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| Names | |||
|---|---|---|---|
| Preferred IUPAC name Furan-2(5H)-one | |||
| Other names Furan-2-one, γ-crotonolactone, butenolide, 5H-furan-2-one | |||
| Identifiers | |||
| |||
3D model (JSmol) | |||
| 383585 | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider |
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| ECHA InfoCard | 100.007.128 | ||
| EC Number |
| ||
| 773828 | |||
| KEGG |
| ||
| MeSH | butenolide | ||
| UNII | |||
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| Properties | |||
| C4H4O2 | |||
| Molar mass | 84.07336 | ||
| Density | 1.185 g/cm3, liquid | ||
| Melting point | 4 to 5 °C (39 to 41 °F; 277 to 278 K)[1] | ||
| Boiling point | 86 to 87 °C (187 to 189 °F; 359 to 360 K) 12 mm Hg[1] | ||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
2-Furanone is aheterocyclicorganic compound. It is also known asγ-crotonolactone (GCL), as it is formally thelactone derived from γ-hydroxyisocrotonic acid. The chemical is colloquially called "butenolide", and is the parent structure for thebutenolide class of compounds. It is a colourless liquid.
2-Furanone is prepared by oxidation offurfural:[2]
It exists in equilibrium with thetautomer 2-hydroxyfuran, which serves as an intermediate in the interconversion between the β- and α-furanones.[further explanation needed] The β form is the more stable. The interconversion is catalyzed bybase.
2-Furanones can be converted tofurans by a two-step process ofreduction followed bydehydration.
Furanone is thought to contribute to the unique taste ofMaple syrup.
