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ALPHA-ETHYL-3-HYDROXY-2,4,6-TRIIODOHYDROCINNAMIC ACID

CAS No.
96-84-4
Chemical Name:
ALPHA-ETHYL-3-HYDROXY-2,4,6-TRIIODOHYDROCINNAMIC ACID
Synonyms
teridax;Jodoprol;Iophenoic;Tiloshade;Trilombrine;IophenoicAcid;IOPHENOXIC ACID;triiodoethionicacid;alpha-ethyl-beta-(3-hydrox;Acide iophenoique [INN-French]
CBNumber:
CB5266250
Molecular Formula:
C11H11I3O3
Molecular Weight:
571.92
MDL Number:
MFCD00133419
MOL File:
96-84-4.mol
Last updated:2023-05-04 17:34:44

ALPHA-ETHYL-3-HYDROXY-2,4,6-TRIIODOHYDROCINNAMIC ACID Properties

Melting point 146-148 °C (lit.)
Boiling point 459.0±45.0 °C(Predicted)
Density 2.2890 (estimate)
pka pKa 7.5(H2O,(extrap)) (Uncertain)
Merck 13,5077
FDA UNII 73TJC7JGUY

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
Hazard Codes  Xn
Risk Statements  22-36/37/38
Safety Statements  26-37/39
WGK Germany  3
RTECS  MW5280000
Toxicity LD50 i.v. in mice: 374 mg/kg (Hoppe)

ALPHA-ETHYL-3-HYDROXY-2,4,6-TRIIODOHYDROCINNAMIC ACID price More Price(2)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 361046 α-Ethyl-3-hydroxy-2,4,6-triiodohydrocinnamic acid 97% 96-84-4 5g $216 2024-03-01 Buy
American Custom Chemicals Corporation HCH0066813 ALPHA-ETHYL-3-HYDROXY-2,4,6-TRIIODOHYDROCINNAMIC ACID 95.00% 96-84-4 5G $1164.14 2021-12-16 Buy
Product number Packaging Price Buy
361046 5g $216 Buy
HCH0066813 5G $1164.14 Buy

ALPHA-ETHYL-3-HYDROXY-2,4,6-TRIIODOHYDROCINNAMIC ACID Chemical Properties,Uses,Production

Originator

Teridax,Schering

Uses

α-Ethyl-3-hydroxy-2,4,6-triiodohydrocinnamic acid (iophenoxic acid ) was used as marker in “bait acceptance” studies conducted on various animal species. It was used in the direct quantitation of iophenoxic acid in porcine serum samples by a liquid chromatographic-electrospray ionization mass spectrometric technique.

Definition

ChEBI: Iophenoic acid is a member of benzenes and a monocarboxylic acid.

Manufacturing Process

A mixture of m-hydroxy-benzaldehyde, fused sodium propionate and of butyric anhydride was stirred and refluxed at heating.
The mixture was then poured into water and acidified with hydrochloric acid. The organic material was extracted with chloroform, the chloroform was exaporated, and the residue stirred for one and 1.5 h with dilute potassium hydroxide solution. Acetic acid was added to make the solution almost neutral, but still slightly basic, the mixture was stirred with activated charcoal for about 15 min, filtered, and the filtrate acidified to Congo red with hydrochloric acid. A crystalline product was obtained upon cooling for several hours, and this was collected by filtration and recrystallized from water giving α-ethyl-mhydroxycinnamic acid.
A solution of α-ethyl-m-hydroxycinnamic acid and potassium hydroxide in water was added to 3% sodium amalgam, and the mixture was stirred while heating on a steam bath for several hours. The mixture was then cooled, the mercury separated, and the reaction mixture was acidified and extracted with ether. The ether extracts were concentrated giving a residue containing α- ethyl-β-(m-hydroxyphenyl)propionic acid.
α-Ethyl-β-(m-hydroxyphenyl)propionic acid was dissolved in acetic acid. The solution was warmed on a steam bath, and water was added followed iodine monochloride. The mixture was stirred and heated for several hours, and water was then added to cause precipitation of the product. The semi-solid precipitate was triturated with a small amount of 95% alcohol, collected by filtration and washed with low boiling petroleum ether. Recrystallization from dilute alcohol, using charcoal for decolorization, gave α-ethyl-β-(2,4,6-triiodo- 3-hydroxyphenyl)propionic acid.

brand name

Teridax (Schering).

Therapeutic Function

Diagnostic aid

General Description

α-Ethyl-3-hydroxy-2,4,6-triiodohydrocinnamic acid (Iophenoxic acid ) is an organic, iodine-containing compound. Iophenoxic acid is an iodinated radiocontrast agent, its clinical use has been withdrawn due to its exceptionally long half-life in the body, since it has high-affinity binding to human serum albumin (HSA). Structural basis of its interaction with HSA has been evaluated.

ALPHA-ETHYL-3-HYDROXY-2,4,6-TRIIODOHYDROCINNAMIC ACID Preparation Products And Raw materials

ALPHA-ETHYL-3-HYDROXY-2,4,6-TRIIODOHYDROCINNAMIC ACID Suppliers

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IOPHENOXIC ACID ALPHA-ETHYL-3-HYDROXY-2,4,6-TRIIODOHYDROCINNAMIC ACID alpha-(2,4,6-triiodo-3-hydroxybenzyl)butyricacid alpha-ethyl-3-hydroxy-2,4,6-triiodo-hydrocinnamicaci alpha-ethyl-beta-(3-hydroxy-2,4,6-triiodophenyl)propionicacid teridax triiodoethionicacid Iophenoic α-ethyl-3-hydroxy-2,4,6-triiodohydrocinnamic acid Acide iophenoique [INN-French] IophenoicAcid Jodoprol Tiloshade Trilombrine 2-(3-hydroxy-2,4,6-triiodo-benzyl)butyric acid 2-[(3-hydroxy-2,4,6-triiodophenyl)methyl]butanoic acid 2-[(3-hydroxy-2,4,6-triiodo-phenyl)methyl]butanoic acid 2-(3-hydroxy-2,4,6-triiodobenzyl)butanoic acid Benzenepropanoic acid, a-ethyl-3-hydroxy-2,4,6-triiodo- Benzenepropanoic acid, α-ethyl-3-hydroxy-2,4,6-triiodo- alpha-ethyl-beta-(3-hydrox α-Ethyl-3-hydroxy-2,4,6-triiodohydrocinnamic acid 96-84-4 HOC6HI3CH2CHC2H5CO2H C11H11I3O3 Organic Building Blocks Carbonyl Compounds Carboxylic Acids C11 to C12 Building Blocks