Agricultural and Biological Chemistry
Online ISSN : 1881-1280
Print ISSN : 0002-1369
ISSN-L : 0002-1369
Thermal Degradation Products of Several Amadori Compounds
Hitoshi SHIGEMATSUSaizo SHIBATATadao KURATAHiromichi KATOMasao FUJIMAKI
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1977 Volume 41 Issue 12 Pages 2377-2385

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Abstract
Several Amadori compounds, 1-deoxy-l-L-alanino-D-fructose (DAF), 1-deoxy-1-L-valino-D-fructose (DVF), 1-deoxy-l-(N-γ-aminobutyric acid)-D-fructose (DBF) and 1-deoxy-1-L-prolino-D-fructose (DPF), were pyrolyzed at 200°C for 5min and 1.5 hr respectively. Organic solvent extract of 5min pyrolyzate and volatile product obtained by 1.5 hr pyrolysis were examined. Alkyl pyrazines, pyrrole-lactones such as 2-(5'-hydroxymethyl-2'-formylpyrrol-1'-yl) propinoic acid lactone and 2-(5'-hydroxymethyl-2'-formylpyrrol-1'-yl) isovaleric acid lactone, pyrrole-2-aldehydes, 2-acetyl pyrroles, 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4 H-pyran-4-one, 2, 5-dimethyl-4-hydroxy-3 (2 H)-furanone, 1-formyl and 1-acetyl pyrrolidines, 1-acetyl and 1-acetonyl-2-pyrrolidones, 2-pyrrolidone, 1-acyl substituted 2, 3-dihydropyrrolizines and 5, 6, 7, 8-tetrahydroindorizin-8-one were identified. Isolation and identification of these compounds were made by gas chromatographic and spectroscopic methods (MS, IR, NMR and GC-MS). The aromas of degradation products were evaluated by organoleptic test and the degradation pathway of pyrrole-2-aldehydes were postulated by comparison of the composition of 5min pyrolysis products (product A) with those of 1.5 hr pyrolysis (product B).
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