96-83-3 Usage
Description
Iopanoic acid, also known as Iodopanoic acid, is an iodine-containing organic compound with the chemical formula C11H6I2NO4. It is a water-soluble, yellow crystalline solid that is soluble in organic solvents. Iopanoic acid is known for its strong chelating properties and its ability to bind with metal ions, particularly those of iodine. This characteristic makes it a valuable compound in various applications, particularly in the medical field.
Uses
Used in Medical Imaging:
Iopanoic acid is used as a radiocontrast medium for cholecystography, a diagnostic imaging procedure that visualizes the gallbladder and bile ducts. The iodine content in Iopanoic acid enhances the contrast between the gallbladder and surrounding tissues, allowing for better visualization and diagnosis of any abnormalities.
Used in Thyroid Function Regulation:
Iopanoic acid is used as a potent inhibitor of thyroid hormone release from the thyroid gland. Its chelating properties enable it to bind with iodine ions, thereby reducing the amount of available iodine for hormone synthesis. This action helps in the management of hyperthyroidism and other thyroid-related disorders by controlling the production and release of thyroid hormones.
Originator
Telepaque,Winthrop,US,1952
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)
Check Digit Verification of cas no
The CAS Registry Mumber 96-83-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 6 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 96-83:
(4*9)+(3*6)+(2*8)+(1*3)=73
73 % 10 = 3
So 96-83-3 is a valid CAS Registry Number.
InChI:InChI=1/C11H12I3NO2/c1-2-5(11(16)17)3-6-7(12)4-8(13)10(15)9(6)14/h4-5H,2-3,15H2,1H3,(H,16,17)