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


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. [cite journal
author = T. J. Harrison, G. R. Dake
year = 2005
title = An expeditious, high-yielding construction of the food aroma compounds 6-acetyl-1,2,3,4-tetrahydropyridine and 2-acetyl-1-pyrroline
journal = J. Org. Chem.
volume = 70
issue = 26
pages = 10872–10874
pmid = 16356012
doi = 10.1021/jo051940a
]

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:

See also

* Aroma compound

References


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