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

Journal of Agricultural and Food Chemistry
An AdamsNorbert De Kimpe

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-6-methyl-2,3-dihydro-1H-pyrrolizine and 5-acetyl-6-hydroxymethyl-2,3-dihydro-1H-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 degrees C 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-1H-pyrrolizines were reconsidered.

References

Jul 1, 1979·Journal of Pharmaceutical Sciences·D C Chatterji, J F Gallelli
Oct 25, 2001·The Journal of Organic Chemistry·Edward L. FerroniBeth M. Winkler

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Citations

Sep 21, 2011·Journal of Agricultural and Food Chemistry·An AdamsNorbert De Kimpe
Feb 5, 2013·Journal of Agricultural and Food Chemistry·Candice Smarrito-MenozziFlorian Viton
Mar 6, 2008·Journal of Agricultural and Food Chemistry·An AdamsNorbert De Kimpe

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