Quantitative assessment of epoxide formation in oil and mayonnaise by 1H-13C HSQC NMR spectroscopy

Vincent J.P. Boerkamp, Donny W.H. Merkx, Jianli Wang, Jean Paul Vincken, Marie Hennebelle*, John P.M. van Duynhoven

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

13 Citations (Scopus)


Lipid oxidation is detrimental for the quality of oil-based foods. Historically, lipid oxidation research focussed on hydroperoxides and aldehydes, but a third class, the epoxides, have been proposed to resolve observed mechanistic anomalies. Here, we developed a 2D 1H-13C HSQC NMR spectroscopic method to quantify epoxides in food in a reproducible (relative standard deviation ≤11.6 %) and sensitive (LoQ 0.62 mmol/kg oil) manner. Lipid hydroperoxides, aldehydes, and epoxides generated in rapeseed oil and mayonnaise were quantified over time by NMR. Epoxides accounted at most for 10–40 % of the products. They were formed after hydroperoxide accumulation, most likely primarily via alkoxyl radical intermediates, which limits their potential as an early oxidation marker. As 99 % and ∼60 % of the epoxide signal intensities were assigned in a fatty acid and sub-structure specific manner, respectively, our quantitative HSQC method will enable unravelling and quantitative modelling of lipid oxidation mechanisms.

Original languageEnglish
Article number133145
JournalFood Chemistry
Publication statusPublished - 1 Oct 2022


  • Bulk oil
  • Epoxides
  • Lipid oxidation
  • Mayonnaise
  • Mechanistic insight


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