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.
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| Preferred IUPAC name
2H-Pyran-2-one | |
| Other names
α-Pyrone
2-Pyranone Pyran-2-one | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.007.264 |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C5H4O2 | |
| Molar mass | 96.085 g·mol−1 |
| Density | 1.197 g/mL |
| Boiling point | 102 to 103 °C (216 to 217 °F; 375 to 376 K) at 20 mmHg |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[2] The Gogte Synthesis (1938) is a method for the alkylation of certain pyrones with acid chlorides.[citation needed]
The parent 2-pyrone can be produced from decarboxylation of coumalic acid.[3]
Derivatives
editThe 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.[4] Due to its good organoleptic properties[citation needed] with coconut aroma, it is used as flavor enhancer in the food industry. Biologically, it is produced by Trichoderma species via solid state fermentation.[5]
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.[6]
See also
editReferences
edit- ^ 2H-Pyran-2-one at Sigma-Aldrich
- ^ Woodard BT, Posner G H (1999). "Recent Advances in Diels-Alder Cycloadditions Using 2-Pyrones". Advances in Cycloaddition. 5: 47–83. doi:10.1016/S1052-2077(99)80004-3.
- ^ Fieser, L. F.; Fieser, M. (1957). Lehrbuch der organischen Chemie [Textbook of Organic Chemistry] (in German) (3rd ed.). Verlag Chemie. p. 943.
- ^ CID 33960 from PubChem
- ^ Ramos, Aline de Souza; Fiaux, Sorele Batista; Leite, Selma Gomes Ferreira (2008). "Production of 6-pentyl-α-pyrone by trichoderma harzianum in solid-state fermentation". Brazilian Journal of Microbiology. 39 (4): 712–717. doi:10.1590/S1517-83822008000400022. PMC 3768464. PMID 24031295.
- ^ Brachmann, Alexander; Brameyer, S.; Kresovic, D.; Hitkova, I.; Kopp, Y.; Manske, C.; Schubert, K.; Bode, H. B.; Heermann, R. (14 July 2013). "Pyrones as bacterial signaling molecules". Nature Chemical Biology. 9 (9). Nature Publishing Group: 573–578. doi:10.1038/nchembio.1295. PMID 23851573.