title: Formation of 2,5-dimethyl-4-hydroxy-3(2H)-furanone through methylglyoxal: a Maillard reaction intermediate.
abstract: 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.
authors.affiliation: Department of Food Science, Rutgers University, New Brunswick, New Jersey 08901-8520, USA.
authors.forename: Yu
authors.initials: Y
authors.lastname: Wang
authors.forename: Chi-Tang
authors.initials: CT
authors.lastname: Ho
mesh_terms: D002851:Chromatography, High Pressure Liquid; D005663:Furans / Q000138:chemical synthesis*; D008401:Gas Chromatography-Mass Spectrometry; D005947:Glucose / Q000737:chemistry; D015416:Maillard Reaction; D009812:Odorants / Q000032:analysis; D011765:Pyruvaldehyde / Q000737:chemistry*
chemical_list: D005663:Furans; C058427:furaneol; D011765:Pyruvaldehyde; D005947:Glucose