6-Acetyl-2,3,4,5-tetrahydropyridine

6-Acetyl-2,3,4,5-tetrahydropyridine
IUPAC name

1-(3,4,5,6-tetrahydropyridin-2-yl)ethanone
Other names

2-Acetyl-3,4,5,6-tetrahydropyridine
Identifiers
CAS number 25343-57-1 Y
ChemSpider 453844 Y
ChEBI CHEBI:59533 Y
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C7H11NO
Molar mass 125.17 g mol−1
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

6-Acetyl-2,3,4,5-tetrahydropyridine, is an aroma compound and flavor that gives baked goods such as white bread, popcorn, and tortillas their typical smell, together with its structural homolog 2-acetyl-1-pyrroline.

6-Acetyl-2,3,4,5-tetrahydropyridine and 2-acetyl-1-pyrroline are usually formed by Maillard reactions during heating of food. Both compounds have odor thresholds below 0.06 ng/l.[1] [2]

Structure and properties

6-Acetyl-2,3,4,5-tetrahydropyridine is a substituted tetrahydropyridine and a cyclic imine as well as a ketone. The compound exists in a chemical equilibrium with its tautomer 6-acetyl-1,2,3,4-tetrahydropyridine that differs only by the position of the double bond in the tetrahydropyridine ring:

\rightleftharpoons
6-Acetyl-2,3,4,5-tetrahydropyridine (1 : 2) 6-Acetyl-1,2,3,4-tetrahydropyridine

See also

References

  1. ^ T. J. Harrison, G. R. Dake (2005). "An expeditious, high-yielding construction of the food aroma compounds 6-acetyl-1,2,3,4-tetrahydropyridine and 2-acetyl-1-pyrroline". J. Org. Chem. 70 (26): 10872–10874. doi:10.1021/jo051940a. PMID 16356012. 
  2. ^ De Kimpe, Norbert; Stevens, Christian (1993). "A convenient synthesis of 6-acetyl-1,2,3,4-tetrahydropyridine, the principle bread flavor component". Journal of Organic Chemistry 58 (10): 2904–2906. doi:10.1021/jo00062a042.