title: Structure determination of a novel 3(6H)-pyranone chromophore and clarification of its formation from carbohydrates and primary amino acids.
abstract: An intensely orange compound, which has recently been evaluated as one of the main colored compounds formed in Maillard reactions of hexoses, could be unequivocally identified as (Z)-2-[(2-furyl)methylidene]-5,6-di(2-furyl)-6H-pyran-3-one (1) by application of several NMR and LC-MS experiments. To clarify its formation, the effectiveness of certain carbohydrate degradation products as precursors of 1 was studied in a quantitative experiment demonstrating hydroxy-2-propanone, furan-2-aldehyde, and 3-deoxy-2-hexosulose as precursors of the colorant. Site-specific labeling experiments with D-1-[(13)C]glucose and D-6-[(13)C]glucose, respectively, were performed to elucidate the formation pathway of 1 involving a cleavage of the hexose skeleton between carbon atoms C(5) and C(6). In addition, pentoses could be shown to generate 1 via a similar formation pathway involving the 3-deoxy-2-pentosulose.
authors: Deutsche Forschungsanstalt für Lebensmittelchemie, Lichtenbergstrasse 4, D-85748 Garching, Germany.
authors: O
authors: O
authors: Frank
authors: S
authors: S
authors: Heuberger
authors: T
authors: T
authors: Hofmann
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D002247:Carbon Isotopes; D005663:Furans / Q000737:chemistry*; D005947:Glucose / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D015394:Molecular Structure; D011714:Pyrans / Q000737:chemistry*; D011753:Pyrones / Q000737:chemistry*
chemical_list: C428985:3(6H)-pyranone chromophore; D000596:Amino Acids; D002241:Carbohydrates; D002247:Carbon Isotopes; D005663:Furans; D011714:Pyrans; D011753:Pyrones; D005947:Glucose