| Revision as of 09:06, 6 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:Wi← Previous edit |
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{{chembox |
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{{chembox |
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| verifiedrevid = 443315401 |
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|Reference=<ref> at ]</ref> |
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| verifiedrevid = 477215588 |
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|ImageFile=2-Pyranone.png |
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| Reference =<ref> at ]</ref> |
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|ImageSize=100px |
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| ImageFile =2-Pyranone.png |
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|IUPACName=Pyran-2-one |
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| ImageSize =100px |
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|OtherNames=α-Pyrone<br>2-Pyranone<br>2''H''-Pyran-2-one |
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| PIN =2''H''-Pyran-2-one |
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|Section1= {{Chembox Identifiers |
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| OtherNames =α-Pyrone<br>2-Pyranone<br>Pyran-2-one |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 61462 |
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| ChemSpiderID = 61462 |
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| InChI = 1/C5H4O2/c6-5-3-1-2-4-7-5/h1-4H |
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| InChI = 1/C5H4O2/c6-5-3-1-2-4-7-5/h1-4H |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = ZPSJGADGUYYRKE-UHFFFAOYSA-N |
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| StdInChIKey = ZPSJGADGUYYRKE-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=504-31-4 |
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| CASNo =504-31-4 |
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| PubChem=68154 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 8WW45I202V |
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| PubChem =68154 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 37965 |
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| ChEBI = 37965 |
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| SMILES = O=C\1O\C=C/C=C/1 |
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| SMILES = O=C\1O\C=C/C=C/1 |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=5|H=4|O=2 |
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| Formula=C<sub>5</sub>H<sub>4</sub>O<sub>2</sub> |
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| Appearance = |
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| MolarMass=96.08 |
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| Density =1.197 g/mL |
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| Density=1.197 g/mL |
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| BoilingPtC = 102 to 103 |
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| BoilingPt=102-103 °C at 20 mmHg |
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| BoilingPt_notes = at 20 mmHg |
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|Section3= {{Chembox Hazards |
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'''2-Pyrone''' ('''α-pyrone''' or '''pyran-2-one''') is an ] cyclic chemical compound with the ] formula C<sub>5</sub>H<sub>4</sub>O<sub>2</sub>. It is ]ic with ]. |
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'''2-Pyrone''' ('''α-pyrone''' or '''pyran-2-one''') is an ] cyclic chemical compound with the ] formula C<sub>5</sub>H<sub>4</sub>O<sub>2</sub>. It is ]ic with ]. |
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2-Pyrone is used in ] as a building block for more complex chemical structures because it may participate in a variety of ]s to form bicyclic ]s. For example, it readily undergoes ]s with ]s producing, upon loss of ], substituted ]s.<ref>{{cite journal | author = Woodard BT, ] | title = Recent Advances in Diels-Alder Cycloadditions Using 2-Pyrones | journal = Advances in Cycloaddition | year = 1999 | volume = 5 | pages = 47–83}}</ref> The Gogte Synthesis (1938) is a method for the alkylation of certain pyrones with acid chlorides.{{Citation needed|date=March 2008}} |
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2-Pyrone is used in ] as a building block for more complex chemical structures because it may participate in a variety of ]s to form bicyclic ]s. For example, it readily undergoes ]s with ]s producing, upon loss of ], substituted ]s.<ref>{{cite journal | author = Woodard BT, ] | title = Recent Advances in Diels-Alder Cycloadditions Using 2-Pyrones | journal = Advances in Cycloaddition | year = 1999 | volume = 5 | pages = 47–83| doi = 10.1016/S1052-2077(99)80004-3 }}</ref> The Gogte Synthesis (1938) is a method for the alkylation of certain pyrones with acid chlorides.{{Citation needed|date=March 2008}} |
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The parent 2-pyrone can be produced from ] of ].<ref>{{cite book|first1=L. F.|last1=Fieser|author-link1=Louis Fieser|first2=M.|last2=Fieser|author-link2=Mary Peters Fieser|title=Lehrbuch der organischen Chemie|lang=de|trans-title=Textbook of Organic Chemistry|edition=3rd|publisher=Verlag Chemie|year=1957|page=943}}</ref> |
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<gallery> |
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Image:4-Pyranone.png|4-Pyrone |
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==Derivatives== |
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The most common natural products containing a 2-pyrone are the ] and ]s. |
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The most common natural products containing a 2-pyrone are the ]s and ]s. ], a pyranoanthocyanin found in wine, also contains a 2-pyrone element. |
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] (6PP) is a derivative of 2-pyrone, found in animal foods and heated beef.<ref>{{PubChem|33960}}</ref> Due to its good organoleptic properties{{citation needed|date=July 2020}} with coconut aroma, it is used as flavor enhancer in the food industry. Biologically, it is produced by '']'' species via solid state fermentation.<ref>{{cite journal | doi = 10.1590/S1517-83822008000400022| pmid = 24031295| title = Production of 6-pentyl-α-pyrone by trichoderma harzianum in solid-state fermentation| journal = Brazilian Journal of Microbiology| volume = 39| issue = 4| pages = 712–717| year = 2008| last1 = Ramos| first1 = Aline de Souza| last2 = Fiaux| first2 = Sorele Batista| last3 = Leite| first3 = Selma Gomes Ferreira| pmc=3768464}}</ref> |
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==References== |
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Derivatives of 2-pyrone play a role as signalling molecules in bacterial communication, similar to ]. Cells with LuxR-type receptors, but lacking its homolog LuxI (and thus unable to produce ] QS signaling molecules) are known as LuxR "solos", to which pyrones bind as ligands facilitating cell-cell communication.<ref>{{cite journal |
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|last = Brachmann |first = Alexander |author2=Brameyer, S. |author3=Kresovic, D. |author4=Hitkova, I. |author5=Kopp, Y. |author6=Manske, C. |author7=Schubert, K. |author8=Bode, H. B. |author9=Heermann, R. |title = Pyrones as bacterial signaling molecules |journal=] |volume = 9 |issue = 9 |pages = 573–578 | publisher=] |date=14 July 2013 |doi=10.1038/nchembio.1295 |pmid = 23851573 }}</ref> |
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==See also== |
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* ] |
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== References == |
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{{DEFAULTSORT:Pyrone, 2-}} |
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{{DEFAULTSORT:Pyrone, 2-}} |
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