2-Acetyl-1-pyrroline

changed changed 477212342 2-Acetyl-1-pyrroline.svg correct ?? Skeletal formula of 2-acetyl-1-pyrroline 1-(3,4-Dihydro-2H-pyrrol-5-yl)ethan-1-one 1-(3,4-Dihydro-2H-pyrrol-5-yl)ethanone2-Acetyl-1-pyrroline correct CAS 85213-22-5 522834 456071 correct chemspider changed EBI 67125 2-Acetyl-1-pyrroline IGC0W6LY94 correct FDA CC(=O)C1=NCCC1 1S/C6H9NO/c1-5(8)6-3-2-4-7-6/h2-4H2,1H3 correct chemspider 1/C6H9NO/c1-5(8)6-3-2-4-7-6/h2-4H2,1H3 DQBQWWSFRPLIAX-UHFFFAOYSA-N correct chemspider DQBQWWSFRPLIAX-UHFFFAOYAG 6 1 9 1 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.Wakte Kantilal Zanan Rahul Hinge Vidya Khandagale Kiran Nadaf Altafhusain Henry Robert 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 2017 97 2 384–395 10.1002/jsfa.7875 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 12517110 10.1021/jf025856x 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.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 16356012 10.1021/jo051940a Other It has also been credited for lending this odor to the scent of binturong (bearcat) urine.http://www.eurekalert.org/pub_releases/2016-04/du-wbs041316.php Why bearcats smell like buttered popcorn 2016-04-13 Duke University/Eurekalert 2016-04-14 2021-01-20 https://web.archive.org/web/20210120043136/https://www.eurekalert.org/pub_releases/2016-04/du-wbs041316.php dead Fresh marking fluid (MF) and urine of the tiger (Indian, Amur or Siberian) and Indian leopard also have a strong aroma due to 2AP.http://www.currentscience.ac.in/Volumes/108/12/2178.pdf Fifty years of tiger pheromone research Brahmachary, Poddar-Sarkar https://web.archive.org/web/20150627091650/http://www.currentscience.ac.in/Volumes/108/12/2178.pdf 2015-06-27 live 2017-03-25 Structure and properties 2AP is a substituted pyrroline and a cyclic imine as well as a ketone. References Category:Flavors Category:Acetyl compounds Category:Imines Category:Pyrrolines