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| ImageFile =2-Pyranone.png
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| IUPACName =Pyran-2-one
| PIN =2''H''-Pyran-2-one
| OtherNames =α-Pyrone<br>2-Pyranone<br>2''H''-Pyran-2-one
| OtherNames =α-Pyrone<br>2-Pyranone<br>Pyran-2-one
|Section1={{Chembox Identifiers
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| StdInChIKey = ZPSJGADGUYYRKE-UHFFFAOYSA-N
| StdInChIKey = ZPSJGADGUYYRKE-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|changed|??}}
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo =504-31-4
| CASNo =504-31-4
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 8WW45I202V
| PubChem =68154
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'''2-Pyrone''' ('''α-pyrone''' or '''pyran-2-one''') is an [[saturation (chemistry)|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]].
'''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]].


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}}</ref> The Gogte Synthesis (1938) is a method for the alkylation of certain pyrones with acid chlorides.{{Citation needed|date=March 2008}}
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}}


==Derivatives==
==Derivatives==
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.
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.


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 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| year = 2008| last1 = Ramos| first1 = Aline de Souza| last2 = Fiaux| first2 = Sorele Batista| last3 = Leite| first3 = Selma Gomes Ferreira}}</ref>
[[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>

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
|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>


==See also==
==See also==

Latest revision as of 09:30, 24 January 2024

2-Pyrone[1]
Names
Preferred IUPAC name
2H-Pyran-2-one
Other names
α-Pyrone
2-Pyranone
Pyran-2-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.264 Edit this at Wikidata
UNII
  • InChI=1S/C5H4O2/c6-5-3-1-2-4-7-5/h1-4H checkY
    Key: ZPSJGADGUYYRKE-UHFFFAOYSA-N checkY
  • InChI=1/C5H4O2/c6-5-3-1-2-4-7-5/h1-4H
    Key: ZPSJGADGUYYRKE-UHFFFAOYAI
  • O=C\1O\C=C/C=C/1
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).
☒N verify (what is checkY☒N ?)

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]
  1. ^ 2H-Pyran-2-one at Sigma-Aldrich
  2. ^ 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.
  3. ^ CID 33960 from PubChem
  4. ^ 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.
  5. ^ 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.
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