Misplaced Pages

Chelidonic acid

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.499 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
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
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 , 100 kPa). Infobox references
Chemical compound

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:

Uses

Chelidonic acid is used to synthesize 4-pyrone via thermal decarboxylation.

Natural occurrence

Joseph M. A. Probst (1812–1842) discovered the acid in extracts of Chelidonium majus in 1839, and it was first studied by Joseph Udo Lerch (1816–1892) in 1846. It occurs naturally in plants of the Asparagales order. 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.

See also

References

  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.
  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.
Categories:
Chelidonic acid Add topic