"Cut-off" effect of antioxidants and/or probes of variable lipophilicity in microheterogeneous media

Food Chem. 2016 Sep 1:206:119-23. doi: 10.1016/j.foodchem.2016.03.024. Epub 2016 Mar 9.

Abstract

The activities of two hydrophilic (ascorbic acid and Trolox) and two hydrophobic (α-tocopherol and BHT) antioxidants were measured by reaction with a series of 4-alkanoyloxyTEMPO radical probes 1 in buffered (pH 7), aqueous, micellar solutions of reduced Triton-X 100. In all cases, a cut-off effect was observed, in line with previous observations of the same effect for the partitioning of probe series 1 in this medium. These results support an interpretation of the cut-off effect in food emulsions, based on the "amphiphobic" nature of either the antioxidants or probes: competition between two molecular moieties, for the micellar hydrophobic core, tends to expose a reacting fragment differently to a more hydrophilic microenvironment, as the probe or antioxidant hydrophobicity increases.

Keywords: 4-AlkanoyloxyTEMPO; Antioxidant activity; Ascorbate; BHT; EPR; Hydrophobicity; Micelle; Trolox; α-Tocopherol.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antioxidants / chemistry*
  • Ascorbic Acid / chemistry
  • Butylated Hydroxytoluene / chemistry
  • Chromans / chemistry
  • Hydrophobic and Hydrophilic Interactions*
  • Micelles
  • Oxidation-Reduction
  • alpha-Tocopherol / chemistry

Substances

  • Antioxidants
  • Chromans
  • Micelles
  • Butylated Hydroxytoluene
  • alpha-Tocopherol
  • Ascorbic Acid
  • 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid