Antioxidant activities of vitamin E analogues in water and a Kamlet - Taft β-value for water

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DOIResolve DOI: http://doi.org/10.1021/ja954030r
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TypeArticle
Journal titleJournal of the American Chemical Society
ISSN0002-7863
Volume118
Issue15
Pages35453549; # of pages: 5
Subjectalpha tocopherol derivative; trolox c; antioxidant activity; article; controlled study; in vitro study
AbstractRate constants for hydrogen atom abstraction from two water-soluble α-tocopherol (α-TOH, vitamin E) analogues by tert-butoxyl radicals have been measured at room temperature in four solvents, including water. The results imply that H-atom abstraction from α-TOH is 3.9 times slower in water than in benzene and yield a 'reliable' Kamlet-Taft β solvent parameter for water of 0.31. Literature rate constants for H-atom abstraction by peroxyl radicals from α-TOH in SDS micelles and in phospholipid micelles are, respectively, about 100 and 1000 times lower than in styrene. Since only a small fraction of the observed rate diminution can be attributed to hydrogen bonding of α-TOH to water it is concluded that in these heterogeneous systems much of the α-TOH is physically inaccessible to the attacking radicals. Whether this is also true for α-TOH in the biological membranes in living animals remains to be determined.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada (NRC-CNRC)
Peer reviewedYes
NPARC number21276501
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Record identifier496231f8-1ffe-47b8-857d-5b9343adb5d0
Record created2015-10-13
Record modified2016-05-09
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