Tiratricol

Base Information

• Chemical Name: Tiratricol
• CAS No.: 51-24-1
• Molecular Formula: C14H9I3O4
• Molecular Weight: 621.937
• Hs Code.: 2918990090
• European Community (EC) Number: 200-086-1
• NSC Number: 759294
• UNII: 29OQ9EU4R1
• DSSTox Substance ID: DTXSID2045232
• Nikkaji Number: J4.113K
• Wikipedia: Tiratricol
• Wikidata: Q7809151
• NCI Thesaurus Code: C66605
• Pharos Ligand ID: FP9NJ83YGN4F
• Metabolomics Workbench ID: 148106
• ChEMBL ID: CHEMBL41632
• Mol file: 51-24-1.mol

Synonyms:3,3',5-triiodothyroacetic acid;3,3',5-triiodothyroacetic acid, sodium salt;3,5,3'-triiodothyroacetic acid;3,5-diiodo-3'-isopropylthyroacetic acid;Téatrois;tiratricol;Triac;Triacana

Chemical Property of Tiratricol

Chemical Property:

• Vapor Pressure: 3.92E-12mmHg at 25°C
• Melting Point: 181.5 °C
• Refractive Index: 1.766
• Boiling Point: 531.6 °C at 760 mmHg
• PKA: 4.02±0.10(Predicted)
• Flash Point: 275.3 °C
• PSA: 66.76000
• Density: 2.467 g/cm³
• LogP: 4.62540
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly, Heated, Sonicated)
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 621.7635
• Heavy Atom Count: 21
• Complexity: 356

Purity/Quality:

99% ^*data from raw suppliers

3,3',5-Triiodothyroacetic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C=C1OC2=C(C=C(C=C2I)CC(=O)O)I)I)O
• Recent ClinicalTrials: Withdrawal of Tiratricol Treatment in Males With Monocarboxylate Transporter 8 Deficiency (MCT8 Deficiency)
• Recent EU Clinical Trials: Withdrawal of Tiratricol Treatment in Males with Monocarboxylate Transporter 8 Deficiency (MCT8 Deficiency): A Double blind, Randomized, Placebo controlled Study
• Uses: 3,3'',5-Triiodo Thyroacetic Acid (T3-Acetic Acid (USP)) is a thyroid hormone analogue. A potent Thyroxine impurity. Levothyroxine EP Impurity C. Thyroid hormone analogue thyroid agent
• Therapeutic Function: Thyroid hormone

Technology Process of Tiratricol

There total 4 articles about Tiratricol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2-(4-(4-hydroxyphenoxy)-3,5-diiodophenyl)acetic acid (1155-40-4) → 3,3',5-triiodothyroacetic acid (51-24-1)

Guidance literature:

With ammonia; anschliessendes Behandeln mit wss. Jod-KI-Loesung;

DOI:10.1007/BF03019874

Reference yield:

[3,5-diiodo-4-(4-methoxy-phenoxy)-phenyl]-acetic acid ethyl ester (85828-82-6) → 3,3',5-triiodothyroacetic acid (51-24-1)

Guidance literature:

Multi-step reaction with 2 steps

1: aqueous HI; red phosphorus; acetic acid

2: aqueous methanol. NH₃ / anschliessendes Behandeln mit wss. Jod-KI-Loesung

With phosphorus; ammonia; hydrogen iodide; acetic acid;

DOI:10.1007/BF03019874

Reference yield:

3,3',5-triiodothyroacetic acid ethyl ester (41628-06-2) → 3,3',5-triiodothyroacetic acid (51-24-1) + [4-(4-Hydroxy-3-iodo-phenoxy)-3-iodo-5-trifluoromethyl-phenyl]-acetic acid + [4-(4-Hydroxy-3-trifluoromethyl-phenoxy)-3,5-diiodo-phenyl]-acetic acid + [4-(4-Hydroxy-3-trifluoromethyl-phenoxy)-3-iodo-5-trifluoromethyl-phenyl]-acetic acid

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; dibromodifluoromethane; copper(I) bromide; cadmium; Multistep reaction. Further byproducts given. Title compound not separated from byproducts;

DOI:10.1248/cpb.44.1273

upstream raw materials:

2-(4-(4-hydroxyphenoxy)-3,5-diiodophenyl)acetic acid

3,3',5-triiodothyroacetic acid ethyl ester

[3,5-diiodo-4-(4-methoxy-phenoxy)-phenyl]-acetic acid ethyl ester

Downstream raw materials:

4-(4-Hydroxy-3-iod-phenoxy)-3,5-diiod-phenethylalkohol

2-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)-N-(phenylsulfonyl)acetamide

2-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)acetamide

2-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)-N-methylacetamide

Refernces