Chelidonic acid
Chemical compound
From Wikipedia, the free encyclopedia
Chelidonic acid is a heterocyclic organic acid with a pyran skeleton.
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| Names | |
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| 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 | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.002.499 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| 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).
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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]
Chelidonic acid is one of the most potent inhibitors of glutamate decarboxylase known in vitro, and is thus used in research purpose.[4]
Natural occurrence
Joseph M. A. Probst (1812–1842) discovered the acid in extracts of Chelidonium majus in 1839,[5] and it was first studied by Joseph Udo Lerch (1816–1892) in 1846.[6][7] It occurs naturally in plants of the Asparagales order.[8] 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.[9][10]