Antioxidant Capacity of 1-Deoxy-D-erythro-hexo-2,3-diulose and D-arabino-Hexo-2-ulose

The antioxidant capacity of two 1,2-dicarbonyl compounds, 1-deoxy-D-erythro-hexo-2,3-diulose (1-deoxyglucosone) and D-arabino-hexo-2-ulose (D-glucosone), was investigated. Both compounds are key intermediates of the Mail lard reaction, and both possess a reductone-like structure. The reductive potential of the reductones was measured with the trolox equivalent antioxidant capacity (TEAC) assay and the Folin-Ciocalteu reagent (FCR) assay. Their antioxidant capacity set them apart from their precursors and other typical Mail lard reaction products. Using electron paramagnetic resonance (EPR) spectroscopy, the special radical scavenging behavior of 1-deoxyglucosone and D-glucosone was measured. Both exhibited a slow, but constant, scavenging ability over the course of several hours, even days. It was postulated that this characteristic behavior is caused by the isomeric composition and the transformation to the particular antioxidant form. Reaction mixtures of 1-deoxyglucosone showed a correlation between the decrease of antioxidant properties and the decomposition of 1-deoxyglucosone.