2-Pyrone

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[1]
Names
IUPAC name
Pyran-2-one
Other names
α-Pyrone
2-Pyranone
2H-Pyran-2-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.264
UNII
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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Infobox references

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.

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.[3] 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.[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]

gollark: It's not a websocket "sender".
gollark: You would just need one file which either just checks if it's on CC or the server and acts accordingly, or do some wizardry to make it valid code in multiple languages.
gollark: True, true.
gollark: A server and a client.
gollark: Two, actually.

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.
  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. 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. Nature Publishing Group. 9 (9): 573–578. doi:10.1038/nchembio.1295. PMID 23851573.
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