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HomeProduct name listIopanoic acid

Iopanoic acid

Synonym(s):2-(3-Amino-2,4,6-triiodobenzyl)butyric acid;3-(3-Amino-2,4,6-triiodophenyl)-2-ethylpropanoic acid;Iodopanoic acid

  • CAS NO.:96-83-3
  • Empirical Formula: C11H12I3NO2
  • Molecular Weight: 570.93
  • MDL number: MFCD00038687
  • EINECS: 202-539-9
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-10-28 16:48:35
Iopanoic acid  Structural

What is Iopanoic acid ?

Chemical properties

Light Brown Solid

Originator

Telepaque,Winthrop,US,1952

The Uses of Iopanoic acid

antiulcer

The Uses of Iopanoic acid

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

Background

Iopanoic acid contains iodine and is useful as a contrast medium in cholecystography.

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)

Metabolism

Not Available

Properties of Iopanoic acid

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  neat
pka 4.8(at 25℃)
form  Solid
color  Light Brown
Water Solubility  348.3mg/L(37 ºC)
Merck  14,5058
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 information for Iopanoic acid

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P270:Do not eat, drink or smoke when using this product.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P501:Dispose of contents/container to..…

Computed Descriptors for Iopanoic acid

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