1155-40-4

Basic information

• Product Name: 3,5-DIIODOTHYROACETIC ACID
• Synonyms: 4-(4-HYDROXYPHENOXY)-3,5-DIIODOPHENYLACETIC ACID;3,5-DIIODOTHYROACETIC ACID;THYROACETIC ACID;4-(4-Hydroxyphenoxy)-3,5-diiodobenzeneacetic acid;[4-(p-Hydroxyphenoxy)-3,5-diiodophenyl]acetic Acid;NSC 90463;Levothyroxine Sodium Impurity 14;Benzeneacetic acid,4-(4-hydroxyphenoxy)-3,5-diiodo-
• CAS NO: 1155-40-4
• Molecular Formula: C₁₄H₁₀I₂O₄
• Molecular Weight: 496.04
• EINECS: 214-582-0
• Product Categories: Aromatic Phenylacetic Acids and Derivatives;Aromatics;Drug Analogues;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 1155-40-4.mol

Chemical Properties

• Melting Point: 223.5-225.0 °C(Solv: water (7732-18-5); acetic acid (64-19-7))
• Boiling Point: 527.8°Cat760mmHg
• Flash Point: 273°C
• Appearance: /
• Density: 2.156g/cm³
• Vapor Pressure: 5.7E-12mmHg at 25°C
• Refractive Index: 1.726
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.10±0.10(Predicted)
• CAS DataBase Reference: 3,5-DIIODOTHYROACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DIIODOTHYROACETIC ACID(1155-40-4)
• EPA Substance Registry System: 3,5-DIIODOTHYROACETIC ACID(1155-40-4)

Safety Data

• Hazardous Substances Data: 1155-40-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,5-Diiodo-Thyroxine is used as a pharmaceutical compound for its potent effects on the body's metabolism. It is particularly relevant in the study and treatment of various thyroid-related conditions, as it can mimic or interfere with the action of naturally occurring Thyroxine.
Used in Research and Development:
In the field of research, 3,5-DIT is utilized as a tool to investigate the mechanisms of action and the effects of Thyroxine on cellular and molecular levels. It can be employed to study the role of thyroid hormones in various physiological processes and to develop a better understanding of thyroid-related disorders.
Used in Quality Control and Impurity Testing:
3,5-Diiodo-Thyroxine is used as a reference compound in the quality control and impurity testing of Thyroxine products. It helps ensure the purity and potency of Thyroxine medications, contributing to the overall safety and efficacy of these drugs.
Used in Drug Delivery Systems:
Similar to Gallotannin, 3,5-DIT could potentially be incorporated into drug delivery systems to improve its bioavailability and therapeutic outcomes. This application would require further research and development to optimize the delivery and effectiveness of 3,5-DIT in treating specific conditions.

InChI:InChI=1/C14H10I2O4/c15-11-5-8(7-13(18)19)6-12(16)14(11)20-10-3-1-9(17)2-4-10/h1-6,17H,7H2,(H,18,19)

Upstream product

• 92436-93-6 2-(3,5-diiodo-4-(4-methoxyphenoxy)phenyl)acetic acid 
• 17138-28-2 (4-hydroxy-phenyl)-acetic acid ethyl ester 
• 54291-88-2 methyl 2-(3,5-diiodo-4-(4-methoxyphenoxy)phenyl)acetate 
• 67-30-1 tetrac 
• 94064-21-8 methyl [4-(4-hydroxyphenoxy)-3,5-diiodophenyl]acetate 
• 1948-39-6 (4-hydroxy-3,5-diiodophenyl)acetic acid 
• 56460-36-7 methyl 2-(4-hydroxy-3,5-diiodophenyl)acetate 
• 5720-07-0 4-methoxyphenylboronic acid 
• 101588-11-8 C₁₇H₂₀N₂O₄ 
• 150-76-5 4-methoxy-phenol 
• 123-31-9 hydroquinone 
• 2379-03-5 4-(4-Benzoyloxy-phenoxy)-3,5-dinitro-phenylessigsaeure-ethylester 
• 2444-21-5 (4'-benzyloxyphenyl)benzoate 
• 2444-19-1 4-hydroxyphenyl benzoate 

