2-Pyrone

changed changed 477215588 2H-Pyran-2-one at Sigma-Aldrich 2-Pyranone.png 100px 2H-Pyran-2-one α-Pyrone2-PyranonePyran-2-one correct chemspider 61462 1/C5H4O2/c6-5-3-1-2-4-7-5/h1-4H ZPSJGADGUYYRKE-UHFFFAOYAI correct chemspider 1S/C5H4O2/c6-5-3-1-2-4-7-5/h1-4H correct chemspider ZPSJGADGUYYRKE-UHFFFAOYSA-N correct CAS 504-31-4 correct FDA 8WW45I202V 68154 correct EBI 37965 O=C\1O\C=C/C=C/1 5 4 2 1.197 g/mL 102 to 103 at 20 mmHg 2-Pyrone (α-pyrone or pyran-2-one) is an unsaturated cyclic chemical compound with the molecular formula C5H4O2. It is isomeric with 4-pyrone. 2-Pyrone is used in organic synthesis as a building block for more complex chemical structures because it may participate in a variety of cycloaddition reactions to form bicyclic lactones. For example, it readily undergoes Diels-Alder reactions with alkynes producing, upon loss of carbon dioxide, substituted benzenes. Woodard BT, Posner G H Recent Advances in Diels-Alder Cycloadditions Using 2-Pyrones Advances in Cycloaddition 1999 5 47–83 10.1016/S1052-2077(99)80004-3 The Gogte Synthesis (1938) is a method for the alkylation of certain pyrones with acid chlorides.March 2008 The parent 2-pyrone can be produced from decarboxylation of coumalic acid.L. F. Fieser Louis Fieser M. Fieser Mary Peters Fieser Lehrbuch der organischen Chemie de Textbook of Organic Chemistry 3rd Verlag Chemie 1957 943 Derivatives The most common natural products containing a 2-pyrone are the bufanolides and kavalactones. Oxovitisin A, a pyranoanthocyanin found in wine, also contains a 2-pyrone element. 6-Amyl-α-pyrone (6PP) is a derivative of 2-pyrone, found in animal foods and heated beef.33960 Due to its good organoleptic propertiesJuly 2020 with coconut aroma, it is used as flavor enhancer in the food industry. Biologically, it is produced by Trichoderma species via solid state fermentation. 10.1590/S1517-83822008000400022 24031295 Production of 6-pentyl-α-pyrone by trichoderma harzianum in solid-state fermentation Brazilian Journal of Microbiology 39 4 712–717 2008 Ramos Aline de Souza Fiaux Sorele Batista Leite Selma Gomes Ferreira 3768464 Derivatives of 2-pyrone play a role as signalling molecules in bacterial communication, similar to quorum sensing. Cells with LuxR-type receptors, but lacking its homolog LuxI (and thus unable to produce N-acylhomoserine lactone QS signaling molecules) are known as LuxR "solos", to which pyrones bind as ligands facilitating cell-cell communication. Brachmann Alexander Brameyer, S. Kresovic, D. Hitkova, I. Kopp, Y. Manske, C. Schubert, K. Bode, H. B. Heermann, R. Pyrones as bacterial signaling molecules Nature Chemical Biology 9 9 573–578 Nature Publishing Group 14 July 2013 10.1038/nchembio.1295 23851573 See also Pyrone References