Chelidonic acid

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.
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 discovered the acid in extracts of Chelidonium majus in 1839, and it was first studied by Joseph [Udo Lerch] 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.