|
Title
|
|
|
|
Detailed investigation of the production of the bread flavor component 6-acetyl-1,2,3,4-tetrahydropyridine in proline 1,3-dihydroxyacetone model systems
| |
|
Author
|
|
|
|
| |
|
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. |
| |
|
Language
|
|
|
|
English
| |
|
Source (journal)
|
|
|
|
Journal of agricultural and food chemistry. - Washington, D.C.
| |
|
Publication
|
|
|
|
Washington, D.C.
:
2004
| |
|
ISSN
|
|
|
|
0021-8561
| |
|
DOI
|
|
|
|
10.1021/JF0496088
| |
|
Volume/pages
|
|
|
|
52
:18
(2004)
, p. 5685-5693
| |
|
ISI
|
|
|
|
000223666000018
| |
|
Full text (Publisher's DOI)
|
|
|
|
| |
|