Chelidonic acid is a

heterocyclic A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, proper ...

organic acid An organic acid is an organic compound with acidic properties. The most common organic acids are the carboxylic acids, whose acidity is associated with their carboxyl group –COOH. Sulfonic acids, containing the group –SO2OH, are re ...

with a

pyran In chemistry, pyran is a six-membered heterocyclic, non-aromatic ring, consisting of five carbon atoms and one oxygen atom and containing two double bonds. The molecular formula is C5H6O. There are two isomers of pyran that differ by the location ...

skeleton.

Preparation

Chelidonic acid can be prepared in two steps from

diethyl oxalate In organic chemistry, an ethyl group (abbr. Et) is an alkyl substituent with the formula , derived from ethane (). ''Ethyl'' is used in the International Union of Pure and Applied Chemistry's nomenclature of organic chemistry for a saturated ...

and

acetone Acetone (2-propanone or dimethyl ketone) is an organic compound with the chemical formula, formula . It is the simplest and smallest ketone (). It is a colorless, highly Volatile organic compound, volatile, and flammable liquid with a charact ...

: :

Uses

Chelidonic acid is used to synthesize

4-pyrone 4-Pyrone (γ-pyrone or pyran-4-one) is an unsaturated cyclic chemical compound with the molecular formula C5H4O2.It is isomeric with 2-pyrone. Preparation 4-Pyrone is prepared via the thermal decarboxylation of chelidonic acid. Reactions 4-Pyr ...

via thermal

decarboxylation Decarboxylation is a chemical reaction that removes a carboxyl group and releases carbon dioxide (CO2). Usually, decarboxylation refers to a reaction of carboxylic acids, removing a carbon atom from a carbon chain. The reverse process, which is ...

Natural occurrence

Joseph M. A. Probst (1812–1842) discovered the acid in extracts of ''

Chelidonium majus ''Chelidonium majus'', the greater celandine, is a perennial herbaceous flowering plant in the poppy family Papaveraceae. One of two species in the genus '' Chelidonium'', it is native to Europe and western Asia and introduced widely in North Am ...

'' in 1839, and it was first studied by Joseph Udo Lerch (1816–1892) in 1846. It occurs naturally in plants of the

Asparagales Asparagales (asparagoid lilies) are a diverse order of flowering plants in the monocots. Under the APG IV system of flowering plant classification, Asparagales are the largest order of monocots with 14 families, 1,122 genera, and about 36,00 ...

order. Potassium chelidonate has been found to be responsible for

nyctinasty In plant biology, nyctinasty is the circadian rhythm-based nastic movement of higher plants in response to the onset of darkness, or a plant "sleeping". Nyctinastic movements are associated with diurnal light and temperature changes and con ...

in some plants; specifically, it has been found to regulate the closing of leaves of ''Cassia mimosoides'' at nightfall.

References

{{reflist 4-Pyrones Dicarboxylic acids

Preparation

Uses

Natural occurrence

See also

References