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Long-lasting Antioxidant Protection: A Regenerable BHA-Analogue
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry. (Lars Engman)
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2010 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 75, no 22, 7535-7541 p.Article in journal (Refereed) Published
Abstract [en]

Introduction of an octyltelluro group ortho to the phenolic moiety in 3-tert-butyl-4-hydroxyanisole (BHA) was found to significantly improve the antioxidant characteristics of the material. In contrast to BHA and the corresponding ortho-substituted octylthio- (9c) and octylseleno (9b) derivatives, the organotellurium 9a was regenerable when assayed for its capacity to inhibit azo-initiated peroxidation of linoleic acid in a chlorobenzene/water two-phase system containing N-acetylcysteine as a stoichiometric reducing agent, and peroxyl radicals were quenched more efficiently than with α-tocopherol. In the homogeneous phase, inhibition of styrene autoxidation occurred with a rate constant kinh as large as 1 × 107 M-1 s-1 but with a low (n = 0.4) stoichiometric factor. Evans-Polanij plots of log (kinh) versus BDE(O-H), which are usually linear for phenols with similar steric crowding reacting by H-atom transfer, revealed that compound 9a was more than 2 orders of magnitude more reactive than expected. Although further mechanistic investigations are needed, it seems that the ortho-arrangement of an alkyltelluro group and hydroxyl should be considered a privileged structure for phenolic antioxidants.

Place, publisher, year, edition, pages
2010. Vol. 75, no 22, 7535-7541 p.
National Category
Chemical Sciences
Research subject
Chemistry with specialization in Organic Chemistry
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URN: urn:nbn:se:uu:diva-133968DOI: 10.1021/jo101239cISI: 000284080300004PubMedID: 20973511OAI: oai:DiVA.org:uu-133968DiVA: diva2:371307
Available from: 2010-11-19 Created: 2010-11-19 Last updated: 2017-12-12Bibliographically approved

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