Introduction：Basic information about Iopanoic acid CAS 96-83-3, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
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 |
| pka | 4.8(at 25℃) |
| form | Solid |
| color | Light Brown |
| Water Solubility | 348.3mg/L(37 ºC) |
| Merck | 14,5058 |
| BCS Class | 2 |
| Major Application | pharmaceutical (small molecule) |
| InChI | 1S/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) |
| InChIKey | OIRFJRBSRORBCM-UHFFFAOYSA-N |
| SMILES | O=C(O)C(CC)CC1=C(I)C(N)=C(I)C=C1I |
| 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
| Risk Statements | 20/21/22 |
| Safety Statements | 22-26-36/37/39 |
| WGK Germany | 1 |
| RTECS | NW5075000 |
| HS Code | 2922.49.3700 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral |
| Hazardous Substances Data | 96-83-3(Hazardous Substances Data) |
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 from100 g of m-nitrobenzaldehyde, 210 g of butyric anhydride and 73 g of sodiumbutyrate. The crude α-ethyl-m-nitrocinnamicacid is crystallized from ethanolgiving about 105 g, MP 140° to 142°C. From the filtrates there may beisolated a small amount of a stereoisomer, which when pure melts at 105° to106°C.
(B) Preparation of m-Amino-α-Ethylhydrocinnamic Acid: A mixture of 50 g ofα-ethyl-m-nitrocinnamic acid, 9.1 g of sodium hydroxide, 600 cc of water and5 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 ofhydrogen 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 uponstanding, giving about 20 g, MP 60° to 68°C. Complete evaporation of thefiltrate and extraction of the residue of inorganic salts with ether gives about20 g of additional material, MP 54° to 59°C. Recrystallization of the combinedproduct 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: Asolution of 5.0 g of m-amino-α-ethylhydrocinnamic acid in 100 cc of watercontaining 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 waterand 25 cc of concentrated hydrochloric acid heated to 60°C. After addition iscomplete, the heating is continued for one hour longer at 60° to 70°C. A blackoil 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° to150°C. The β-(3-amino-2,4,6-triiodophenyl)-α-ethylpropionic acid may bepurified further by precipitation of the morpholine salt from ether solution andregeneration of the free amino acid by treatment of a methanol solution of themorpholine salt with sulfur dioxide. The pure amino acid has the MP 155° to156.5°C. |
| Therapeutic Function | Diagnostic aid (radiopaque medium) |
Iopanoic acid Preparation Products And Raw materials
| Raw materials | Aluminum-->Dichloroethane-->Ethylbenzene-->KAOLIN-->3-Nitrobenzaldehyde-->Aluminium-nickel-->Butyric anhydride-->Iodic acid-->Sodium Butyrate-->3-Phenylpropionic acid-->Iodine monochloride-->Hydrogen |
