The Synthesis and Antioxidant Profile of all-rac-α-Selenotocopherol
2006 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 71, no 3, 1033-1038 p.Article in journal (Refereed) Published
al-rac-a-Selenotocopherol (6c) has been synthesized in 11 steps in 6.6% total yield. Key steps include chloromethylation to approach the persubstituted aromatic 9b and cyclization of alcohol precursor 10 by radical homolytic substitution at selenium to form the selenotocopherol heterocycle. Determination of the OH bond dissociation enthalpy (BDE) of 6c by electron paramagnetic resonance (EPR) equilibration techniques gave a value of 78.1 + 0.3 kcal mol -1, approximately 1 kcal mol-1 higher than that of a-tocopherol. Kinetic studies performed by measuring oxygen uptake of the induced oxidant of styrene in the presence of an antioxidant showed that selenotocopherol (6c) was a slightly poorer inhibitor than a-tocopherol, in agreement with the BDE values. In contrast to simpler selenotocopherol analogues, 6c was not regenerable in teh presence of a stoichiometric coreductant in two-phase lipid peroxidation model.
Place, publisher, year, edition, pages
2006. Vol. 71, no 3, 1033-1038 p.
IdentifiersURN: urn:nbn:se:uu:diva-93799DOI: 10.1021/jo052133eOAI: oai:DiVA.org:uu-93799DiVA: diva2:167391