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{{chembox {{chembox
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| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 443316407 | verifiedrevid = 477215588
|Reference=<ref> at ]</ref> | Reference =<ref> at ]</ref>
|ImageFile=2-Pyranone.png | ImageFile =2-Pyranone.png
|ImageSize=100px | ImageSize =100px
|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 |Section1={{Chembox Identifiers
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| StdInChIKey = ZPSJGADGUYYRKE-UHFFFAOYSA-N | StdInChIKey = ZPSJGADGUYYRKE-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=504-31-4 | CASNo =504-31-4
⚫ | UNII_Ref = {{fdacite|correct|FDA}}
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| UNII = 8WW45I202V
⚫ | ChEBI_Ref = {{ebicite|correct|EBI}}
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| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 37965 | ChEBI = 37965
| SMILES = O=C\1O\C=C/C=C/1 | SMILES = O=C\1O\C=C/C=C/1
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|Section2= {{Chembox Properties |Section2={{Chembox Properties
| C=5|H=4|O=2
| Formula=C<sub>5</sub>H<sub>4</sub>O<sub>2</sub>
| Appearance =
| MolarMass=96.08
⚫ | Density =1.197 g/mL
| Appearance=
| MeltingPt =
⚫ | Density=1.197 g/mL
| BoilingPtC = 102 to 103
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| BoilingPt=102–103&nbsp;°C at 20 mmHg | BoilingPt_notes = at 20 mmHg
| Solubility= | Solubility =
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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 ]. '''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 ].


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}} 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}}


The parent 2-pyrone can be produced from ] of ].<ref>{{cite book|first1=L.&nbsp;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>
<gallery>
Image:4-Pyranone.png|4-Pyrone
</gallery>


==Derivatives==
The most common natural products containing a 2-pyrone are the ] and ]s. 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.


] (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>
⚫ ==References==

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
|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>

==See also==
* ]

⚫ == References ==
<references/> <references/>


{{DEFAULTSORT:Pyrone, 2-}} {{DEFAULTSORT:Pyrone, 2-}}
] ]

]
]
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Latest revision as of 15:46, 5 November 2024

2-Pyrone
Names
Preferred IUPAC name 2H-Pyran-2-one
Other names α-Pyrone
2-Pyranone
Pyran-2-one
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.264 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H4O2/c6-5-3-1-2-4-7-5/h1-4HKey: ZPSJGADGUYYRKE-UHFFFAOYSA-N
  • InChI=1/C5H4O2/c6-5-3-1-2-4-7-5/h1-4HKey: ZPSJGADGUYYRKE-UHFFFAOYAI
SMILES
  • O=C\1O\C=C/C=C/1
Properties
Chemical formula C5H4O2
Molar mass 96.085 g·mol
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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. The Gogte Synthesis (1938) is a method for the alkylation of certain pyrones with acid chlorides.

The parent 2-pyrone can be produced from decarboxylation of coumalic acid.

Derivatives

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. 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.

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.

See also

References

  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. Fieser, L. F.; Fieser, M. (1957). Lehrbuch der organischen Chemie [Textbook of Organic Chemistry] (in German) (3rd ed.). Verlag Chemie. p. 943.
  4. CID 33960 from PubChem
  5. 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.
  6. 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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