2-Acetyl-1-pyrroline

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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
3D model (JSmol)
ChEBI
ChemSpider
MeSH 2-Acetyl-1-pyrroline
UNII
Properties
C6H9NO
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).
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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[edit]

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

References[edit]

  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. PMID 12517110. doi:10.1021/jf025856x. 
  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. PMID 16356012. doi:10.1021/jo051940a.