96-84-4

Usage

Uses

Used in Animal Behavior Studies:
ALPHA-ETHYL-3-HYDROXY-2,4,6-TRIIODOHYDROCINNAMIC ACID is used as a marker in "bait acceptance" studies for understanding the feeding preferences and behaviors of various animal species. Its distinctive chemical properties allow researchers to track and analyze the consumption patterns of animals, providing valuable insights into their ecological and physiological needs.
Used in Analytical Chemistry:
In the field of analytical chemistry, ALPHA-ETHYL-3-HYDROXY-2,4,6-TRIIODOHYDROCINNAMIC ACID is used for the direct quantitation of iophenoxic acid in porcine serum samples. A liquid chromatographic-electrospray ionization mass spectrometric technique is employed to accurately measure its concentration, which is crucial for assessing the bioavailability and pharmacokinetics of the compound in biological systems.
These applications highlight the versatility of ALPHA-ETHYL-3-HYDROXY-2,4,6-TRIIODOHYDROCINNAMIC ACID in both scientific research and practical applications, making it an important compound for further exploration and development.

Originator

Teridax,Schering

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.

InChI:InChI=1/C11H11I3O3/c1-2-5(11(16)17)3-6-7(12)4-8(13)10(15)9(6)14/h4-5,15H,2-3H2,1H3,(H,16,17)

Upstream product

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Relevant academic research and scientific papers

Pd-Catalyzed β-C(sp3)?H Arylation of Propionic Acid and Related Aliphatic Acids

A generally applicable Pd-catalyzed protocol for the β-C(sp3)?H arylation of propionic acid and related α-branched aliphatic acids is reported. Enabled by the use of N-acetyl-β-alanine as ligand our protocol delivers a broad range of arylation products. Notably, the highly challenging substrate, propionic acid, which lacks any acceleration through the Thorpe–Ingold effect, can be employed as substrate with synthetically useful yields. Furthermore, the scalability and synthetic applicability of the protocol are demonstrated.