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Formation of 2,5-dimethyl-4-hydroxy-3(2H)-furanone through methylglyoxal: a Maillard reaction intermediate.

Journal of agricultural and food chemistry (2008-07-03)
Yu Wang, Chi-Tang Ho
RESUMEN

The caramel-like aroma compound, 2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF) was quantified and verified by HPLC and GC-MS in the Maillard reaction based on methylglyoxal (MG). The reaction was performed in the 0.5 M phosphate buffer by heating MG with or without either glycine or cysteine at 120 degrees C for 1 h. MG alone or MG with cysteine could produce increased level of DMHF with pH increased, whereas MG with glycine had contrary trend. Experiments using a 1:1 mixture of [(13)C6]glucose and [(12)C6]glucose indicate that in the presence of glycine or cysteine, glucose skeleton kept intact during DMHF formation since a 1:1 mixture of [(13)C6]DMHF and [(12)C6]DMHF was formed. Acetylformoin was detected in the glucose with amino acid reaction system as a precursor of DMHF, while in the MG reaction systems, acetylformoin could not be identified. It is suggested different pathways of DMHF formation via MG and glucose.

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Sigma-Aldrich
4-Hydroxy-2,5-dimethyl-3(2H)-furanone, ≥98%, FCC, FG
Sigma-Aldrich
4-Hydroxy-2,5-dimethyl-3(2H)-furanone, ≥99.0% (GC)
Sigma-Aldrich
4-Hydroxy-2,5-dimethyl-3(2H)-furanone, natural, ≥98%, FG
Supelco
4-Hydroxy-2,5-dimethyl-3(2H)-furanone, analytical standard