3-mercaptohexanol and caffeic-acid

In the present study, the reaction between 1-hydroxyethyl radicals (1-HER) and various wine-related phenolics and thiols, including gallic acid, caffeic acid, ferulic acid, 3-mercaptohexan-1-ol (3MH), cysteine (Cys), and glutathione (GSH), was studied using competitive spin trapping with electron paramagnetic resonance (EPR) and mass spectrometry. Previous studies have reported several important reactions occurring between quinones and other wine components, but the fate of 1-HER within the context of wine oxidation is less understood. Furthermore, the ability of these compounds to prevent formation of acetaldehyde, a known nonenzymatic oxidation product of ethanol, was measured. The hydroxycinnamic acids and thiol compounds tested at 5 mM concentrations significantly inhibited spin adduct formation, indicating their reactivity toward 1-HER. In addition, we confirm that loss of 3MH under model wine conditions is due to quinone trapping as well as 1-HER-induced oxidation.

Topics: Caffeic Acids; Coumaric Acids; Cysteine; Electron Spin Resonance Spectroscopy; Ethanol; Gallic Acid; Glutathione; Mass Spectrometry; Oxidation-Reduction; Phenols; Sulfhydryl Compounds; Wine