Coumalic acid

Coumalic acid
Names
	Preferred IUPAC name 2-Oxo-2H-pyran-5-carboxylic acid
	Other names Cumalic acid
Identifiers
CAS Number	500-05-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:180952;
ChEMBL	ChEMBL216734;
ChemSpider	61449;
ECHA InfoCard	100.007.182
EC Number	207-899-0;
PubChem CID	68141;
UNII	OB1JPY343G;
CompTox Dashboard (EPA)	DTXSID60870569 ;
	InChI InChI=1S/C6H4O4/c7-5-2-1-4(3-10-5)6(8)9/h1-3H,(H,8,9) Key: ORGPJDKNYMVLFL-UHFFFAOYSA-N;
	SMILES C1=CC(=O)OC=C1C(=O)O;
Properties
Chemical formula	C6H4O4
Molar mass	140.094 g·mol−1
Appearance	yellow solid
Melting point	210 °C (410 °F; 483 K)
Hazards
	GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Coumalic acid is an organic compound with the molecular formula C₆H₄O₄. Its melting point is around 210 °C.^[1]

In laboratory coumalic acid may be obtained by self-condensation of malic acid in fuming sulfuric acid:^[2]

References

^ Wiley, Richard H.; Knabeschuh, Louis H. (1955). "'2-Pyrones. XIII. The Chemistry of Coumalic Acid and its Derivatives". Journal of the American Chemical Society. 77: 1615. doi:10.1021/ja01611a062.
^ Richard H. Wiley and Newton R. Smith (1951). "Coumalic acid". Organic Syntheses. 31: 23. doi:10.15227/orgsyn.031.0023.