3,3',5'-Triiodo-L-thyronine

Base Information

• Chemical Name: 3,3',5'-Triiodo-L-thyronine
• CAS No.: 5817-39-0
• Deprecated CAS: 2820-50-0
• Molecular Formula: C15H12I3NO4
• Molecular Weight: 650.978
• Hs Code.: 29379000
• European Community (EC) Number: 621-265-4
• UNII: 8NZ4Y08T96
• DSSTox Substance ID: DTXSID3046908
• Nikkaji Number: J402.028F
• Wikipedia: Reverse_triiodothyronine
• Wikidata: Q60998609
• Metabolomics Workbench ID: 53573
• ChEMBL ID: CHEMBL1743304
• Mol file: 5817-39-0.mol

Synonyms:3,3',5'-Triiodothyronine;3,3,5 Triiodothyronine;3,3,5-Triiodothyronine;Reverse T3 Thyroid hormone;Reverse Triiodothyronine;Triiodothyronine, Reverse

Chemical Property of 3,3',5'-Triiodo-L-thyronine

Chemical Property:

• Appearance/Colour: powder
• Melting Point: 234-238 °C(lit.)
• Boiling Point: 534.6 °C at 760 mmHg
• PKA: 2.17±0.20(Predicted)
• Flash Point: 277.1 °C
• PSA: 92.78000
• Density: 2.387 g/cm³
• LogP: 4.65300
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 650.7901
• Heavy Atom Count: 23
• Complexity: 402

Purity/Quality:

99%, ^*data from raw suppliers

Triiodothyronine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T,F
• Statements: 36/37/38-20/21/22-39/23/24/25-23/24/25-11
• Safety Statements: 36-45-36/37-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C=C1CC(C(=O)O)N)I)OC2=CC(=C(C(=C2)I)O)I
• Isomeric SMILES: C1=CC(=C(C=C1C[C@@H](C(=O)O)N)I)OC2=CC(=C(C(=C2)I)O)I
• Description: Either a derivative or precursor of thyroxine. Triiodothyronine increases themetabolic rate and oxygen consumption of animal tissues. Used in biochemical research, medicine (metabolic insufficiency).
• Uses: One of the hormones produced by the thyroid gland that is involved in the maintenance of metabolic homeostasis. Also produced in peripheral tissues as the active metabolite of Thyroxine.

Technology Process of 3,3',5'-Triiodo-L-thyronine

There total 11 articles about 3,3',5'-Triiodo-L-thyronine 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:

L-thyroxine (51-48-9,24486-40-6) → 3'-Iodothyronine (4732-82-5) + 3-Monoiodothyronine (10468-90-3) + L-3,3'-Diiodothyronine (70-40-6,58342-32-8,4604-41-5) + 3',5'-Diiodothyronine (4192-14-7) + L-3,3',5'-triiodothyronine (5817-39-0) + O-(4-hydroxyphenyl)-3,5-diiodo-L-tyrosine (1596-67-4)

Guidance literature:

With sodium tetrahydroborate; C₁₀H₈STe; D,L-dithiothreitol; In aq. phosphate buffer; at 37 ℃; for 0.5h; pH=7.5; Reagent/catalyst; regioselective reaction;

DOI:10.1002/anie.201502762

Reference yield:

L-thyroxine (51-48-9,24486-40-6) → L-3,3',5'-triiodothyronine (5817-39-0)

Guidance literature:

With diothiothreitol; rat liver microsomal protein 5'-T₄-deiodinase (5'-T₄Dase); In phosphate buffer; at 37 ℃; for 0.5h; pH=7.4; Further Variations:; reaction time; Enzyme kinetics;

DOI:10.1007/s002280050701

Reference yield:

3-Monoiodothyronine (10468-90-3) → L-3,3',5'-triiodothyronine (5817-39-0)

Guidance literature:

With ammonium hydroxide; iodine;

DOI:10.1021/jm00230a018

upstream raw materials:

3',5'-Diiodothyronine

3-Monoiodothyronine

L-thyroxine

N-acetyl-3-iodo-L-tyrosine

Downstream raw materials:

3'-Iodothyronine

3-Monoiodothyronine

L-3,3'-Diiodothyronine

3',5'-Diiodothyronine

Refernces

• 1、 Raja, Karuppusamy,Mugesh, Govindasamy. "Remarkable Effect of Chalcogen Substitution on an Enzyme Mimetic for Deiodination of Thyroid Hormones". supporting information. p. 7674 - 7678. Retrieved 2015/06/25.
• 2、 Manna, Debasish,Mugesh, Govindasamy. "Regioselective deiodination of thyroxine by iodothyronine deiodinase mimics: An unusual mechanistic pathway involving cooperative chalcogen and halogen bonding". supporting information; experimental part. p. 4269 - 4279. Retrieved 2012/04/10.