Formation of α-hydroxycarbonyl and α-dicarbonyl compounds during degradation of monosaccharides

Ondřej Novotný, Karel Cejpek and Jan Velíšek
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Ondřej Novotný: Department of Food Chemistry and Analysis, Faculty of Food and Biochemical Technology, Institute of Chemical Technology in Prague, Prague, Czech Republic
Karel Cejpek: Department of Food Chemistry and Analysis, Faculty of Food and Biochemical Technology, Institute of Chemical Technology in Prague, Prague, Czech Republic
Jan Velíšek: Department of Food Chemistry and Analysis, Faculty of Food and Biochemical Technology, Institute of Chemical Technology in Prague, Prague, Czech Republic

Czech Journal of Food Sciences, 2007, vol. 25, issue 3, 119-130

Abstract: The formation of α-hydroxycarbonyl and α-dicarbonyl compounds from monosaccharides (glucose, fructose, arabinose, glyceraldehyde, and 1,3-dihydroxyacetone) was studied in three different model systems comprising an aqueous and alkaline solution of potassium peroxodisulfate (K2S2O8), and a solution of sodium hydroxide, respectively. In total, six α-hydroxycarbonyl (in the form of O-ethyloximes) and six α-dicarbonyl compounds (as quinoxaline derivatives) were identified by GC/MS and quantified. Acetol, glycolaldehyde, 1,3-dihydroxyacetone, methylglyoxal, and glyoxal were the most abundant low molecular weight carbonyls. Within the model systems studied, the yield of α-hydroxycarbonyl and α-dicarbonyl compounds was 0.32-4.90% (n/n) and 0.35-9.81% (n/n), respectively. The yield of α-dicarbonyls was higher than that of α-hydroxycarbonyls only in aqueous solution of K2S2O8 and in the other two model systems an inverse ratio of these two carbonyl types was found. For the first time, ethylglyoxal was identified as a sugar degradation product and several mechanisms explaining its formation were proposed. The achieved data indicated that low molecular weight α-hydroxycarbonyl and α-dicarbonyl compounds are predominantly formed by a direct retro-aldol reaction and α- and β-dicarbonyl cleavage. It was evident that some compounds were produced from the sugar fragmentation products. Thus, isomerisation, reduction of dicarbonyls by formaldehyde (cross-Cannizzaro reaction), and mutual disproportionation are possible reaction pathways participating in the formation of α-hydroxycarbonyl compounds. Oxidation and disproportionation of α-hydroxycarbonyl precursors as well as the aldol condensation of low molecular weight carbonyl species (followed by subsequent reactions) play an important role in the formation of several α-dicarbonyl compounds.

Keywords: monosaccharides; α -hydroxycarbonyl compounds; -dicarbonyl compounds; retro-aldol reaction; peroxodisulfate; acetol; 1; 3-dihydroxyacetone; glyceraldehyde; glycolaldehyde; acetoin; 1-hydroxybutan-2-one; lactaldehyde; glyoxal; methylglyoxal; ethylglyoxal; butane-2; 3-dione; 1-hydroxybutane-2; pentane-2 (search for similar items in EconPapers)
Date: 2007
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Persistent link: https://EconPapers.repec.org/RePEc:caa:jnlcjf:v:25:y:2007:i:3:id:740-cjfs

DOI: 10.17221/740-CJFS

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