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

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Abstract

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 microg/mmol) and AP (up to 5 microg/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 %.

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