Thiyl radical-catalyzed isomerization of oils: An entry to the trans lipid library

Abstract

The unsaturated fatty acyl moieties of TAG present in natural oils of borage, olive, and rice were converted to their corresponding geometrical trans isomers by thiyl radical-catalyzed isomerization. Thiyl radicals were generated from 2-mercaptoethanol under photolytic or thermal conditions. A relevant feature of this method is the absence of double-bond shifts, so that no positional trans isomers or conjugated polyenes are formed. Oils obtained after the isomerization were winterized to further increase their trans fatty acid content. Methanolysis and hydrolysis of the trans oil mixtures using an enzymatic method (lipase B from Candida antarctica) gave good conversions to the corresponding trans FAME and fatty acids, respectively. These results are relevant for the studies of lipid isomerism and trans fatty acid recognition, which is a growing concern in biochemistry and nutrition, and open new perspectives for the synthesis of glycerides and studies of their structure-activity relationships.

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Correspondence to Carla Ferreri or Chryssostomos Chatgilialoglu.

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Samadi, A., Andreu, I., Ferreri, C. et al. Thiyl radical-catalyzed isomerization of oils: An entry to the trans lipid library. J Amer Oil Chem Soc 81, 753–758 (2004). https://doi.org/10.1007/s11746-004-0974-8

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Key Words

  • Geometrical isomerization
  • lipase
  • thiyl radicals
  • trans fatty acids
  • trans oils