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.
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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 | |||
3D model (JSmol) |
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383585 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.007.128 | ||
EC Number |
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773828 | |||
KEGG | |||
MeSH | butenolide | ||
PubChem CID |
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UNII | |||
CompTox Dashboard (EPA) |
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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 their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis and reactions
2-Furanone is prepared by oxidation of furfural:[2]
It exists in equilibrium with the tautomer 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 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
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