# 2-Furanone

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2-Furanone Names Preferred IUPAC name Furan-2(5H)-one Other names Furan-2-one, γ-crotonolactone, butenolide, 5H-furan-2-one Identifiers CAS Number 497-23-4 Y 3D model (JSmol) Interactive image Beilstein Reference 383585 ChEBI CHEBI:38118 Y ChEMBL ChEMBL166223 Y ChemSpider 9917 Y ECHA InfoCard 100.007.128 EC Number 207-839-3 Gmelin Reference 773828 KEGG C17601 Y MeSH butenolide PubChem CID 10341 UNII 8KXK25H388 Y CompTox Dashboard (EPA) DTXSID7075422 InChI InChI=1S/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2 Y Key: VIHAEDVKXSOUAT-UHFFFAOYSA-N Y InChI=1/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2 Key: VIHAEDVKXSOUAT-UHFFFAOYAD SMILES O=C\1OC/C=C/1 Properties Chemical formula 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). Y verify (what is YN ?) Infobox references

Chemical compound

**2-Furanone** is a [heterocyclic](/source/Heterocycle) [organic compound](/source/Organic_compound). It is also known as **γ-crotonolactone** (**GCL**), as it is formally the [lactone](/source/Lactone) derived from γ-hydroxy[isocrotonic acid](/source/Isocrotonic_acid). The chemical is colloquially called "butenolide", and is the parent structure for the [butenolide](/source/Butenolide) class of compounds. It is a colourless liquid.

## Synthesis and reactions

2-Furanone is prepared by oxidation of [furfural](/source/Furfural):[2]

It exists in equilibrium with the [tautomer](/source/Tautomer) 2-hydroxy[furan](/source/Furan), which serves as an intermediate in the interconversion between the β- and α-furanones.[*[further explanation needed](https://en.wikipedia.org/wiki/Wikipedia:Please_clarify)*] The β form is the more stable. The interconversion is catalyzed by [base](/source/Base_(chemistry)).

2-Furanones can be converted to [furans](/source/Furan) by a two-step process of [reduction](/source/Redox_reaction) followed by [dehydration reaction](/source/Dehydration_reaction).

Furanone is thought to contribute to the unique taste of [maple syrup](/source/Maple_syrup).

## See also

- [Category:Furanones](https://en.wikipedia.org/wiki/Category:Furanones), various substituted structural analogs

- [Pyrone](/source/Pyrone), which has one more carbon atom in the ring

## References

1. ^ [***a***](#cite_ref-Sigma_1-0) [***b***](#cite_ref-Sigma_1-1) Sigma-Aldrich Chemicals [Product detail](http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/283754)

1. **[^](#cite_ref-2)** Näsman, Jan H. (1990). "3-Methyl-2(5*H*)-furanone". *Organic Syntheses*. **68**: 162. [doi](/source/Doi_(identifier)):[10.15227/orgsyn.068.0162](https://doi.org/10.15227%2Forgsyn.068.0162).

v t e GHB receptor modulators Receptor (ligands) GHBRTooltip GHB receptor Agonists: Main site: 1,4-BD 3-HPA Aceburic acid (GHB acetate) BDDA (DABD) EAB GBL GCL GHB GHBAL GHV (4-methyl-GHB) GVL HOCHCA HOCPCA JZP-386 MAB NCS-356 NCS-435 Sodium oxybate T-HCA (GHC) THF UMB58 UMB66 UMB68 UMB72 UMB73 UMB86 Valiloxybate (XW-10172); Positive allosteric modulators: (+)-Catechin Monastrol Antagonists: Main site: Gabazine (SR-95531) NCS-382 Unknown/unsorted: Main site: 2-HPA 3-Methyl-GHB 3-Methyl-THCA 4-Benzyl-GHB 4-HPBA 4-Methyl-THCA 4-Phenyl-GHB 4-Phenyl-THCA Amisulpride azido-BnOPh-GHB BnOPh-GHB DHV DVL GTBL Levosulpiride NCS-400 Prochlorperazine Sulpiride Sultopride UMB108 UMB109 UMB119 GABABTooltip γ-Aminobutyric acid B receptor See here instead. Transporter (blockers) MCTsTooltip Monocarboxylate transporters α-Ketoisocaproate Acetoacetic acid AR-C155858 Atorvastatin Benzoic acid BHB Butyric acid CHCA DBDS DIDS Hexanoic acid Lactic acid Luteolin Niflumic acid NPPB Phenylpyruvic acid Phloretin Probenecid Pyruvic acid Quercetin Salicylic acid Simvastatin Sodium valproate Valproic acid SMCTsTooltip Sodium-coupled monocarboxylate transporters Benzoic acid BHB Butyric acid Fenoprofen Ibuprofen Ketoprofen Mesalazine (5-ASA) Naproxen Nicotinic acid Probenecid Propionic acid Pyruvic acid Salicyclic acid VIATTTooltip Vesicular inhibitory amino acid transporter β-Alanine Bafilomycin A1 Butyric acid Evans blue GABA Glycine Nigericin Nipecotic acid Valinomycin Vigabatrin Enzyme (inhibitors) SSRTooltip Succinic semialdehyde reductase Quercetin GHBDHTooltip 4-Hydroxybutyrate dehydrogenase α-Ketoisocaproic acid Ethosuximide Phenylacetate Salicylic acid Valproic acid Enhancers: D-Glucuronic acid HOTTooltip Hydroxyacid-oxoacid transhydrogenase Cyanide Phenanthroline ADHTooltip Alcohol dehydrogenase Cimetidine Ethanol Fomepizole (4-methylpyrazole) Pyrazole ALDHTooltip Aldehyde dehydrogenase Acetaldehyde Cimetidine Cyanamide Disulfiram Prunetin See also Receptor/signaling modulators GABA receptor modulators Glutamate receptor modulators Glycine receptor modulators

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Adapted from the Wikipedia article [2-Furanone](https://en.wikipedia.org/wiki/2-Furanone) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/2-Furanone?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.