Chelidonic acid

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 ;
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) (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

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

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]

References

^ ^a ^b E. Raymond Riegel and F. Zwilgmeyer (1937). "Chelidonic acid". Organic Syntheses. 17: 40; Collected Volumes, vol. 2, p. 126.
^ 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.
^ 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.
^ Probst (1839). "Beschreibung und Darstellungsweise einiger bei der Analyse des Chelidonium majus neu aufgefundenen Stoffe". Annalen der Pharmacie (in German). 29 (2): 113–131. doi:10.1002/jlac.18390290202. ISSN 1099-0690.
^ Lerch, J. Ud. (1846). "Untersuchung der Chelidonsäure". Annalen der Chemie und Pharmacie (in German). 57 (3): 273–318. doi:10.1002/jlac.18460570302. ISSN 1099-0690.
^ Roscoe, H.E.; Schorlemmer, C. (1890). A Treatise on Chemistry, Volume 3, Part 2 (1st ed.). New York: D Appleton and Company. p. 624.
^ "Asparagales". Angiosperm Phylogeny Website. Angiosperm Phylogeny Group. Retrieved 30 August 2017.
^ 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.
^ Ueda, Minoru; Yamamura, Shosuke (1998). "Chemical studies on plant movement". Current Organic Chemistry. 2 (4): 437–461.

[OrgSynth-1] E. Raymond Riegel and F. Zwilgmeyer (1937). "Chelidonic acid". Organic Syntheses. 17: 40; Collected Volumes, vol. 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.

[Weygand-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] Probst (1839). "Beschreibung und Darstellungsweise einiger bei der Analyse des Chelidonium majus neu aufgefundenen Stoffe". Annalen der Pharmacie (in German). 29 (2): 113–131. doi:10.1002/jlac.18390290202. ISSN 1099-0690.

[5] Lerch, J. Ud. (1846). "Untersuchung der Chelidonsäure". Annalen der Chemie und Pharmacie (in German). 57 (3): 273–318. doi:10.1002/jlac.18460570302. ISSN 1099-0690.

[Treatise-6] Roscoe, H.E.; Schorlemmer, C. (1890). A Treatise on Chemistry, Volume 3, Part 2 (1st ed.). New York: D Appleton and Company. p. 624.

[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.

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Preparation

Uses

Natural occurrence

See also

References