Determination of 4-Hydroxy-2,5-dimethyl-3(2H)-furanone and 2(or 5)-Ethyl-4-hydroxy-5(or 2)-methyl-3(2H)-furanone in Pentose Sugar-Based Maillard Model Systems by Isotope Dilution Assays

The formation of 4-hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF) and 2(or 5)-ethyl-4-hydroxy-5(or 2)-methyl-3(2H)-furanone (EHMF) from pentose sugars was studied in Maillard model systems. The amts. generated at 90 DegC for 1 h were detd. by isotope diln. assay (IDA). The internal stds. used for IDA, i.e., [13C2]HDMF and [2H3]EHMF, were prepd. in good overall yields in 3 steps: addn. of labeled acetaldehyde or propionaldehyde to tert-butyloxycarbonyl (BOC)-protected and lithiated 3-butyn-2-ol; oxidn. of the BOC-protected diol with permanganate to 1,2-dione; and finally cyclization to the target mols. after removal of the protective groups under acidic conditions. Quant. data confirmed previous findings that HDMF and EHMF are preferentially formed in the presence of glycine and L-alanine, resp. The yields obtained were 2.6-5.1 mg of HDMF and 6.8-10 mg of EHMF per mmol pentose. Formation of both furanones was favored in phosphate-buffered solns. at pH 7 compared to pH 5, particularly in the presence of an excess of amino acid. These data are well in agreement with the previously proposed formation mechanism of HDMF and EHMF via Strecker-assisted chain elongation of the pentose moiety. However, both furanones were also produced to a lesser extent by sugar fragmentation-condensation reactions. [on SciFinder (R)]


Published in:
Journal of Agricultural and Food Chemistry, 45, 7, 2642-2648
Year:
1997
Keywords:
Note:
CAN 127:64740 17-2 Food and Feed Chemistry Nestle Research Center,Nestec Ltd.,Lausanne,Switz. Journal 0021-8561 written in English. 27538-09-6 (3(2H)-Furanone, 5-ethyl-4-hydroxy-2-methyl-); 27538-10-9 Role: ANT (Analyte), BOC (Biological occurrence), BSU (Biological study, unclassified), MFM (Metabolic formation), ANST (Analytical study), BIOL (Biological study), FORM (Formation, nonpreparative), OCCU (Occurrence) (detn. of 4-hydroxy-2,5-dimethyl-3(2H)-furanone and 2(or 5)-ethyl-4-hydroxy-5(or 2)-methyl-3(2H)-furanone in pentose sugar-based maillard model systems by isotope diln. assays); 3658-77-3 (4-Hydroxy-2,5-dimethyl-3(2H)-furanone) Role: ANT (Analyte), BOC (Biological occurrence), BSU (Biological study, unclassified), MFM (Metabolic formation), PRP (Properties), ANST (Analytical study), BIOL (Biological study), FORM (Formation, nonpreparative), OCCU (Occurrence) (detn. of 4-hydroxy-2,5-dimethyl-3(2H)-furanone and 2(or 5)-ethyl-4-hydroxy-5(or 2)-methyl-3(2H)-furanone in pentose sugar-based maillard model systems by isotope diln. assays); 2028-63-9 (3-Butyn-2-ol); 24424-99-5 (Di-tert-butyl dicarbonate) Role: RCT (Reactant), RACT (Reactant or reagent) (detn. of 4-hydroxy-2,5-dimethyl-3(2H)-furanone and 2(or 5)-ethyl-4-hydroxy-5(or 2)-methyl-3(2H)-furanone in pentose sugar-based maillard model systems by isotope diln. assays); 191528-22-0P; 191528-23-1P; 191528-24-2P; 191528-25-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (detn. of 4-hydroxy-2,5-dimethyl-3(2H)-furanone and 2(or 5)-ethyl-4-hydroxy-5(or 2)-methyl-3(2H)-furanone in pentose sugar-based maillard model systems by isotope diln. assays); 191528-21-9P Role: SPN (Synthetic preparation), PREP (Preparation) (detn. of 4-hydroxy-2,5-dimethyl-3(2H)-furanone and 2(or 5)-ethyl-4-hydroxy-5(or 2)-methyl-3(2H)-furanone in pentose sugar-based maillard model systems by isotope diln. assays)
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 Record created 2006-03-03, last modified 2018-12-03


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