2-Acetyl-1-pyrroline

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2-Acetyl-1-pyrroline
Skeletal formula of 2-acetyl-1-pyrroline
Identifiers
CAS number 85213-22-5 N
PubChem 522834
ChemSpider 456071 YesY
UNII IGC0W6LY94 YesY
MeSH 2-Acetyl-1-pyrroline
ChEBI CHEBI:67125 N
Jmol-3D images Image 1
Properties
Molecular formula C6H9NO
Molar mass 111.14 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

2-Acetyl-1-pyrroline, abbreviated 2AP, with the IUPAC name 1-(3,4-dihydro-2H-pyrrol-5-yl)ethanone, 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 typical smell.[1] 2-Acetyl-1-pyrroline 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.[2]

Structure and properties[edit]

2-Acetyl-1-pyrroline 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. doi:10.1021/jf025856x. PMID 12517110. 
  2. ^ 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.