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| Names | |||
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| Preferred IUPAC name Furan-2(5H)-one | |||
| Other names Furan-2-one, γ-crotonolactone, butenolide, 5H-furan-2-one | |||
| Identifiers | |||
| CAS Number | |||
| 3D model (JSmol) | |||
| Beilstein Reference | 383585 | ||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider | |||
| ECHA InfoCard | 100.007.128 
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| EC Number |
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| Gmelin Reference | 773828 | ||
| KEGG | |||
| MeSH | butenolide | ||
| PubChem CID | |||
| UNII | |||
| CompTox Dashboard (EPA) | |||
InChI
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SMILES
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| Properties | |||
| Chemical formula | C4H4O2 | ||
| Molar mass | 84.07336 | ||
| Density | 1.185 g/cm, liquid | ||
| Melting point | 4 to 5 °C (39 to 41 °F; 277 to 278 K) | ||
| Boiling point | 86 to 87 °C (187 to 189 °F; 359 to 360 K) 12 mm Hg | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
 Y verify (what is ?)
Infobox references
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2-Furanone is a heterocyclic organic compound. It is also known as γ-crotonolactone (GCL), as it is formally the lactone derived from γ-hydroxyisocrotonic acid. The chemical is colloquially called "butenolide", and is the parent structure for the butenolide class of compounds. It is a colourless liquid.
Synthesis and reactions
2-Furanone is prepared by oxidation of furfural:
It exists in equilibrium with the tautomer 2-hydroxyfuran, which serves as an intermediate in the interconversion between the β- and α-furanones. The β form is the more stable. The interconversion is catalyzed by base.
2-Furanones can be converted to furans by a two-step process of reduction followed by dehydration.
Furanone is thought to contribute to the unique taste of Maple syrup.
See also
- Category:Furanones, various substituted structural analogs
- Pyrone, which has one more carbon atom in the ring
References
- ^ Sigma-Aldrich Chemicals Product detail
- Näsman, Jan H. (1990). "3-Methyl-2(5H)-furanone". Organic Syntheses. 68: 162. doi:10.15227/orgsyn.068.0162.
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