Molecular formation mechanism of trans linolenic acid in thermally induced alpha-linolenic acid

文献类型： 外文期刊

第一作者： Guo, Qin

作者： Guo, Qin;Li, Tian;Qu, Yang;Wang, Xinping;Liu, Li;Liu, Hongzhi;Wang, Qiang;Li, Tian;Qu, Yang;Wang, Xinping

作者机构：

关键词： alpha-Linolenic acid; Trans fatty acids; Heating; Mechanism; Density functional theory

期刊名称：LWT-FOOD SCIENCE AND TECHNOLOGY （ 影响因子：4.952； 五年影响因子：5.383 ）

ISSN： 0023-6438

年卷期： 2020 年 130 卷

页码：

收录情况： SCI

摘要： The isomerization mechanism of thermally induced alpha-linolenic acid (C18:3-9c,12c,15c) was investigated using a combination of experimental and computational studies. C18:3-9c,12c,15c in linseed oil and trilinolenin was heated at 180, 240, and 260 degrees C for 4 and 8 h and then analyzed by GC-MS. Mono-trans isomers easily formed from C18:3-9c,12c,15c, and then became double- and triple-trans isomers in heated linseed oil and trilinolenin. Six pathways of C18:3-9c,12c,15c isomerization via proton transfer were proposed and clarified. The hydrogen in the C9, C12, and C16 of the double bonds in C18:3-9c,12c,15c more favorably transferred to C10, C13, and C15, respectively, where the C9-H9 transfer occurred more quickly than C12-H12 and C16-H16 during isomerization. The formation of the mono-trans isomers was slower than the double- and triple-trans isomers, and the activation energies of the transition and rotate-transition states of the mono-trans isomers were the key factors influencing the formation of trans C18:3 isomers. Density functional theory calculations demonstrated the experimental data obtained was consistent with the proposed proton transfer isomerization mechanism.

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