2-Acetyl-1-pyrroline

2-Acetyl-1-pyrroline

Other names 2-Acetyl-1-pyrroline
Identifiers
CAS number	85213-22-5^Y
PubChem	522834
ChemSpider	456071^Y
UNII	IGC0W6LY94^Y
MeSH	2-Acetyl-1-pyrroline
Jmol-3D images	Image 1
SMILES CC(=O)C1=NCCC1
InChI InChI=1S/C6H9NO/c1-5(8)6-3-2-4-7-6/h2-4H2,1H3^Y Key: DQBQWWSFRPLIAX-UHFFFAOYSA-N^Y InChI=1/C6H9NO/c1-5(8)6-3-2-4-7-6/h2-4H2,1H3 Key: DQBQWWSFRPLIAX-UHFFFAOYAG
Properties
Molecular formula	C₆H₉NO
Molar mass	111.14 g mol⁻¹
Exact mass	111.068413915 g mol^-1
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 in baked bread. Both compounds have odor thresholds below 0.06 ng/l.^[2]

Structure and properties

2-Acetyl-1-pyrroline is a substituted pyrroline and a cyclic imine as well as a ketone.

^ 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.
^ 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.