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Iopanoic acid

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Iopanoic acid Basic information

Product Name:
Iopanoic acid
Synonyms:
  • 3-amino-alpha-ethyl-2,4,6-triiodo-benzenepropanoicaci
  • 3-amino-alpha-ethyl-2,4,6-triiodobenzenepropanoicacid
  • 3-amino-alpha-ethyl-2,4,6-triiodo-hydrocinnamicaci
  • 3-Amino-ethyl-2,4,6-triiodobenaenepropanoicacid
  • 3-Amino-ethyl-2,4,6-triiodohydrocinnamicacid
  • beta-(3-amino-2,4,6-triiodophenyl)-alpha-ethylpropionicacid
  • bilijodon
  • choladine
CAS:
96-83-3
MF:
C11H12I3NO2
MW:
570.93
EINECS:
202-539-9
Product Categories:
  • PREVACID
Mol File:
96-83-3.mol
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Iopanoic acid Chemical Properties

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)
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Safety Information

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)
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Iopanoic acid Usage And Synthesis

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)

Iopanoic acid Supplier

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