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

Safety Information

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)

MSDS

• Language:English Provider:SigmaAldrich

ALPHA-ETHYL-3-HYDROXY-2,4,6-TRIIODOHYDROCINNAMIC ACID Usage And Synthesis

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(96-84-4)Related Product Information

• Diclofenac sodium
• Terbinafine Hydrochloride
• 1-IODO-4-N-PROPYLBENZENE
• 1-(4'-IODOPHENYL)BUTANE
• 1,3,5-TRIIODOBENZENE
• 3-(2-IODOPHENYL)PROPIONIC ACID
• 4-Iodophenol
• 2-ETHYLIODOBENZENE
• 3-ETHYL-4-IODOPHENOL
• 4-IODO-3-METHYL-PHENOL
• 2,4,6-Triiodophenol
• 2,4-DIIODOPHENOL
• ALPHA-ETHYL-3-HYDROXY-2,4,6-TRIIODOHYDROCINNAMIC ACID
• 2-(3-HYDROXY-BENZYL)-BUTYRIC ACID
• 3-(4-IODOPHENYL)PROPIONIC ACID