The Use of Aminoguanidine To Trap and Measure Dicarbonyl Intermediates Produced During the Maillard Reaction

Aminoguanidine, an inhibitor of the Maillard reaction functions by rapidly reacting with dicarbonyl intermediates, which are produced from Amadori compounds, converting them into stable 5- and 6- substituted 3-aminotriazine derivatives. The latter can be easily identified and quantitated (by GLC), thus allowing an assessment to be made, not only of the rate of degradation of Amadori compounds to dicarbonyl intermediates, but the type of intermediate that is formed in the reaction as well. Using a number of Amadori compounds prepared from glucose and amino acids, the results show that two different dicarbonyl compounds are produced in the reaction, namely the expected 3-deoxy-1,2-dicarbonyl derivative, but also the 1-deoxy-2,3-dicarbonyl intermediate. The latter represents an intermediate in the formation of a number of methyl furanones which are food flavor and aroma constituents.