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

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The chemical structure of 6-acetyl-2,3,4,5-tetrahydropyridine

6-Acetyl-2,3,4,5-tetrahydropyridine, with the IUPAC name 1-(3,4,5,6-tetrahydropyridin-2-yl)ethanone, is an aroma compound and flavor that gives baked goods such as white bread, pop corn, or 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]

[edit] Chemistry

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

[edit] See also

Aroma compound

[edit] References

^ 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.