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Autoxidation of synthetic isomers of triacylglycerol containing eicosapentaenoic acid

  • Published:
Journal of the American Oil Chemists' Society

Abstract

Several triacylglycerols (TAG) that contained eicosapentaenoic acid (EPA) were chemically synthesized and stored at 25°C to assess the influence of TAG structure on oxidative stability and formation of oxidation products. Oxidative stability was evaluated by oxygen consumption during storage of the TAG. Autoxidation products of TAG were analyzed by high-performance liquid chromatography (HPLC) and liquid chromatography-mass spectrometry (LC-MS). Results showed that a 2:1 (mole/mole) mixture of trieicosapentaenoylglycerol (EEE) and tripalmitoylglycerol (PPP) was most susceptible to autoxidation. The oxidative stability of TAG that contained EPA and palmitic acid was negatively correlated with the moles of EPA in a single TAG molecule. When TAG with one EPA and two other fatty acids were oxidized, chainlength of constituent fatty acids hardly affected the oxidative stability of EPA-containing TAG molecules, except for stearic acid. HPLC and LC-MS analyses showed that monohydroperoxides were major oxidation products regardless of type of TAG. Bis- and tris-hydroperoxides were formed during autoxidation of EEE and dieicos-apentaenoylpalmitoylglycerol. Monohydroperoxy epidioxides were found in all autoxidized TAG. These observations suggested that TAG structure affected the oxidation of TAG with highly unsaturated fatty acids.

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Authors and Affiliations

  1. Department of Applied Biological Chemistry, Faculty of Agriculture, Tohoku University, 1-1 Tsutsumidori-Amamiyamachi, Aoba, 981, Sendai, Japan

    Yasushi Endo, Sanae Hoshizaki & Kenshiro Fujimoto

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  1. Yasushi Endo
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  2. Sanae Hoshizaki
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  3. Kenshiro Fujimoto
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Endo, Y., Hoshizaki, S. & Fujimoto, K. Autoxidation of synthetic isomers of triacylglycerol containing eicosapentaenoic acid. J Amer Oil Chem Soc 74, 543–548 (1997). https://doi.org/10.1007/s11746-997-0178-x

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  • DOI: https://doi.org/10.1007/s11746-997-0178-x

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