Formation of Odorants in Maillard Model Systems Based on l-Proline as Affected by pH

Formation of the odorants acetic acid, 4-hydroxy-2,5-dimethyl-3-(2H)-furanone (HDMF), 6-acetyl-1,2,3,4-tetrahydropyridine (ATHP), and 2-acetyl-1-pyrroline (AP) was monitored by isotope dilution assays at pH 6, 7, and 8 in Maillard model reactions containing glucose and proline (Glc/Pro) or the corre...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2003-06, Vol.51 (12), p.3643-3650
Main Authors: Blank, Imre, Devaud, Stéphanie, Matthey-Doret, Walter, Robert, Fabien
Format: Article
Language:English
Subjects:
acetic acid
Biological and medical sciences
Food industries
Fructose - chemistry
Fundamental and applied biological sciences. Psychology
General aspects
glucose
Glucose - chemistry
Hydrogen-Ion Concentration
isotope dilution technique
Kinetics
Maillard Reaction
Miscellaneous
odor compounds
Odorants - analysis
odors
Oxidation-Reduction
Proline - chemistry
Volatilization
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Summary:Formation of the odorants acetic acid, 4-hydroxy-2,5-dimethyl-3-(2H)-furanone (HDMF), 6-acetyl-1,2,3,4-tetrahydropyridine (ATHP), and 2-acetyl-1-pyrroline (AP) was monitored by isotope dilution assays at pH 6, 7, and 8 in Maillard model reactions containing glucose and proline (Glc/Pro) or the corresponding Amadori compound fructosyl-proline (Fru-Pro). In general, higher yields were obtained at pH 7 and 8. Acetic acid was the major odorant with up to 40 mg/mmol precursor followed by HDMF (up to 0.25 mg/mmol), the formation of which was favored in the Fru-Pro reaction systems. On the contrary, ATHP (up to 50 μg/mmol) and AP (up to 5 μg/mmol) were more abundant in Glc/Pro. However, the sensory relevance of the two N-heterocycles was more pronounced on the basis of odor activity values, confirming their contribution to the overall roasty note of the reaction samples. It was also found that formation and decomposition of Fru-Pro were faster at pH 7 as compared to pH 6, explaining in part the preferred formation of the four odorants studied under neutral and slightly alkaline conditions. After 4 h of reaction at pH 7 in the presence of proline, about one-fourth of the glucose was consumed leading to acetic acid with a transformation yield of almost 40 mol %. Keywords: Maillard reaction; l-proline; Amadori compound; N-(1-deoxy-d-fructos-1-yl)-l-proline; isotope dilution assay; GC-MS; odorants; anion exchange chromatography
ISSN:0021-8561
1520-5118
DOI:10.1021/jf034077t