4-Pyrone

4-Pyrone^[1]
Names
	Preferred IUPAC name 4H-Pyran-4-one
	Other names γ-Pyrone; 4-Pyranone
Identifiers
CAS Number	108-97-4 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:37966 ;
ChemSpider	7680 ;
ECHA InfoCard	100.003.305
PubChem CID	7968;
UNII	UJ7X07IM7Z ;
CompTox Dashboard (EPA)	DTXSID20148352 ;
	InChI InChI=1S/C5H4O2/c6-5-1-3-7-4-2-5/h1-4H Key: CVQUWLDCFXOXEN-UHFFFAOYSA-N ; InChI=1/C5H4O2/c6-5-1-3-7-4-2-5/h1-4H Key: CVQUWLDCFXOXEN-UHFFFAOYAG;
	SMILES C1=COC=CC1=O; O=C\1/C=C\O/C=C/1;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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.

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

References

^ 4H-Pyran-4-one at Sigma-Aldrich
^ ^a ^b 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.
^ 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.
^ 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.
^ 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.

[1] 4H-Pyran-4-one at Sigma-Aldrich

[Weygand-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.

[1]

[2]

[3]

[4]

[5]

Preparation

Reactions

Derivatives

See also

References