Biomimetic synthesis and antioxidant evaluation of 3,4-DHPEA-EDA [2-(3,4-hydroxyphenyl) ethyl (3S,4E)-4-formyl-3-(2-oxoethyl)hex-4-enoate]

Food Chem. 2014 Nov 1:162:89-93. doi: 10.1016/j.foodchem.2014.04.015. Epub 2014 Apr 13.

Abstract

Phenolic compounds present in extra virgin olive oil have attracted considerable recent attention. Many of them, show specific anti-inflammatory and anti-tumor activities. In this work we describe the biomimetic synthesis of 3,4-DHPEA-EDA [2-(3,4-hydroxyphenyl) ethyl (3S,4E)-4-formyl-3-(2-oxoethyl)hex-4-enoate], starting from natural demethyloleuropein present in olive tissues. A comparison between 3,4-DHPEA-EDA (6) and oleuropein (1), oleuropein aglycone (4) and hydroxytyrosol ORACFL values was undertaken.

Keywords: 3,4-DHPEA-EDA; Anti-inflammatory; Demethyloleuropein; Lanthanoid triflates; Lewis acid catalyst.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Inflammatory Agents
  • Antioxidants / chemistry*
  • Biomimetics / methods*
  • Humans
  • Molecular Structure
  • Olive Oil
  • Phenols / chemistry*
  • Plant Oils / chemistry*
  • Pyrans / chemistry*

Substances

  • 3,4-dihydroxyphenylethanol-elenolic acid dialdehyde
  • Anti-Inflammatory Agents
  • Antioxidants
  • Olive Oil
  • Phenols
  • Plant Oils
  • Pyrans