Mechanisms of the Formation of Nonvolatile and Volatile Oxidation Products from Methyl Linoleic Acid at High Temperatures

J Agric Food Chem. 2024 Jan 10;72(1):704-714. doi: 10.1021/acs.jafc.3c04405. Epub 2023 Dec 22.

Abstract

The impact of the oxidation of linoleic acid cannot be overlooked in daily food consumption. This study used gas chromatography-mass spectrometry (GC-MS) to identify both nonvolatile oxidation products and volatile oxidation products of methyl linoleic acid at 180 °C and density function theory to investigate oxidation mechanisms. An analysis of nonvolatile oxidation products revealed the presence of three primary oxidation products. The three primary oxidation products were identified as hydroperoxides, peroxide-linked dimers, and heterocyclic compounds in a ratio of 2.70:1:3.69 (mmol/mmol/mmol). The volatile components of secondary oxidation products were found including aldehydes (40.77%), alkanes (19.89%), alcohols (9.02%), furans (6.11%), epoxides (0.46%), and acids (2.50%). DFT calculation proved that the secondary oxidation products mainly came from peroxides (77%). Finally, we look forward to our research contributing positively to lipid autoxidation and human health.

Keywords: GC-MS; density function theory; methyl linoleic acid; nonvolatile oxidation products; oxidation mechanisms; volatile oxidation products.

MeSH terms

  • Aldehydes* / chemistry
  • Gas Chromatography-Mass Spectrometry
  • Humans
  • Linoleic Acid*
  • Linoleic Acids
  • Oxidation-Reduction
  • Temperature

Substances

  • Linoleic Acid
  • Aldehydes
  • Linoleic Acids