Analysis of the transformation products of dehydro-L-ascorbic acid by ion-pairing high-performance liquid chromatography

Anal Biochem. 1993 Oct;214(1):38-44. doi: 10.1006/abio.1993.1453.

Abstract

Dehydro-L-ascorbic acid, the oxidation form of L-ascorbic acid, converts nonenzymatically to a variety of transformation products depending upon the incubating conditions. These products, called the ascorbate cascade, possess different absorption spectra and reducing activities. Ion-pairing high-performance liquid chromatography with multiwavelength uv absorption and amperometric electrochemical detection has proven to be a useful technique for the analysis of these products. Separation and characterization in the present investigations reveal three kinds of transformation products: the polymerized intermediates of browning reaction, the reductant possessing an absorption maximum at 345 nm as the six-carbon compound, and erythro-L-ascorbic acid, 2-furoic acid, 3-hydroxy-2-pyrone, 5-methyl-3,4-dihydroxytetrone, reductic acid, and furfural as the five-carbon compound. These products possess an absorption maximum above 240 nm, and most of them are electrochemically active reducing compounds which are derived from nonreducing dehydro-L-ascorbic acid through the processes of delactonization, decarboxylation, and intramolecular rearrangement.

MeSH terms

  • Chromatography, High Pressure Liquid / methods
  • Chromatography, Ion Exchange / methods
  • Dehydroascorbic Acid / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Oxidation-Reduction

Substances

  • Dehydroascorbic Acid