Α-pyrone
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IUPAC name
Pyran-2-one
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| Other names
α-Pyrone
2-Pyranone 2H-Pyran-2-one |
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3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.007.264 |
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PubChem CID
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| Properties | |
| C5H4O2 | |
| Molar mass | 96.09 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 |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| Infobox references | |
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. The Gogte Synthesis (1938) is a method for the alkylation of certain pyrones with acid chlorides.
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. Due to its good organoleptic properties with coconut aroma, it is used as flavor enhancer in the food industry. Biologically, it is produced by Trichoderma species via solid state fermentation.
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