2-Pyrone: Difference between revisions
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| ImageFile =2-Pyranone.png |
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| OtherNames =α-Pyrone<br>2-Pyranone<br>Pyran-2-one |
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| PubChem=68154 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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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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| Formula=C<sub>5</sub>H<sub>4</sub>O<sub>2</sub> |
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| InChIKey = ZPSJGADGUYYRKE-UHFFFAOYAI |
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| MolarMass=96.08 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| Appearance= |
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| StdInChI = 1S/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 = ZPSJGADGUYYRKE-UHFFFAOYSA-N |
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| BoilingPt=102-103 °C at 20 mmHg |
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| UNII = 8WW45I202V |
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| PubChem =68154 |
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| ChEBI = 37965 |
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| C=5|H=4|O=2 |
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| BoilingPtC = 102 to 103 |
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'''2-Pyrone''' ('''α-pyrone''' or '''pyran-2-one''') is an [[unsaturated]] cyclic chemical compound with the [[molecule|molecular]] formula C<sub>5</sub>H<sub>4</sub>O<sub>2</sub>. |
'''2-Pyrone''' ('''α-pyrone''' or '''pyran-2-one''') is an [[Saturated and unsaturated compounds|unsaturated]] cyclic chemical compound with the [[molecule|molecular]] formula C<sub>5</sub>H<sub>4</sub>O<sub>2</sub>. It is [[isomer]]ic with [[4-pyrone]]. |
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⚫ | 2-Pyrone is used in [[organic synthesis]] as a building block for more complex chemical structures because it may participate in a variety of [[cycloaddition reaction]]s to form bicyclic [[lactone]]s. For example, it readily undergoes [[Diels-Alder reaction]]s with [[alkyne]]s producing, upon loss of [[carbon dioxide]], substituted [[benzene]]s.<ref>{{cite journal | author = Woodard BT, [[Gary H. Posner|Posner G H]] | 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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==Derivatives== |
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The most common natural products containing a 2-pyrone are the [[bufanolide]]s and [[kavalactone]]s. [[Oxovitisin A]], a pyranoanthocyanin found in wine, also contains a 2-pyrone element. |
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[[6-Amyl-α-pyrone]] (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 ''[[Trichoderma]]'' 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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⚫ | 2-Pyrone is used in [[organic synthesis]] as a building block for more complex chemical structures because it may participate in a variety of [[cycloaddition reaction]]s to form bicyclic [[lactone]]s. For example, it readily undergoes [[Diels-Alder reaction]]s with [[alkyne]]s producing, upon loss of [[carbon dioxide]], substituted [[benzene]]s.<ref>Woodard BT, Posner G H |
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Derivatives of 2-pyrone play a role as signalling molecules in bacterial communication, similar to [[quorum sensing]]. Cells with LuxR-type receptors, but lacking its homolog LuxI (and thus unable to produce [[N-Acyl Homoserine Lactone|''N''-acylhomoserine lactone]] 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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2-Pyrone also forms the core structure of a variety of natural organic compounds. For example, the [[coumarin]]s are an important class of compounds which are benzo-fused derivatives of 2-pyrone. |
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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=[[Nature Chemical Biology]] |volume = 9 |issue = 9 |pages = 573–578 | publisher=[[Nature Publishing Group]] |date=14 July 2013 |doi=10.1038/nchembio.1295 |pmid = 23851573 }}</ref> |
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==See also== |
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<gallery> |
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* [[Pyrone]] |
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Image:4-Pyranone.png|4-Pyrone |
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Image:Coumarin acsv.svg|Coumarin |
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</gallery> |
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==References== |
== References == |
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<references/> |
<references/> |
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{{DEFAULTSORT:Pyrone, 2-}} |
{{DEFAULTSORT:Pyrone, 2-}} |
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[[Category: |
[[Category:2-Pyrones| ]] |
Latest revision as of 09:30, 24 January 2024
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Names | |
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Preferred IUPAC name
2H-Pyran-2-one | |
Other names
α-Pyrone
2-Pyranone Pyran-2-one | |
Identifiers | |
3D model (JSmol)
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ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.007.264 |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C5H4O2 | |
Molar mass | 96.085 g·mol−1 |
Density | 1.197 g/mL |
Boiling point | 102 to 103 °C (216 to 217 °F; 375 to 376 K) at 20 mmHg |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2-Pyrone (α-pyrone or pyran-2-one) is an unsaturated cyclic chemical compound with the molecular formula C5H4O2. It is isomeric with 4-pyrone.
2-Pyrone is used in organic synthesis as a building block for more complex chemical structures because it may participate in a variety of cycloaddition reactions to form bicyclic lactones. For example, it readily undergoes Diels-Alder reactions with alkynes producing, upon loss of carbon dioxide, substituted benzenes.[2] The Gogte Synthesis (1938) is a method for the alkylation of certain pyrones with acid chlorides.[citation needed]
Derivatives
[edit]The most common natural products containing a 2-pyrone are the bufanolides and kavalactones. Oxovitisin A, a pyranoanthocyanin found in wine, also contains a 2-pyrone element.
6-Amyl-α-pyrone (6PP) is a derivative of 2-pyrone, found in animal foods and heated beef.[3] Due to its good organoleptic properties[citation needed] with coconut aroma, it is used as flavor enhancer in the food industry. Biologically, it is produced by Trichoderma species via solid state fermentation.[4]
Derivatives of 2-pyrone play a role as signalling molecules in bacterial communication, similar to quorum sensing. Cells with LuxR-type receptors, but lacking its homolog LuxI (and thus unable to produce N-acylhomoserine lactone QS signaling molecules) are known as LuxR "solos", to which pyrones bind as ligands facilitating cell-cell communication.[5]
See also
[edit]References
[edit]- ^ 2H-Pyran-2-one at Sigma-Aldrich
- ^ Woodard BT, Posner G H (1999). "Recent Advances in Diels-Alder Cycloadditions Using 2-Pyrones". Advances in Cycloaddition. 5: 47–83. doi:10.1016/S1052-2077(99)80004-3.
- ^ CID 33960 from PubChem
- ^ Ramos, Aline de Souza; Fiaux, Sorele Batista; Leite, Selma Gomes Ferreira (2008). "Production of 6-pentyl-α-pyrone by trichoderma harzianum in solid-state fermentation". Brazilian Journal of Microbiology. 39 (4): 712–717. doi:10.1590/S1517-83822008000400022. PMC 3768464. PMID 24031295.
- ^ Brachmann, Alexander; Brameyer, S.; Kresovic, D.; Hitkova, I.; Kopp, Y.; Manske, C.; Schubert, K.; Bode, H. B.; Heermann, R. (14 July 2013). "Pyrones as bacterial signaling molecules". Nature Chemical Biology. 9 (9). Nature Publishing Group: 573–578. doi:10.1038/nchembio.1295. PMID 23851573.