Chelidonic acid

Preparation

Chelidonic acid can be prepared in two steps from diethyl oxalate and acetone:

:[[File:Chelidonic_Acid_Synthesis.svg|left|600px]]

Uses

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

Chelidonic acid is one of the most potent inhibitors of glutamate decarboxylase known in vitro, and is thus used in research purpose.

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.

References

References

1. E. Raymond Riegel and F. Zwilgmeyer. (1937). "Chelidonic acid".
2. (1999). "A new Efficient Method for the Preparation of 2,6-Pyridinedihiethyl Ditosylates from Dimethyl 2,60-Pyridinedicarboxylates". Synth. Commun..
3. (1972). "Weygand/Hilgetag Preparative Organic Chemistry". John Wiley & Sons, Inc..
4. (1985). "Chelidonic acid and other conformationally restricted substrate analogues as inhibitors of rat brain glutamate decarboxylase". Biochemical Pharmacology.
5. Probst. (1839). "Beschreibung und Darstellungsweise einiger bei der Analyse des Chelidonium majus neu aufgefundenen Stoffe". Annalen der Pharmacie.
6. Lerch, J. Ud.. (1846). "Untersuchung der Chelidonsäure". Annalen der Chemie und Pharmacie.
7. (1890). "A Treatise on Chemistry, Volume 3, Part 2". D Appleton and Company.
8. "Asparagales". Angiosperm Phylogeny Group.
9. (1998). "Leaf-opening substance of a nyctinastic plant, Cassia mimosoides". Phytochemistry.
10. (1998). "Chemical studies on plant movement". Current Organic Chemistry.