Chelidonic acid explained

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]

Uses

Chelidonic acid is used to synthesize 4-pyrone via thermal decarboxylation.[2]

Natural occurrence

Joseph M. A. Probst (1812–1842) discovered the acid in extracts of Chelidonium majus in 1839[3], and it was first studied by Joseph Udo Lerch (1816–1892) in 1846.[4] [5] It occurs naturally in plants of the Asparagales order.[6] 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.[7] [8]

See also

Notes and References

  1. G. Horvath . C. Russa . Z. Koentoes . J. Gerencser . Synth. Commun. . 1999 . 29 . 21 . 3719–3732 . 10.1080/00397919908086011 . A new Efficient Method for the Preparation of 2,6-Pyridinedihiethyl Ditosylates from Dimethyl 2,60-Pyridinedicarboxylates.
  2. Book: Weygand. Conrad. Hilgetag. G.. Martini. A.. Weygand/Hilgetag Preparative Organic Chemistry. 1972. John Wiley & Sons, Inc.. New York. 0471937495. 1009. 4th.
  3. Probst . 1839 . Beschreibung und Darstellungsweise einiger bei der Analyse des Chelidonium majus neu aufgefundenen Stoffe . Annalen der Pharmacie . de . 29 . 2 . 113–131 . 10.1002/jlac.18390290202 . 1099-0690.
  4. Lerch . J. Ud. . 1846 . Untersuchung der Chelidonsäure . Annalen der Chemie und Pharmacie . de . 57 . 3 . 273–318 . 10.1002/jlac.18460570302 . 1099-0690.
  5. Book: Roscoe. H.E.. Schorlemmer. C.. A Treatise on Chemistry, Volume 3, Part 2. 1890. D Appleton and Company. New York. 624. 1st.
  6. Web site: Asparagales. Angiosperm Phylogeny Website. Angiosperm Phylogeny Group. 30 August 2017.
  7. 10.1016/S0031-9422(98)00134-4. Leaf-opening substance of a nyctinastic plant, Cassia mimosoides. Phytochemistry. 49. 3. 633. 1998. Ueda. Minoru. Ohnuki. Takashi. Yamamura. Shosuke.
  8. Ueda. Minoru. Yamamura. Shosuke. 1998 . Chemical studies on plant movement . Current Organic Chemistry . 2 . 4 . 437–461.

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