2-Acetyl-1-pyrroline

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477212342

| ImageFile = 2-Acetyl-1-pyrroline.svg

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageName = Skeletal formula of 2-acetyl-1-pyrroline

| PIN = 1-(3,4-Dihydro-2H-pyrrol-5-yl)ethan-1-one

| OtherNames = 1-(3,4-Dihydro-2H-pyrrol-5-yl)ethanone
2-Acetyl-1-pyrroline

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 85213-22-5

| PubChem = 522834

| ChemSpiderID = 456071

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 67125

| MeSHName = 2-Acetyl-1-pyrroline

| UNII = IGC0W6LY94

| UNII_Ref = {{fdacite|correct|FDA}}

| SMILES = CC(=O)C1=NCCC1

| StdInChI = 1S/C6H9NO/c1-5(8)6-3-2-4-7-6/h2-4H2,1H3

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| InChI = 1/C6H9NO/c1-5(8)6-3-2-4-7-6/h2-4H2,1H3

| StdInChIKey=DQBQWWSFRPLIAX-UHFFFAOYSA-N

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| InChIKey = DQBQWWSFRPLIAX-UHFFFAOYAG

}}

|Section2={{Chembox Properties

| C=6 | N=1 | H=9 | O=1

}}

}}

2-Acetyl-1-pyrroline (2AP) 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.{{cite journal

| author1=S. Wongporncha

| author2=T. Sriseadka

| author3=S. Choonvisase

| year = 2003

| title = Identification and quantitation of the rice aroma compound, 2-acetyl-1-pyrroline, in bread flowers (Vallaris glabra Ktze)

| journal = J. Agric. Food Chem.

| volume = 51

| issue = 2

| pages =457–462

| pmid = 12517110

| doi = 10.1021/jf025856x

}} 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.{{cite web|url=http://www.eurekalert.org/pub_releases/2016-04/du-wbs041316.php|title=Why bearcats smell like buttered popcorn|date=2016-04-13|publisher=Duke University/Eurekalert}} Fresh marking fluid (MF) and urine of the tiger (Indian, Amur or Siberian) and Indian leopard also have a strong aroma due to 2AP.{{Cite web|url=http://www.currentscience.ac.in/Volumes/108/12/2178.pdf |title=Fifty years of tiger pheromone research |author1=Brahmachary, Poddar-Sarkar |archiveurl=https://web.archive.org/web/20150627091650/http://www.currentscience.ac.in/Volumes/108/12/2178.pdf |archivedate=2015-06-27 |url-status=live |accessdate=2017-03-25}}

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.{{cite journal

| author1=T. J. Harrison

| author2=G. R. Dake

| year = 2005

| title = An expeditious, high-yielding construction of the food aroma compounds 6-acetyl-1,2,3,4-tetrahydropyridine and 2-acetyl-1-pyrroline

| journal = J. Org. Chem.

| volume = 70

| issue = 26

| pages = 10872–10874

| pmid = 16356012

| doi = 10.1021/jo051940a

}}