2-Acetyl-1-pyrroline

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
CAS Number	85213-22-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:67125 ;
ChemSpider	456071 ;
MeSH	2-Acetyl-1-pyrroline
PubChem CID	522834;
UNII	IGC0W6LY94 ;
CompTox Dashboard (EPA)	DTXSID40335080 ;
	InChI InChI=1S/C6H9NO/c1-5(8)6-3-2-4-7-6/h2-4H2,1H3 Key: DQBQWWSFRPLIAX-UHFFFAOYSA-N ; InChI=1/C6H9NO/c1-5(8)6-3-2-4-7-6/h2-4H2,1H3 Key: DQBQWWSFRPLIAX-UHFFFAOYAG;
	SMILES CC(=O)C1=NCCC1;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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]

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

^ Wakte, Kantilal; Zanan, Rahul; Hinge, Vidya; Khandagale, Kiran; Nadaf, Altafhusain; Henry, Robert (2017). "Thirty-three years of 2-acetyl-1-pyrroline, a principal basmati aroma compound in scented rice ( Oryza sativa L.): A status review". Journal of the Science of Food and Agriculture. 97 (2): 384–395. doi:10.1002/jsfa.7875. PMID 27376959.
^ S. Wongporncha; 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.
^ "Why bearcats smell like buttered popcorn". Duke University/Eurekalert. 2016-04-13.
^ Brahmachary, Poddar-Sarkar. "Fifty years of tiger pheromone research" (PDF). Archived (PDF) from the original on 2015-06-27. Retrieved 2017-03-25.

[1] Wakte, Kantilal; Zanan, Rahul; Hinge, Vidya; Khandagale, Kiran; Nadaf, Altafhusain; Henry, Robert (2017). "Thirty-three years of 2-acetyl-1-pyrroline, a principal basmati aroma compound in scented rice ( Oryza sativa L.): A status review". Journal of the Science of Food and Agriculture. 97 (2): 384–395. doi:10.1002/jsfa.7875. PMID 27376959.

[wongpornchai-2] S. Wongporncha; 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.

[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.

[4] "Why bearcats smell like buttered popcorn". Duke University/Eurekalert. 2016-04-13.

[5] Brahmachary, Poddar-Sarkar. "Fifty years of tiger pheromone research" (PDF). Archived (PDF) from the original on 2015-06-27. Retrieved 2017-03-25.

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