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

6-Acetyl-2,3,4,5-tetrahydropyridine, is an aroma compound and

flavor that gives baked goods such as white bread, popcorn, and 6-Acetyl-2,3,4,5-
tortillas their typical smell, together with its structural homolog 2- tetrahydropyridine
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
Names
chemical equilibrium with its tautomer 6-acetyl-1,2,3,4-
tetrahydropyridine that differs only by the position of the double bond Preferred IUPAC name
in the tetrahydropyridine ring: 1-(3,4,5,6-Tetrahydropyridin-2-
yl)ethan-1-one
Other names
1-(3,4,5,6-Tetrahydropyridin-2-
yl)ethanone
2-Acetyl-3,4,5,6-
6-Acetyl-2,3,4,5- 6-Acetyl-1,2,3,4- tetrahydropyridine
(1 : 2)
tetrahydropyridine tetrahydropyridine
Identifiers
CAS Number 27300-27-2 (http://w
References ww.commonchemistr
1. T. J. Harrison, G. R. Dake (2005). "An expeditious, high- y.org/ChemicalDetai
yielding construction of the food aroma compounds 6- l.aspx?ref=27300-27
acetyl-1,2,3,4-tetrahydropyridine and 2-acetyl-1-pyrroline". -2)
J. Org. Chem. 70 (26): 10872–10874.
25343-57-1 (http://w
doi:10.1021/jo051940a (https://doi.org/10.1021%2Fjo0519
40a). PMID 16356012 (https://pubmed.ncbi.nlm.nih.gov/16 ww.commonchemistr
356012). y.org/ChemicalDetai
2. De Kimpe, Norbert; Stevens, Christian (1993). "A l.aspx?ref=25343-57
convenient synthesis of 6-acetyl-1,2,3,4-tetrahydropyridine, -1) tautomer
the principle bread flavor component". Journal of Organic
3D model Interactive image (ht
Chemistry. 58 (10): 2904–2906. doi:10.1021/jo00062a042 (JSmol)
(https://doi.org/10.1021%2Fjo00062a042). tps://chemapps.stola
f.edu/jmol/jmol.php?
model=O%3DC%28
C%29C1%3DNCCC
C1)
Interactive image (ht
tps://chemapps.stola
f.edu/jmol/jmol.php?
 model=O%3DC%2
8%2FC1%3DN%2F
CCCC1%29C)
Beilstein 1446593, 1446593
Reference
ChEBI CHEBI:59533 (http
s://www.ebi.ac.uk/ch
ebi/searchId.do?che
biId=59533)
CHEBI:59534 (http
s://www.ebi.ac.uk/ch
ebi/searchId.do?che
biId=59534)
tautomer
ChemSpider 453844 (http://www.
chemspider.com/Ch
emical-Structure.453
844.html)
PubChem 520194 (https://pubc
CID
hem.ncbi.nlm.nih.go
v/compound/52019
4) tautomer

InChI
InChI=1S/C7H11NO/c1-6(9)7-4-2-3-5-8-7/h2-
5H2,1H3
Key: GNZWXNKZMHJXNU-UHFFFAOYSA-N

InChI=1/C7H11NO/c1-6(9)7-4-2-3-5-8-7/h2-5
H2,1H3
Key: GNZWXNKZMHJXNU-UHFFFAOYAY

SMILES
O=C(C)C1=NCCCC1

O=C(/C1=N/CCCC1)C

Properties
Chemical C7H11NO
formula
Molar mass 125.171 g·mol−1
Except where otherwise noted, data
are given for materials in their
standard state (at 25 °C [77 °F],
100 kPa).
verify (what is ?)
Infobox references

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