5026. Iodoalphionic Acid

Nomenclature

CAS number: 577-91-3
4-Hydroxy-3,5-diiodo-α-phenylbenzenepropanoic acid; β-(4-hydroxy-3,5-diiodophenyl)-α-phenylpropionic acid; 3,5-diiodo-α-phenylphloretic acid; Coletrast; Priodax (Schering); Pheniodol; Dikol; Iodobil; Jodobil; Biliognost; Tenicid; Biliselectan.
C15H12I2O3; mol wt 494.06.
C 36.47%, H 2.45%, I 51.37%, O 9.72%.

Description and references

Prepd by iodinating β-(4-hydroxyphenyl)-α-phenylpropionic acid with iodine in an aq soln of alkali iodide in the presence of NH3 or with iodine in acetic anhydride as the iodinating agent, cf. GB 559024 (1944), C.A. 40, 1883 (1946). Prepn of optically active forms: Tullar, Hoppe, US 2552696 (1951 to Sterling Drug). Toxicity data: J. O. Hoppe, S. Archer, Am. J. Roentgenol. Radium Ther. 69, 630 (1953).

Chemical structure

Derivative

dl-Form.

Properties

Faintly yellowish powder. dec 157-162°. Crystals from acetic acid, mp 163.5-163.8°. Insol in water. Sol in alcohol, ether, alkali carbonate and in alkali hydroxide solns; slightly sol in benzene and chloroform. Forms a water-sol disodium salt. LD50 in mice (g/kg): 3.8 orally (Hoppe, Archer).

Derivative

l-Form.

Properties

Hydrated crystals, mp 80-85°, [α]D25 59° (c = 1.5 in 95% alcohol).

Derivative

l-Form disodium salt.

Properties

mp >230°, [α]D26 56.6° (c = 1.5 in water).

Derivative

d-Form.

Properties

Hydrated crystals, mp 80-85°, [α]D25 +59° (c = 1.5 in 95% alcohol).

Derivative

d-Form disodium salt.

Properties

mp >230°, [α]D26 +56.6° (c = 1.5 in water).

Therapeutic Category

Diagnostic aid (radiopaque medium—cholecystographic).

Keywords

Diagnostic Aid (Radiopaque Medium)