Formation of 4-Hydroxy-2,5-dimethyl-3(2H)-furanone and 4-Hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone through Maillard Reaction Based on Pentose Sugars

• Published in: Journal of agricultural and food chemistry Vol. 44; no. 2; pp. 531 - 536
• Main Authors: Blank, Imre, Fay, Laurent B
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 1996; Amer Chemical Soc
• Subjects: Agriculture; Agriculture, Multidisciplinary; ALANINA; ALANINE; AMADORI COMPOUNDS; AZUCARES; Biological and medical sciences; Chemistry; Chemistry, Applied; Food industries; Food Science & Technology; Fundamental and applied biological sciences. Psychology; FURANE; FURANOS; FURANS; General aspects; GLICINA; GLYCINE (ACIDE AMINE); GLYCINE (AMINO ACID); Life Sciences & Biomedicine; MAILLARD REACTION; Methods of analysis, processing and quality control, regulation, standards; MODELE; MODELOS; MONOSACARIDOS; MONOSACCHARIDE; MONOSACCHARIDES; PENTOSE MODEL SYSTEM; Physical Sciences; REACCION DE MAILLARD; REACTION DE MAILLARD; Science & Technology; SUCRES; SUGARS; POTENT ODORANTS; 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone; EXTRACT DILUTION ANALYSIS; Maillard reaction; FLAVOR COMPONENT; AROMA; GC-MSIMS; FOODS; FURANEOL; BEEF; 4-hydroxy-2,5-dimethyl-3(2H)-furanone; pentose model system; Gas chromatography; Alanine; Radiolabelling; Pentose; Furan derivatives; Reaction mechanism; Strecker synthesis; Identification; Glycine
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf950439o

The caramel-like smelling compounds 4-hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF) and 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone (HEMF) were identified by GC−MS and GC−MS/MS in Maillard reaction systems based on pentoses. The reaction was performed in a phosphate buffer by heating xylose, ribose, or arabinose with glycine or l-alanine at 90 °C for 1 h. HEMF was detected in the system pentose/alanine. HDMF was formed in both pentose/glycine and pentose/alanine systems as well as directly from pentoses. Experiments using 13C-labeled glycine and alanine suggest the incorporation of the Strecker degradation products formaldehyde and acetaldehyde into the pentose moiety, forming the furanones HDMF and HEMF, respectively. The presence of 12C-HDMF, which was approximately 30% of the total HDMF amount found in xylose/glycine, indicates that HDMF is partly formed by sugar fragmentation. The proposed mechanism for the formation of the furanones is based on decomposition of the Amadori compound via 2,3-enolization, chain elongation by the Strecker aldehydes, and reduction of the resulting acetylformoin-type intermediates to the target molecules. Keywords: Maillard reaction; pentose model system; 4-hydroxy-2,5-dimethyl-3(2H)-furanone; 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone; GC−MS/MS