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2-Acetyl-1-pyrroline

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2-Acetyl-1-pyrroline
Skeletal formula of 2-acetyl-1-pyrroline
Skeletal formula of 2-acetyl-1-pyrroline
Names
Preferred IUPAC name 1-(3,4-Dihydro-2H-pyrrol-5-yl)ethan-1-one
Other names 1-(3,4-Dihydro-2H-pyrrol-5-yl)ethanone
2-Acetyl-1-pyrroline
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
MeSH 2-Acetyl-1-pyrroline
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H9NO/c1-5(8)6-3-2-4-7-6/h2-4H2,1H3Key: DQBQWWSFRPLIAX-UHFFFAOYSA-N
  • InChI=1/C6H9NO/c1-5(8)6-3-2-4-7-6/h2-4H2,1H3Key: DQBQWWSFRPLIAX-UHFFFAOYAG
SMILES
  • CC(=O)C1=NCCC1
Properties
Chemical formula C6H9NO
Molar mass 111.144 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

2-Acetyl-1-pyrroline (2AP) is an aroma compound and flavor that gives freshly baked bread, jasmine rice and basmati rice, the herb pandan (Pandanus amaryllifolius), and bread flowers (Vallaris glabra) their customary smell. Many observers describe the smell as similar to "hot, buttered popcorn", and it is credited for lending this odor to the scent of binturong (bearcat) urine. Fresh marking fluid (MF) and urine of the tiger (Indian, Amur or Siberian) and Indian leopard also have a strong aroma due to 2AP.

2AP and its structural homolog, 6-acetyl-2,3,4,5-tetrahydropyridine of similar smell, can be formed by Maillard reactions during heating of food such as the baking of bread dough. Both compounds have odor thresholds below 0.06 ng/L.

Structure and properties

2AP is a substituted pyrroline and a cyclic imine as well as a ketone.

References

  1. S. Wongporncha; T. Sriseadka; S. Choonvisase (2003). "Identification and quantitation of the rice aroma compound, 2-acetyl-1-pyrroline, in bread flowers (Vallaris glabra Ktze)". J. Agric. Food Chem. 51 (2): 457–462. doi:10.1021/jf025856x. PMID 12517110.
  2. "Why bearcats smell like buttered popcorn". Duke University/Eurekalert. 2016-04-13.
  3. Brahmachary, Poddar-Sarkar. "Fifty years of tiger pheromone research" (PDF). Archived (PDF) from the original on 2015-06-27. Retrieved 2017-03-25.
  4. 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.
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