Title
Detailed investigation of the production of the bread flavor component 6-acetyl-1,2,3,4-tetrahydropyridine in proline 1,3-dihydroxyacetone model systemsDetailed investigation of the production of the bread flavor component 6-acetyl-1,2,3,4-tetrahydropyridine in proline 1,3-dihydroxyacetone model systems
Author
Faculty/Department
Faculty of Sciences. Chemistry
Publication type
article
Publication
Washington, D.C.,
Subject
Chemistry
Biology
Pharmacology. Therapy
Source (journal)
Journal of agricultural and food chemistry. - Washington, D.C.
Volume/pages
52(2004):18, p. 5685-5693
ISSN
0021-8561
ISI
000223666000018
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Abstract
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.
E-info
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