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Skeletal formula of 2-acetyl-1-pyrroline
Preferred IUPAC name
Other names
  • 85213-22-5 ☒N
3D model (JSmol)
  • Interactive image
  • CHEBI:67125 ☒N
  • 456071 ☑Y
MeSH 2-Acetyl-1-pyrroline
PubChem CID
  • 522834
  • IGC0W6LY94 ☑Y
Molar mass 111.14 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is ☑Y☒N ?)
Infobox references

2-Acetyl-1-pyrroline (2AP) is an aroma compound and flavor that gives white bread, jasmine rice and basmati rice, the spice pandan (Pandanus amaryllifolius), and bread flowers (Vallaris glabra) their customary smell.[1] 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.[2] Fresh MF (Marking fluid) and urine of the tiger (Indian, Amur or Siberian) and Indian leopard also have a strong aroma due 2AP.[3]

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.[4]

Structure and properties

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


  1. ^ S. Wongpornchai; 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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