Detailed investigation of the production of the bread flavor component 6-acetyl-1,2,3,4-tetrahydropyridine in proline 1,3-dihydroxyacetone model systems

被引：16

作者：

Adams, A ^{[1
]}

Tehrani, KA ^{[1
]}

Kersiene, M ^{[1
]}

De Kimpe, N ^{[1
]}

机构：

[1] Univ Ghent, Fac Agr & Appl Biol Sci, Dept Organ Chem, B-9000 Ghent, Belgium

来源：

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY | 2004年 / 52卷 / 18期

关键词：

6-acetyl-1,2,3,4-tetrahydropyridine; bread flavor; 2,3-dihydro-1H-pyrrolizine; model reaction; Maillard flavor;

D O I：

10.1021/jf0496088

中图分类号：

S [农业科学];

学科分类号：

09 ;

摘要：

The production of 6-acetyl-1,2,3,4-tetrahydropyridine (ATHP), an important Maillard flavor component, in the reaction Of L-(-)-proline and 1,3-dihydroxyacetone was investigated as a function of different reaction conditions. The two major side products from the reaction were identified as 5-acetyl-6methyl-2,3-dihydro-1 H-pyrrolizine and 5-acetyl -6- hydroxymethyl -2,3-dihydro-1 H-pyrrolizine, the last one being a new compound described here for the first time. A maximum yield of ATHP of 2.7 mol % from L-(-)-proline and 1,3-dihydroxyacetone was noted at 130 degreesC in the presence of 2 equiv of sodium bisulfite. The role of sodium bisulfite as a reducing species, and as a stabilizing agent for 6-acetyl-1,2,3,4-tetrahydropyridine, was clarified. In view of the new data obtained, the hypothesized mechanism of formation of 6-acetyl-1,2,3,4-tetrahydropyridine was confirmed, and the reaction mechanisms leading to 2,3-dihydro-1 H-pyrrolizines were reconsidered.

引用

页码：5685 / 5693

页数：9

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