258. Allantoin

Nomenclature

CAS number: 97-59-6
(2,5-Dioxo-4-imidazolidinyl)urea; 5-ureidohydantoin; glyoxyldiureide; cordianine.
C4H6N4O3; mol wt 158.12.
C 30.38%, H 3.82%, N 35.43%, O 30.36%.

Description and references

Product of purine metabolism. Prepd synthetically by the oxidation of uric acid with alkaline potassium permanganate: Org. Synth. coll. vol. II, 23 (1943). By heating urea with dichloroacetic acid: C. N. Zellner, J. R. Stevens, US 2158098 (1939 to Merck & Co.) Acetyl derivs: Biltz, Loewe, J. Prakt. Chem. 141, 291 (1934). Optically active forms have been obtained by extraction procedures.

Chemical structure

Properties

White crystalline powder, mp 225° (dec). Slightly sol in water; very slightly sol in alcohol.

Derivative

Racemic Form.

Properties

Monoclinic plates or prisms from water, mp 238°. One gram dissolves in 190 ml water, 500 ml alcohol; more sol in hot water and hot alcohol. Almost insol in ether. pH of satd water soln: 5.5.

Therapeutic Category

Vulnerary.

Therapeutic Category (Veterinary)

Vulnerary; debriding agent.

Keywords

Topical Protectant; Vulnerary