The Effect of pH on the Formation of Furfural Compounds in the Glucose and Fructose with Amino Acid Enantiomers in Maillard Reaction

  • Kim, Ji-Sang (Department of Food and Nutrition, Kyung Hee University) ;
  • Lee, Young-Soon (Department of Food and Nutrition, Kyung Hee University)
  • Published : 2008.03.31


This study was conducted to investigate the effect of pH on the formation of furfural compounds from glucose and fructose reacting with amino acid enantiomers in the Maillard reaction. Hydroxymethylfurfural (HMF) content was highest at pH 4.0, and decreased with increasing pH. HMF was significantly higher in glucose-based systems than fructose-based systems. Furfuryl alcohol (FFA) and 5-methyl-2-furaldehyde (MF) were not increased with increasing pH, and only small amounts were formed. In addition, 2-furaldehyde (F) was found to increase in the systems, as pH increased. However, the content was small and variable. 2,5-Dimethyl-4-hydroxy-3(2H)-furanone (DMHF) was only found in Glc/D-Asn, Glc/L-Lys and Fru/D-Lys system, but the content was not increased with increasing pH. 2-acetylfuran (AF) was higher in Glc (or Fru)/L-Lys and Glc (or Fru)/D-Lys systems at pH 7.0. However, at pH 4.0, the content of AF was higher in the Glc (or Fru)/Gly and Glc (or Fru)/L-Asn systems. Therefore, this study aimed to observe the effect of pH, sugars and amino acid enantiomers on the production of furfural and related compounds by the Maillard reaction. A clear tendency was observed for some classes of compounds to be more easily formed at higher or lower pH. HMF was more readily formed at lower pH, while FFA, F, DMHF and MF were inhibited by acidic conditions. Particularly, compounds like FFA, F and MF were not affected by pH changes. In addition, DMHF and MF were only formed in L-Lys and D-Lys system.


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