Synthesis and antiradical/antioxidant activities of caffeic acid phenethyl ester and its related propionic, acetic, and benzoic acid analogues

Molecules. 2012 Dec 10;17(12):14637-50. doi: 10.3390/molecules171214637.

Abstract

Caffeic acid phenethyl ester (CAPE) is a bioactive component isolated from propolis. A series of CAPE analogues was synthesized and their antiradical/antioxidant effects analyzed. The effect of the presence of the double bond and of the conjugated system on the antioxidant effect is evaluated with the analogues obtained from 3-(3,4-dihydroxyphenyl) propanoic acid. Those obtained from 2-(3,4-dihydroxyphenyl) acetic acid and 3,4-dihydroxybenzoic acid allow the evaluation of the effect of the presence of two carbons between the carbonyl and aromatic system.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetic Acid / chemistry
  • Antioxidants* / chemical synthesis
  • Antioxidants* / chemistry
  • Benzoic Acid / chemistry
  • Caffeic Acids* / chemical synthesis
  • Caffeic Acids* / chemistry
  • Carbon / chemistry
  • Lipid Peroxidation
  • Oxidation-Reduction
  • Phenylethyl Alcohol / analogs & derivatives*
  • Phenylethyl Alcohol / chemical synthesis
  • Phenylethyl Alcohol / chemistry
  • Propionates / chemistry
  • Propolis / chemistry*

Substances

  • Antioxidants
  • Caffeic Acids
  • Propionates
  • Carbon
  • Benzoic Acid
  • Propolis
  • caffeic acid phenethyl ester
  • propionic acid
  • Phenylethyl Alcohol
  • Acetic Acid