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 chemistry is the branch of organic chemistry dealing with the synthesis, properties, and ...

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 rel ...

with a

pyran In chemistry, pyran, or oxine, 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 ...

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 t ...

and

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

: :

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- ...

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 t ...

Natural occurrence

Chelidonic acid was first discovered 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 Ame ...

''. It occurs naturally in plants of the

Asparagales Asparagales (asparagoid lilies) is an order (biology), order of plants in modern classification systems such as the Angiosperm Phylogeny Group (APG) and the Angiosperm Phylogeny Web. The order takes its name from the type (biology), type family ...

order. Potassium chelidonate has been found to be responsible for

nyctinasty Nyctinasty is the circadian rhythmic 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 controlled by the circadian cloc ...

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