Epoxyalkenal-trapping ability of phenolic compounds

Area of Science:

• Food Chemistry
• Organic Chemistry
• Food Safety

Background:

• Lipid oxidation generates carbonyl compounds that negatively impact food quality and safety through reactions with amines.
• Phenolic compounds show potential in preventing these reactions, but their carbonyl-trapping mechanisms are not fully understood.

Purpose of the Study:

• To investigate the reaction mechanisms between specific epoxyalkenals and phenolic compounds.
• To characterize the adducts formed and understand how phenolics deactivate reactive carbonyls.

Main Methods:

• Studied reactions between 4,5-epoxy-2-hexenal, 4,5-epoxy-2-heptenal, and 4,5-epoxy-2-decenal with 2-methylresorcinol and 2,5-dimethylresorcinol.
• Isolated and characterized reaction products using 1D and 2D Nuclear Magnetic Resonance (NMR) and Mass Spectrometry (MS).

Main Results:

• Identified diverse tetrahydrofurochromenediols and tetrahydropyranozbenzofurandiols as reaction products.
• Elucidated a reaction pathway involving epoxide ring-opening by phenolic hydroxyl groups, followed by addition of an aromatic carbon to the epoxyalkenal's double bond.
• Demonstrated that these reactions effectively deactivate the reactive groups of epoxyalkenals.

Conclusions:

• The reaction between phenolics and epoxyalkenals forms adducts that significantly reduce the epoxyalkenals' ability to react with amines.
• This provides mechanistic insight into how phenolics can mitigate lipid oxidation-induced food quality deterioration.