State Key Laboratory of Food Nutrition and Safety, Key Laboratory of Food Nutrition and Safety, Ministry of Education, College of Food Science and Engineering, Tianjin University of Science and Technology, Tianjin 300457, China.
State Key Laboratory of Food Nutrition and Safety, Key Laboratory of Food Nutrition and Safety, Ministry of Education, College of Food Science and Engineering, Tianjin University of Science and Technology, Tianjin 300457, China.
Food Res Int. 2024 Jun;186:114372. doi: 10.1016/j.foodres.2024.114372. Epub 2024 Apr 21.
The oxidation and degradation of fats lead to a decrease in the nutritional value of food and pose safety concerns. Saturated fatty acids also hold a significant position in the field of lipid oxidation. In this study, the oxidation products of methyl palmitate were investigated by using gas chromatography mass spectrometry (GC-MS). Seven monohydroperoxides and 72 secondary oxidation products were detected. Combined with density functional theory (DFT) calculations, the formation mechanisms of oxidation products can be summarized into four stages. The initial stage involved the formation of monohydroperoxides and alkanes, followed by the subsequent stage involving methyl x-oxo(hydroxy)hexadecanoates. The third stage involved the formation of methyl ketones, carboxylic acids, and aldehydes, while the final stage involved lactones. Meanwhile, methyl ketones were the most abundant oxidation product, approximately 25 times more abundant than aldehydes; the calculated results agreed well with the experimental results. The establishment of a comprehensive thermal oxidation mechanism for palmitic acid provided a new foundation for future lipid oxidation analyses.
脂肪的氧化和降解会导致食物营养价值降低,并引发安全问题。饱和脂肪酸在脂质氧化领域也占有重要地位。在本研究中,使用气相色谱-质谱联用(GC-MS)技术研究了棕榈酸甲酯的氧化产物。共检测到 7 种单氢过氧化物和 72 种次级氧化产物。结合密度泛函理论(DFT)计算,可以将氧化产物的形成机制总结为四个阶段。初始阶段涉及单氢过氧化物和烷烃的形成,随后是随后的阶段,涉及甲基 x-氧(羟)十六烷酸酯。第三阶段涉及甲基酮、羧酸和醛的形成,而最后阶段涉及内酯。同时,甲基酮是最丰富的氧化产物,大约是醛的 25 倍;计算结果与实验结果吻合较好。建立了棕榈酸的综合热氧化机制,为今后的脂质氧化分析提供了新的基础。