Downstream Products

• 67-30-1 tetrac 
• 51-24-1 3,3',5-triiodothyroacetic acid 
• 500-79-8 [4-(4-hydroxyphenoxy)phenyl]acetic acid 
• 93013-17-3 [4-(4-hydroxy-phenoxy)-3,5-diiodo-phenyl]-acetic acid ethyl ester 
• 1300559-71-0 methyl {4-[4-(2-chloroethoxy)-3,5-diiodophenoxy]-3,5-diiodophenyl}-acetate 
• 1300559-73-2 Lithium [4-(4-{2-[(diaminomethylene)amino]ethoxy}-3,5-diiodophenoxy)-3,5-diiodophenyl]acetate 
• 1300559-75-4 (4-{4-[2-(carbamoylamino)ethoxy]-3,5-diiodophenoxy}-3,5-diiodophenyl)acetic acid 
• 1300559-77-6 {4-[4-(3-aminopropoxy)-3,5-diiodophenoxy]-3,5-diiodophenyl}acetic acid 
• 1300857-63-9 C₁₈H₁₇I₄NO₄ 
• 1300559-73-2 lithium [4-(4-{2-[(diaminomethylene)amino]-ethoxy}-3,5-diiodophenoxy)-3,5-diiodophenyl]acetate 
• 92060-32-7 [4-(4-hydroxy-3,5-diiodo-phenoxy)-phenyl]-acetic acid 
• 93532-61-7 [4-(4-hydroxy-3-iodo-phenoxy)-phenyl]-acetic acid 
• 92151-25-2 [4-(4-hydroxy-phenoxy)-3,5-diiodo-phenyl]-acetyl azide 
• 92160-59-3 [4-(4-hydroxy-phenoxy)-3,5-diiodo-phenyl]-acetic acid hydrazide 

Relevant articles and documents

Synthesis of MR-49, a deiodinated analog of tetraiodothyroacetic acid (tetrac), as a novel pro-angiogenesis modulator

The tyrosine-based hormones 3,3′,5-triiodo-L-thyronine (L-T3) and L-thyroxine (L-T4) that are produced by the thyroid gland control metabolic functions. Iodothyronine deiodinase enzymes convert L-T4to L-T3, the form of thyroid hormone critical to genomic actions within cells and regulation of metabolism, and to reverse-L-T3, a hormone isoform that is largely inactive. We used tertiary amines in a study of deiodination based on derivatives of tetraiodothyroacetic acid (tetrac)—a naturally occurring derivative of L-T4—to mimic the action of the iodothyronine deiodinases and deiodination of the outer ring iodines. Deiodinated tetrac, MR-49, was found to be pro-angiogenic, with this activity exceeding that of L-T3and L-T4in a hemoglobin Matrigel plug assay of angiogenesis. Tetrac is anti-angiogenic via several nongenomic pathways, and the present studies of MR-49 reveal the critical contribution of outer ring iodines to the angiogenic properties of thyroid hormone analogues, which may have utility as pro-angiogenic pharmaceuticals.

SUBSTITUTED 4-PHENOXYPHENOL ANALOGS AS MODULATORS OF PROLIFERATING CELL NUCLEAR ANTIGEN ACTIVITY

In one aspect, the invention relates to substituted 4-phenoxyphenol analogs, derivatives thereof, and related compounds,which are useful as inhibitors of proliferating cell nuclear antigen (PCNA); synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of treating hyperproliferative disorders associated with PCNA using the compounds and compositions. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention

COMPOSITIONS OF DUAL THYROINTEGRIN ANTAGONISTS AND USE IN VASCULAR-ASSOCIATED DISORDERS

A dual thyrointegrin antagonist and a method for treating an angiogenesis-mediated disorder and/or a hyperthyroidism disorders by introducing the dual thyrointegrin antagonist into animals (e.g., mammals, human beings). The dual thyrointegrin antagonist includes a chemical structure having a thyroid hormone antagonist and alphavbeta3 integrin antagonist in the same molecule

Design, synthesis, and biological evaluation of bifunctional thyrointegrin inhibitors: New anti-angiogenesis analogs

Context: Inhibition of pathological angiogenesis. Objective: Obtaining new transactivator, bifunctional, thyroid antagonist, non-toxic anti-angiogenic compounds. Materials and methods: In silico drug design, synthesis in bulk and biological evaluation in chick chorioallantoic membrane (CAM) model. Results: Significant inhibition (range 6573%) at 0.252.0 g/ml doses. Discussion and conclusion: The synthesis of compounds (9), (10), and (11) incorporating long-chain moieties guanidine, urea, methyl amine and, propyl amine substitutions, respectively, into the core molecular framework of tetrac (tetraiodothyroacetic acid) were undertaken. The evaluation of the anti-angiogenic bioactivity of these compounds in the CAM model revealed no loss of activity in comparison with tetrac and XT199, which showed nearly 86% inhibition at dose levels of 1 and 0.5 g/ml, respectively, and validated the concept.