60578-17-8

Basic information

• Product Name: 4-(4-hydroxyphenoxy)-3-iodo-Benzeneacetic acid
• Synonyms: 4-(4-hydroxyphenoxy)-3-iodo-Benzeneacetic acid;3-Iodothyroacetic Acid;JDBDXSUPAYTFGB-UHFFFAOYSA-N
• CAS NO: 60578-17-8
• Molecular Formula: C₁₄H₁₁IO₄
• Molecular Weight: 370.13921
• Product Categories: Aromatics, Metabolites & Impurities.
• Mol File: 60578-17-8.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: 4-(4-hydroxyphenoxy)-3-iodo-Benzeneacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-hydroxyphenoxy)-3-iodo-Benzeneacetic acid(60578-17-8)
• EPA Substance Registry System: 4-(4-hydroxyphenoxy)-3-iodo-Benzeneacetic acid(60578-17-8)

Safety Data

• Hazardous Substances Data: 60578-17-8(Hazardous Substances Data)

Usage

Description

4-(4-hydroxyphenoxy)-3-iodo-Benzeneacetic acid is an organic compound characterized by its unique molecular structure, which features a benzene ring with a hydroxyphenoxy group at the 4-position and an iodine atom at the 3-position. 4-(4-hydroxyphenoxy)-3-iodo-Benzeneacetic acid has potential applications in various fields due to its distinct chemical properties.

Uses

Used in Pharmaceutical Industry:
4-(4-hydroxyphenoxy)-3-iodo-Benzeneacetic acid is used as an active pharmaceutical ingredient for its potential therapeutic effects. 4-(4-hydroxyphenoxy)-3-iodo-Benzeneacetic acid's unique structure may allow it to interact with specific biological targets, making it a candidate for the development of new drugs.
Used in Research and Development:
In the field of research and development, 4-(4-hydroxyphenoxy)-3-iodo-Benzeneacetic acid serves as a valuable chemical probe. It can be utilized to study various biological processes and pathways, as well as to develop new methodologies for drug discovery and synthesis.
Used in Diagnostic Applications:
4-(4-hydroxyphenoxy)-3-iodo-Benzeneacetic acid may also find use in diagnostic applications, where it could be employed as a marker or tracer molecule for the detection and monitoring of specific diseases or conditions.
Used in Chemical Synthesis:
As a versatile organic compound, 4-(4-hydroxyphenoxy)-3-iodo-Benzeneacetic acid can be used as a starting material or intermediate in the synthesis of other complex molecules, including pharmaceuticals, agrochemicals, and specialty chemicals.

Upstream product

• 712349-95-6 3-Iodothyronamine 
• 100866-04-4 [3-iodo-4-(4-methoxy-phenoxy)-phenyl]-acetonitrile 
• 100542-63-0 1-(4-chloromethyl-2-iodo-phenoxy)-4-methoxy-benzene 
• 100717-19-9 3-iodo-4-(4-methoxy-phenoxy)-benzyl alcohol 
• 100725-28-8 3-iodo-4-(4-methoxy-phenoxy)-benzaldehyde 
• 101096-67-7 [3-iodo-4-(4-methoxy-phenoxy)-phenyl]-acetic acid 

Downstream Products

• 2229-49-4 4-(4-Hydroxy-phenoxy)-3-iod-phenethylalkohol 
• 92151-30-9 3,3′,5-tetraiodothyroacetic acid 
• 121-26-6 [4-(4-hydroxy-3-iodo-phenoxy)-3-iodo-phenyl]-acetic acid 

Relevant articles and documents

3-Iodothyronamine reduces insulin secretion in vitro via a mitochondrial mechanism

Purpose 3-iodothyronamine (3-T1AM), a decarboxylated and deiodinated thyroid hormone metabolite, leads at pharmacological doses to hypoinsulinemia, hyperglucagonemia and hyperglycemia in vivo. As the pancreatic Langerhans islets express thyroid hormone transmembrane transporters (THTT), we tested the hypothesis that not only plasma membrane-mediated 3-T1AM binding to and activation of G-protein coupled receptors, but also 3-T1AM metabolite(s) generated by 3-T1AM uptake and metabolism might decrease glucose-stimulated insulin secretion (GSIS). Methods Murine pancreatic β-cells MIN6 were characterized for gene expression of THTT, deiodinases and monoamine oxidases. 3-T1AM uptake and intracellular metabolism to the corresponding 3-iodothyroacetic acid were analysed by liquid-chromatography tandem mass spectrometry (LC-MS/MS) at different time points in cells as well as the conditioned medium. Mitochondrial activity, especially ATP-production, was monitored real-time after 3-T1AM application using Seahorse Bioanalyzer technique. Effect of 3-T1AM on GSIS into the culture medium was assayed by ELISA. Results MIN6 cells express classical THTT, proposed to transport 3-T1AM, as well as 3-T1AM metabolizing enzymes comparable to murine primary pancreatic islets. 3-T1AM accumulates in MIN6 cells and is metabolized by intracellular MaoB to 3-iodothyroacetic, which in turn is rapidly exported. 3-T1AM decreases mitochondrial ATP-production concentration dependently. GSIS is diminished by 3-T1AM treatment. Using LC-MS/MS, no further 3-T1AM metabolites except 3-iodothyroacetic were detectable. Conclusions This data provides a first link between cellular 3-T1AM uptake and regulation of mitochondrial energy metabolism in ?-cells, resulting in reduced insulin secretion. We conclude that MIN6 is an appropriate cell model to study 3-T1AM-dependent (intra-)cellular biochemical mechanisms affecting insulin production in vitro.