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

J Agric Food Chem. 2004 Sep 8;52(18):5685-93. doi: 10.1021/jf0496088.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bread / analysis*
  • Dihydroxyacetone / chemistry*
  • Maillard Reaction
  • Models, Chemical
  • Proline / chemistry*
  • Pyridines / chemical synthesis*
  • Sulfites / chemistry
  • Taste*

Substances

  • 6-acetyl-1,2,3,4-tetrahydropyridine
  • Pyridines
  • Sulfites
  • Proline
  • Dihydroxyacetone
  • sodium bisulfite