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

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6-Acetyl-2,3,4,5-tetrahydropyridine
Names
Preferred IUPAC name 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-tetrahydropyridine
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1446593, 1446593
ChEBI
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H11NO/c1-6(9)7-4-2-3-5-8-7/h2-5H2,1H3Key: GNZWXNKZMHJXNU-UHFFFAOYSA-N
  • InChI=1/C7H11NO/c1-6(9)7-4-2-3-5-8-7/h2-5H2,1H3Key: GNZWXNKZMHJXNU-UHFFFAOYAY
SMILES
  • O=C(C)C1=NCCCC1
  • O=C(/C1=N/CCCC1)C
Properties
Chemical formula C7H11NO
Molar mass 125.171 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

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:

6-Acetyl-2,3,4,5-tetrahydropyridine ⇌ {\displaystyle \rightleftharpoons } 6-Acetyl-2,3,4,5-tetrahydropyridine
6-Acetyl-2,3,4,5-tetrahydropyridine (1 : 2) 6-Acetyl-1,2,3,4-tetrahydropyridine

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.
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