4-Pyrone

4-Pyrone (γ-pyrone or pyran-4-one) is an unsaturated cyclic chemical compound with the molecular formula C5H4O2. It is isomeric with 2-pyrone.

4-Pyrone[1]
Names
Preferred IUPAC name
4H-Pyran-4-one
Other names
γ-Pyrone
4-Pyranone
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.305
UNII
  • InChI=1S/C5H4O2/c6-5-1-3-7-4-2-5/h1-4H checkY
    Key: CVQUWLDCFXOXEN-UHFFFAOYSA-N checkY
  • InChI=1/C5H4O2/c6-5-1-3-7-4-2-5/h1-4H
    Key: CVQUWLDCFXOXEN-UHFFFAOYAG
  • C1=COC=CC1=O
  • O=C\1/C=C\O/C=C/1
Properties
C5H4O2
Molar mass 96.08
Melting point 32 to 34 °C (90 to 93 °F; 305 to 307 K)
Boiling point 210 to 215 °C (410 to 419 °F; 483 to 488 K)
Hazards
Flash point 101 °C (214 °F; 374 K)
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

Preparation

4-Pyrone is prepared via the thermal decarboxylation of chelidonic acid.[2]

Reactions

4-Pyrone and its derivatives react with amines in protic solvents to form 4-Pyridones.[2][3][4]

Derivatives

4-Pyrone forms the central core of several natural chemical compounds,[5] including maltol, meconic acid, kojic acid, and of the important class of the Flavones.

Maltol Kojic acid

See also

References
  1. 4H-Pyran-4-one at Sigma-Aldrich
  2. Weygand, Conrad (1972). Hilgetag, G.; Martini, A. (eds.). Weygand/Hilgetag Preparative Organic Chemistry (4th ed.). New York: John Wiley & Sons, Inc. pp. 533–534, & 1009. ISBN 0471937495.
  3. Van Allan, J. A.; Reynolds, G. A.; Alessi, J. T.; Chie Chang, S.; C. Joines, R. (1971). "Reactions of 4‐pyrones with primary amines. A new class of ionic associates". Journal of Heterocyclic Chemistry. 8 (6): 919–922. doi:10.1002/jhet.5570080606.
  4. Cook, Denys (1963). "The Preparation, Properties, and Structure of 2,6-bis-(Alkyamino)-2,5-heptadien-4-ones". Canadian Journal of Chemistry. 41 (6): 1435–1440. doi:10.1139/v63-195.
  5. Wilk, Wolfram; Waldmann, Herbert; Kaiser, Markus (2009). "Γ-Pyrone natural products—A privileged compound class provided by nature". Bioorganic & Medicinal Chemistry. 17 (6): 2304–2309. doi:10.1016/j.bmc.2008.11.001. PMID 19042133.
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