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Oxidative stability of DHA phenolic ester.

Mohamed H H Roby1, Vanessa C De Castro2, Brenda N Targino2

  • 1Université de Lorraine, Laboratoire Ingénierie des Biomolécules (LIBio), 2 av. de la Forêt d'Haye, TSA 40602, 54518 Vandoeuvre Cedex, France; Fayoum University, Food Science and Technology Dept., Faculty of Agriculture, 63514 Fayoum, Egypt.

Food Chemistry
|September 20, 2014
PubMed
Summary

Docosahexaenoic acid vanillyl ester (DHA-VE) shows enhanced oxidative stability compared to its precursor, docosahexaenoic acid ethyl ester (DHA-EE). This stabilization offers potential for DHA-VE as a functional ingredient.

Keywords:
DHA and vanillyl alcoholEnzymatic esterificationFTIR spectroscopy omega-3LipaseOxidationOxidative stabilityPUFA

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Area of Science:

  • Lipid chemistry
  • Enzymatic synthesis
  • Food science

Background:

  • Docosahexaenoic acid (DHA) is an omega-3 fatty acid crucial for health but prone to oxidation.
  • Developing stable DHA derivatives is essential for functional food applications.
  • Current DHA formulations often suffer from limited shelf-life due to oxidation.

Purpose of the Study:

  • To synthesize docosahexaenoic acid vanillyl ester (DHA-VE) using a green enzymatic process.
  • To evaluate and compare the oxidative stability of DHA-VE and a DHA-VE/DHA-EE mixture against DHA-EE.
  • To explore the potential of stabilized DHA-VE as a functional ingredient.

Main Methods:

  • Solvent-free enzymatic alcoholysis using Candida antarctica lipase B to synthesize DHA-VE from DHA-EE and vanillyl alcohol.
  • Comparative oxidative stability assessment under various storage conditions (temperature, time).
  • Monitoring oxidation via conjugated diene analysis and Fourier-transform infrared (FTIR) spectroscopy.

Main Results:

  • DHA-EE exhibited rapid oxidation under all tested conditions.
  • DHA-VE and the crude reaction medium (45% DHA-VE, 55% DHA-EE) demonstrated significantly improved oxidative stability.
  • The vanillyl alcohol moiety effectively protected DHA from oxidation, irrespective of storage parameters.

Conclusions:

  • Enzymatic synthesis of DHA-VE provides a stable alternative to DHA-EE.
  • Grafting vanillyl alcohol onto DHA is a potent strategy for enhancing oxidative resistance.
  • DHA-VE and the crude reaction medium possess considerable potential as stable functional ingredients in food products.