2-Acetyl-1-pyrroline

From Wikipedia, the free encyclopedia
Jump to: navigation, search
2-Acetyl-1-pyrroline
Skeletal formula of 2-acetyl-1-pyrroline
Names
Other names
2-Acetyl-1-pyrroline[citation needed]
Identifiers
85213-22-5 N
ChEBI CHEBI:67125 N
ChemSpider 456071 YesY
Jmol 3D model Interactive image
MeSH 2-Acetyl-1-pyrroline
PubChem 522834
UNII IGC0W6LY94 YesY
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).
N verify (what is YesYN ?)
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 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] 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.[3]

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. ^ "Why bearcats smell like buttered popcorn". Duke University/Eurekalert. 2016-04-13. 
  3. ^ 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.