Chelidonic_acid

Chelidonic acid

Chelidonic acid

Chemical compound

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

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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]

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

References

  1. [1]
    E. Raymond Riegel and F. Zwilgmeyer (1937). "Chelidonic acid". Organic Syntheses. 17: 40; Collected Volumes, vol. 2, p. 126.
  2. [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. [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. [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. [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. [6]
    See also: Lerch, Joseph Udo (1846) "Untersuchung der Chelidonsäure" (Investigation of chelidonic acid), Annalen der Chemie und Pharmacie, 57 : 273–318.
  7. [7]
    "Asparagales". Angiosperm Phylogeny Website. Angiosperm Phylogeny Group. Retrieved 30 August 2017.
  8. [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. [9]
    Ueda, Minoru; Yamamura, Shosuke (1998). "Chemical studies on plant movement". Current Organic Chemistry. 2 (4): 437–461.
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