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Autoxidation of synthetic isomers of triacylglycerol containing eicosapentaenoic acid
Author(s) -
Endo Yasushi,
Hoshizaki Sanae,
Fujimoto Kenshiro
Publication year - 1997
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/s11746-997-0178-x
Subject(s) - autoxidation , chemistry , eicosapentaenoic acid , high performance liquid chromatography , chromatography , fatty acid , organic chemistry , oxidative phosphorylation , palmitic acid , stearic acid , polyunsaturated fatty acid , biochemistry
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.