Enzymatic synthesis of vanillyl fatty acid esters from salmon oil in a solvent-free medium

Food Chem. 2025 Feb 1;464(Pt 2):141656. doi: 10.1016/j.foodchem.2024.141656. Epub 2024 Oct 18.

Abstract

This study hypothesizes that the solvent-free alcoholysis of oil recovered from salmon heads using vanillyl alcohol (VA) and immobilized lipase B can efficiently produce esters with enhanced stability and antioxidant properties. The objective was to investigate the selectivity and resulting ester profile, which may provide nutritional and functional advantages compared to supplementing oil with vanillyl alcohol. After 24 h, nearly complete conversion of vanillyl alcohol was achieved, leading to the production of various esters reflective of the oil's original fatty acid composition. The synthesis of esters like oleoyl and linolenoyl was favored over docosahexaenoyl and linoleoyl esters, influenced by fatty acid distribution and enzyme specificity, along with potential intra-molecular acyl transfer isomerization. The reaction medium demonstrated significant stability and antioxidant activity, highlighting the potential benefits of vanillyl esters over traditional supplementation methods. These findings suggest that the phenolic alcohol-based alcoholysis of fish oil offers a promising approach to generating stable, nutritionally valuable extracts with potent antioxidant capabilities.

Keywords: Antioxidant activity; Lipase-catalyzed transesterification; Oxidative stability; Phenolic lipids; Vanillyl alcohol.

MeSH terms

  • Animals
  • Antioxidants / chemistry
  • Benzyl Alcohols / chemistry
  • Biocatalysis
  • Enzymes, Immobilized / chemistry
  • Esterification
  • Esters* / chemistry
  • Fatty Acids* / chemistry
  • Fish Oils* / chemistry
  • Lipase* / chemistry
  • Lipase* / metabolism
  • Salmon*

Substances

  • Fish Oils
  • Esters
  • Lipase
  • Fatty Acids
  • salmon oil
  • Enzymes, Immobilized
  • vanillyl alcohol
  • Benzyl Alcohols
  • Antioxidants