation products of 1 are formed in vivo it means that the antioxidant activity of 1 is not lost on oxidation. This may help to explain the outstanding capacity of 1 to protect cell membranes.