2052. Chelidonic Acid

Nomenclature

CAS number: 99-32-1
4-Oxo-4H-pyran-2,6-dicarboxylic acid; 4-oxo-1,4-pyran-2,6-dicarboxylic acid; Jerva acid; jervasic acid.
C7H4O6; mol wt 184.10.
C 45.67%, H 2.19%, O 52.14%.

Description and references

Presence in various plants: Stransky, Arch. Pharm. 258, 56 (1920); Ramstad, Pharm. Acta Helv. 28, 45 (1953). Structure: Verkade, Recl. Trav. Chim. Pays-Bas 43, 879 (1924). Synthesis: Riegel, Reinhard, J. Am. Chem. Soc. 48, 1334 (1926); Riegel, Zwilgmeyer, Org. Synth. coll. vol. II, 126 (1943); Toomey, Riegel, J. Org. Chem. 17, 1492 (1952).

Chemical structure

Properties

Crystals, dec 257°. uv max (water): 270 nm (ε 11500). One gram dissolves in 65 ml water, 26 ml boiling water. Sparingly sol in alc.

Derivative

Monohydrate.

Properties

Monoclinic crystals from hot alcohol + water. The water of crystn is given up when heated at 102° and then at 160° to constant weight.

Derivative

Sodium salt.

Properties

Sparingly sol in water.