Formation of Phenolic Compounds from d-Galacturonic Acid

J Agric Food Chem. 2018 Oct 31;66(43):11407-11413. doi: 10.1021/acs.jafc.8b04158. Epub 2018 Oct 18.

Abstract

Aqueous d-galacturonic acid (d-GalA) model systems treated at 130 °C at different pH values show an intense color formation, whereas other reducing sugars, such as d-galactose (d-Gal), scarcely react. GC-MS measurements revealed the presence of several phenolic compounds: e.g., 3,8-dihydroxy-2-methyl-4 H-chromen-4-one (chromone) and 2,3-dihydroxybenzaldehyde (2,3-DHBA). These phenolic compounds, especially 2,3-DHBA, possess an intense browning potential and cannot be found within heated model solutions of reducing sugars. Investigations regarding the formation of these substances show that α-ketoglutaraldehyde plays an important role as an intermediate product. In addition, MS analysis of model systems of norfuraneol in combination with 2,3-DHBA showed the formation of oligomers that could also be detected in d-GalA model systems, leading to the assumption that, in addition to reductic acid, these compounds are jointly responsible for the strong color formation during the heat treatment of d-GalA.

Keywords: 2,3-dihydroxybenzaldehyde; 3,8 dihydroxy-2-methyl-4H-chromen-4-one; catechol; d-galactose, furfural; d-galacturonic acid; methylcatechol; pectin; polygalacturonic acid; polyphenol; α-ketoglutaraldehyde.

MeSH terms

  • Benzaldehydes / chemistry
  • Catechols / chemistry
  • Food Handling
  • Gas Chromatography-Mass Spectrometry
  • Hexuronic Acids / chemistry*
  • Hot Temperature
  • Polyphenols / chemistry*
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

Substances

  • Benzaldehydes
  • Catechols
  • Hexuronic Acids
  • Polyphenols
  • 2,3-dihydroxybenzaldehyde
  • galacturonic acid