title: Formation of the reduced form of furaneol® (2,5-dimethyl-4-hydroxy-tetrahydrofuran-3-one) during the Maillard reaction through catalysis of amino acid metal salts.
abstract: Under pyrolytic conditions the acidity/basicity of Maillard reaction mixtures can be controlled through the use of hydrochloride or sodium salts of amino acids to generate a diversity of products. When the degradation of glucose was studied under pyrolytic conditions using excess sodium glycinate the reaction was found to generate a major unknown peak having a molecular ion at m/z 130. Subsequent in-depth isotope labelling studies indicated that acetol was an important precursor of this compound under pyrolytic and aqueous heating conditions. The dimerisation and cyclisation of acetol into 2,5-dimethyl-4-hydroxy-tetrahydrofuran-3-one was found to be catalysed by amino acid metal salts. Also, ESI/qTOF/MS studies indicated that the unknown peak has expected molecular formula of C6H10O3. Finally, a peak having the same retention time and mass spectrum was also generated pyrolytically when furaneol® was reduced with NaBH4 confirming the initial hypothesis regarding the unknown peak to be the reduced form of furaneol®.
authors.affiliation: Department of Food Science and Agricultural Chemistry, McGill University, 21,111 Lakeshore, Ste. Anne de Bellevue, Quebec H9X 3V9, Canada.
authors.forename: Ossanna
authors.initials: O
authors.lastname: Nashalian
authors.affiliation: Department of Food Science and Agricultural Chemistry, McGill University, 21,111 Lakeshore, Ste. Anne de Bellevue, Quebec H9X 3V9, Canada.
authors.forename: Xi
authors.initials: X
authors.lastname: Wang
authors.affiliation: Department of Food Science and Agricultural Chemistry, McGill University, 21,111 Lakeshore, Ste. Anne de Bellevue, Quebec H9X 3V9, Canada. Electronic address: varoujan.yaylayan@mcgill.ca.
authors.forename: Varoujan A
authors.initials: VA
authors.lastname: Yaylayan
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis*; D005947:Glucose / Q000737:chemistry*; D015416:Maillard Reaction; D008670:Metals
chemical_list: D000596:Amino Acids; D005663:Furans; D008670:Metals; C058427:furaneol; C018674:tetrahydrofuran; D005947:Glucose
keywords: Acetol; Aldol reaction; Amino acid metal salts; Furaneol®; Glucose; Lactaldehdye; Maillard reaction