PMID: 11312840Apr 21, 2001Paper

In vitro test for the effectiveness of antioxidants as inhibitors of thiyl radical-induced reactions with unsaturated fatty acids

Journal of Agricultural and Food Chemistry
E Klein, N Weber

Abstract

Attacks of thiyl radicals on the double bonds of unsaturated fatty acids lead to stereomutation (cis-, trans-isomerization without double-bond migration) and addition reactions (thioether formation). On the basis of these findings, an in vitro test system has been developed which allows the study of the effectiveness of specific antioxidants in preventing thiyl radical-induced attacks on unsaturated fatty acids. The test involves thermal treatment of a mixture of oleic (cis-9-octadecenoic) acid and 1-tetradecanethiol with the antioxidant, followed by measurement of the extent of formation of the products of stereomutation and addition (i.e., elaidic (trans-9-octadecenoic) acid and isomeric 9(10)-S-tetradecylstearic acids, respectively) by gas chromatography of their methyl esters as a function of antioxidant concentration. Antioxidants such as octyl gallate, ascorbic acid 6-O-palmitate, ubiquinone 50 (coenzyme Q(10)), rac-alpha-tocopherol, and 2,6-di-tert-butyl-4-methylphenol (BHT) were tested for their ability to protect the >C=C< double bond of oleic acid against attacks of thiyl radicals generated from 1-tetradecanethiol by heating. The results show that octyl gallate, ascorbic acid 6-O-palmitate and, to some extent, ubiquin...Continue Reading

Citations

Nov 15, 2006·Applied Microbiology and Biotechnology·E FehlingK Vosmann
Dec 19, 2002·Free Radical Biology & Medicine·Chryssostomos ChatgilialogluLaura Landi
Jan 5, 2014·Chemical Reviews·Fabrice DénèsPhilippe Renaud
Aug 2, 2011·European Journal of Medicinal Chemistry·Stephan BraunArmin Buschauer
Jun 28, 2011·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·Lídia MendesMárcia Carvalho
Oct 28, 2016·Journal of Materials Science. Materials in Medicine·Paulo Emilio FeuserPedro H Hermes de Araújo
Feb 6, 2019·International Journal of Molecular Sciences·Andrea FratterFederico Benetti
Feb 5, 2011·Journal of Agricultural and Food Chemistry·Wei-Lun HungLucy Sun Hwang
Feb 17, 2005·Journal of Agricultural and Food Chemistry·Nikolai M KocherginskyAlex I Smirnov
May 13, 2004·Journal of Agricultural and Food Chemistry·Tae Joung HaIsao Kubo

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