Chelidonic acid

Chelidonic acid is a heterocyclic organic acid with a pyran skeleton.

Chelidonic acid

Names
Preferred IUPAC name 4-Oxo-4H-pyran-2,6-dicarboxylic acid
Other names Jerva acid; Jervaic acid; Jervasic acid; γ-Pyrone-2,6-dicarboxylic acid
Identifiers
CAS Number	99-32-1 Y
3D model (JSmol)	Interactive image
ChemSpider	7153
ECHA InfoCard	100.002.499
PubChem CID	7431
UNII	T33U4W5K6O Y
CompTox Dashboard (EPA)	DTXSID30243928
InChI InChI=1S/C7H4O6/c8-3-1-4(6(9)10)13-5(2-3)7(11)12/h1-2H,(H,9,10)(H,11,12) Key: PBAYDYUZOSNJGU-UHFFFAOYSA-N InChI=1/C7H4O6/c8-3-1-4(6(9)10)13-5(2-3)7(11)12/h1-2H,(H,9,10)(H,11,12) Key: PBAYDYUZOSNJGU-UHFFFAOYAH
SMILES O=C\1/C=C(\O/C(C(=O)O)=C/1)C(=O)O
Properties
Chemical formula	C7H4O6
Molar mass	184.103 g·mol−1
Melting point	257 °C (495 °F; 530 K)[1] (decomposes)
Related compounds
Related compounds	Meconic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Preparation

Chelidonic acid can be prepared in two steps from diethyl oxalate and acetone:^[1][2]

Uses

Chelidonic acid is used to synthesize 4-pyrone via thermal decarboxylation.^[3]

Natural occurrence

Joseph M. A. Probst (1812–1842) discovered the acid in extracts of Chelidonium majus in 1839,^[4] and it was first studied by Joseph Udo Lerch (1816–1892) in 1846.^[5][6] It occurs naturally in plants of the Asparagales order.^[7] Potassium chelidonate has been found to be responsible for nyctinasty in some plants; specifically, it has been found to regulate the closing of leaves of Cassia mimosoides at nightfall.^[8][9]

See also

• Dimethyl oxalate
• Dehydroacetic acid