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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.499 Edit this at Wikidata
UNII
  • 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
  • O=C\1/C=C(\O/C(C(=O)O)=C/1)C(=O)O
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).

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]

See also

References

  1. ^ a b 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.
  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.
  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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