2-Acetyl-1-pyrroline

Chemical compound From Wikipedia, the free encyclopedia

2-Acetyl-1-pyrroline (2AP) is an organic compound with the formula CH3C(O)C4H6N. In terms of structure, it is a derivative of 1-pyrroline. It 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.[1][2] Many observers describe the smell as similar to "hot, buttered popcorn" 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.[3]

Quick facts Names, Identifiers ...
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
3D model (JSmol)
ChEBI
ChemSpider
MeSH 2-Acetyl-1-pyrroline
UNII
  • InChI=1S/C6H9NO/c1-5(8)6-3-2-4-7-6/h2-4H2,1H3 checkY
    Key: DQBQWWSFRPLIAX-UHFFFAOYSA-N checkY
  • InChI=1/C6H9NO/c1-5(8)6-3-2-4-7-6/h2-4H2,1H3
    Key: DQBQWWSFRPLIAX-UHFFFAOYAG
  • CC(=O)C1=NCCC1
Properties
C6H9NO
Molar mass 111.144 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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Other

It has also been credited for lending this odor to the scent of binturong (bearcat) urine.[4] Fresh marking fluid (MF) and urine of the tiger (Indian, Amur or Siberian) and Indian leopard also have a strong aroma due to 2AP.[5]

Structure and properties

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

References

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