Chelidonic acid

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

Chelidonic acid

Names
Systematic 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
3D model (JSmol)	Interactive image
ChemSpider	7153
ECHA InfoCard	100.002.499
PubChem CID	7431
UNII	T33U4W5K6O
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

Chelidonic acid was first discovered in extracts of Chelidonium majus.[4][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

References

1. E. Raymond Riegel and F. Zwilgmeyer (1937). "Chelidonic acid". Organic Syntheses. 17: 40.; Collective Volume, 2, p. 126
2. G. Horvath; C. Russa; Z. Koentoes; J. Gerencser (1999). "A new Efficient Method for the Preparation of 2,6-Pyridinedihiethyl Ditosylates from Dimethyl 2,60-Pyridinedicarboxylates". Synth. Commun. 29 (21): 3719–3732. doi:10.1080/00397919908086011.
3. Weygand, Conrad (1972). Hilgetag, G.; Martini, A. (eds.). Weygand/Hilgetag Preparative Organic Chemistry (4th ed.). New York: John Wiley & Sons, Inc. p. 1009. ISBN 0471937495.
4. Roscoe, H.E.; Schorlemmer, C. (1890). A Treatise on Chemistry, Volume 3, Part 2 (1st ed.). New York: D Appleton and Company. p. 624.
5. Probst, Joseph M. A. (1839) "Beschreibung und Darstellungsweise einiger bei der Analyse des Chelidonium majus aufgefundenen Stoffe" (Description and methods of preparation of some substances found during the analysis of Chelidonium majus), Annalen der Chemie und Pharmacie, 29 (2) : 113–131 ; see especially pp. 116–118.
6. See also: Lerch, Joseph Udo (1846) "Untersuchung der Chelidonsäure" (Investigation of chelidonic acid), Annalen der Chemie und Pharmacie, 57 : 273–318.
7. "Asparagales". Angiosperm Phylogeny Website. Angiosperm Phylogeny Group. Retrieved 30 August 2017.
8. Ueda, Minoru; Ohnuki, Takashi; Yamamura, Shosuke (1998). "Leaf-opening substance of a nyctinastic plant, Cassia mimosoides". Phytochemistry. 49 (3): 633. doi:10.1016/S0031-9422(98)00134-4.
9. Ueda, Minoru; Yamamura, Shosuke (1998). "Chemical studies on plant movement". Current Organic Chemistry. 2 (4): 437–461.