| Revision as of 17:19, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 446890457 of page 2-Furanone for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 14:34, 24 November 2024 edit Bearian (talk | contribs)Autopatrolled, Extended confirmed users, New page reviewers, Rollbackers84,814 edits →Synthesis and reactions: Furanone is thought to contribute to the unique taste of Maple syrup.Tags: Mobile edit Mobile web edit |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 443314203 |
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| verifiedrevid = 477213431 |
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| ImageFile = Furan-2-one.png |
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| ImageFileL1 = Furan-2-one.svg |
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| ImageSize = 150px |
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| ImageSizeL1 = 120 |
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| IUPACName = 5H-furan-2-one |
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| ImageAltL1 = Skeletal formula of 2-furanone |
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| OtherNames = furan-2-one, γ-crotonolactone, β-angelica lactone, butenolide |
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| ImageFileR1 = 2-Furanone-3D-balls.png |
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| ImageSizeR1 = 130 |
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| ImageAltR1 = Ball-and-stick model of the 2-furanone molecule |
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| PIN = Furan-2(5''H'')-one |
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| OtherNames = Furan-2-one, γ-crotonolactone, butenolide, 5''H''-furan-2-one |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| Beilstein = 383585 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| Gmelin = 773828 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C17601 |
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| KEGG = C17601 |
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| InChI = 1/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2 |
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| InChI = 1/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 166223 |
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| ChEMBL = 166223 |
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| EC_number = 207-839-3 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2 |
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| StdInChI = 1S/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 497-23-4 |
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| CASNo = 497-23-4 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem = 10341 |
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| UNII = 8KXK25H388 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| PubChem = 10341 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 38118 |
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| ChEBI = 38118 |
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| SMILES = O=C\1OC/C=C/1 |
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| SMILES = O=C\1OC/C=C/1 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 9917 |
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| ChemSpiderID = 9917 |
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| MeSHName = butenolide |
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| MeSHName = butenolide |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| Formula = C<sub>4</sub>H<sub>4</sub>O<sub>2</sub> |
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| Formula = C<sub>4</sub>H<sub>4</sub>O<sub>2</sub> |
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| MolarMass = 84.07336 |
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| MolarMass = 84.07336 |
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| Appearance = |
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| Appearance = |
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| Density = 1.185 g/cm<sup>3</sup>, liquid |
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| Density = 1.185 g/cm<sup>3</sup>, liquid |
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| MeltingPtCL = 4 |
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| MeltingPtC = 4 to 5 |
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| MeltingPt_ref=<ref name="Sigma">Sigma-Aldrich Chemicals </ref> |
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| MeltingPtCH = 5 |
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| BoilingPtC = 86 to 87 |
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| Melting_notes=Source<ref name="Sigma">Sigma-Aldrich Chemicals </ref> |
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| BoilingPt_notes= 12 mm Hg<ref name="Sigma"/> |
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| BoilingPtCL = 86 |
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| Solubility = |
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| BoilingPtCH = 87 |
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| Boiling_notes= 12 mm Hg, Source<ref name="Sigma"/> |
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| Solubility = |
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| Section7 = {{Chembox Hazards |
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| Section7 = {{Chembox Hazards |
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| MainHazards = |
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| Autoignition = |
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'''2-Furanone''' is a ] ]. It is also known as '''γ-crotonolactone''' ('''GCL'''), as it is formally the ] derived from γ-hydroxy]. The chemical is colloquially called "butenolide", and is the parent structure for the ] class of compounds. It is a colourless liquid. |
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==Synthesis and reactions== |
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2-Furanone is prepared by oxidation of ]:<ref>{{cite journal|last1=Näsman|first1=Jan H.|title=3-Methyl-2(5''H'')-furanone|journal=Organic Syntheses|date=1990|volume=68|page=162|doi=10.15227/orgsyn.068.0162}}</ref> |
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:] |
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It exists in equilibrium with the ] 2-hydroxy], which serves as an intermediate in the interconversion between the β- and α-furanones.{{explain|reason=What are the alpha and beta forms?|date=October 2017}} The β form is the more stable. The interconversion is catalyzed by ]. |
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2-Furanones can be converted to ]s by a two-step process of ] followed by ]. |
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Furanone is thought to contribute to the unique taste of ]. |
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==See also== |
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* ], various substituted structural analogs |
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* ], which has one more carbon atom in the ring |
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==References== |
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{{Reflist}} |
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{{GHBergics}} |
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{{DEFAULTSORT:Furanone, 2-}} |
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] |
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] |