Iopanoic acid Property

Melting point:

153 °C

Boiling point:

529.1±50.0 °C(Predicted)

Density 

2.2567 (estimate)

storage temp. 

2-8°C

solubility 

DMSO, Methanol

form 

Solid

pka

4.8(at 25℃)

color 

Light Brown

Water Solubility 

348.3mg/L(37 ºC)

Merck 

14,5058

BCS Class

2

CAS DataBase Reference

96-83-3(CAS DataBase Reference)

EPA Substance Registry System

Benzenepropanoic acid, 3-amino-.alpha.-ethyl-2,4,6-triiodo- (96-83-3)

Safety

Risk Statements 

20/21/22

Safety Statements 

22-26-36/37/39

WGK Germany 

1

RTECS 

NW5075000

HS Code 

2922.49.3700

Hazardous Substances Data

96-83-3(Hazardous Substances Data)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

Iopanoic acid Chemical Properties,Usage,Production

Chemical Properties

Light Brown Solid

Originator

Telepaque,Winthrop,US,1952

Uses

antiulcer

Uses

Iodopanoic Acid is an iodine-containing radiocontrast medium used in cholecystography. Iodopanoic Acid is a potent inhibitor of thyroid hormone release from thyroid gland.

Definition

ChEBI: Iopanoic acid is a monocarboxylic acid.

Manufacturing Process

(A) Preparation of α-Ethyl-m-Nitrocinnamic Acid: This acid is prepared from 100 g of m-nitrobenzaldehyde, 210 g of butyric anhydride and 73 g of sodium butyrate. The crude α-ethyl-m-nitrocinnamicacid is crystallized from ethanol giving about 105 g, MP 140° to 142°C. From the filtrates there may be isolated a small amount of a stereoisomer, which when pure melts at 105° to 106°C.
(B) Preparation of m-Amino-α-Ethylhydrocinnamic Acid: A mixture of 50 g of α-ethyl-m-nitrocinnamic acid, 9.1 g of sodium hydroxide, 600 cc of water and 5 teaspoons of Raney nickel catalyst is shaken at 32°C in an atmosphere ofhydrogen at an initial pressure of 450 psi until the calculated amount of hydrogen is absorbed. The filtered solution is acidified with hydrochloric acid, made basic with ammonium hydroxide and again acidified with acetic acid. Upon concentration of this solution, an oil separates which crystallizes upon standing, giving about 20 g, MP 60° to 68°C. Complete evaporation of the filtrate and extraction of the residue of inorganic salts with ether gives about 20 g of additional material, MP 54° to 59°C. Recrystallization of the combined product from benzene petroleum ether gives about 35 g of m-amino-α- ethylhydrocinnamic acid, MP 67° to 70°C.
(C) Preparation of β-(3-Amino-2,4,6-Triiodophenyll-α-Ethylpropionic Acid: A solution of 5.0 g of m-amino-α-ethylhydrocinnamic acid in 100 cc of water containing 5 cc of concentrated hydrochloric acid is added over a period of ? hour to a stirred solution of 3.2 cc of iodine monochloride in 25 cc of water and 25 cc of concentrated hydrochloric acid heated to 60°C. After addition is complete, the heating is continued for one hour longer at 60° to 70°C. A black oil separates which gradually solidifies.
The mixture is then cooled and sodium bisulfite added to decolorize. Recrystallization of the product from methanol gives about 8 g, MP 147° to 150°C. The β-(3-amino-2,4,6-triiodophenyl)-α-ethylpropionic acid may be purified further by precipitation of the morpholine salt from ether solution and regeneration of the free amino acid by treatment of a methanol solution of the morpholine salt with sulfur dioxide. The pure amino acid has the MP 155° to 156.5°C.

Therapeutic Function

Diagnostic aid (radiopaque medium)