3,3'-Diiodo-L-thyronine

Base Information

• Chemical Name: 3,3'-Diiodo-L-thyronine
• CAS No.: 4604-41-5
• Molecular Formula: C₁₅H₁₃I₂NO₄
• Molecular Weight: 525.082
• European Community (EC) Number: 225-005-7
• UNII: 3L9U2Z4602
• DSSTox Substance ID: DTXSID80196697
• Nikkaji Number: J297.843A
• Wikipedia: 3,3'-Diiodothyronine
• Wikidata: Q27104556
• Metabolomics Workbench ID: 52422
• ChEMBL ID: CHEMBL1236140
• Mol file: 4604-41-5.mol

Synonyms:3,3'-diiodothyronine;3,3'-diiodothyronine, (DL)-isomer;3,3'-diiodothyronine, (L)-isomer;3,3'-diiodothyronine, (L)-isomer, 125I-labeled;3,3'-T2

Chemical Property of 3,3'-Diiodo-L-thyronine

Chemical Property:

• Vapor Pressure: 1.14E-11mmHg at 25°C
• Melting Point: 178-180oC
• Refractive Index: 1.726
• Boiling Point: 520.7 °C at 760 mmHg
• PKA: 2.17±0.20(Predicted)
• Flash Point: 268.7 °C
• PSA: 92.78000
• Density: 2.095 g/cm³
• LogP: 4.04840
• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Aqueous Base (Slightly)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 524.89340
• Heavy Atom Count: 22
• Complexity: 385

Purity/Quality:

99% ^*data from raw suppliers

3,3’-Diiodo-L-thyronine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1CC(C(=O)O)N)I)OC2=CC(=C(C=C2)O)I
• Isomeric SMILES: C1=CC(=C(C=C1C[C@@H](C(=O)O)N)I)OC2=CC(=C(C=C2)O)I
• Description: 3,3''-Diiodo-L-thyronine is a metabolite of thyroid hormone that is also known as T2 or 3,3’-T2. It is derived enzymatically from triiodothyronine isoforms T3 and reverse T3. T2 and its analog 3,5-T2 stimulate the activity of cytochrome c oxidase by blocking inhibition by ATP.
• Uses: Of interest for the early detection and treatment of congenital or drug-induced hypothyroidism in the developing human fetus Of interest for the early detection and treatment of congenital or drug-induced hypothyroidism in the developing human fetus.

Technology Process of 3,3'-Diiodo-L-thyronine

There total 15 articles about 3,3'-Diiodo-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:

triiodothyronine (6893-02-3,15785-49-6,7013-53-8) → L-3,3'-Diiodothyronine (70-40-6,58342-32-8,4604-41-5)

Guidance literature:

With Naphthalene-1,8-diselenol; D,L-dithiothreitol; at 37 ℃; pH=7.5; pH-value; Concentration; Time; Reagent/catalyst; regioselective reaction; Kinetics; aq. phosphate buffer;

DOI:10.1021/ja201657s

Reference yield:

triiodothyronine (6893-02-3,15785-49-6,7013-53-8) → 3'-Iodothyronine (4732-82-5) + 3-Monoiodothyronine (10468-90-3) + L-3,3'-Diiodothyronine (70-40-6,58342-32-8,4604-41-5) + 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-3,3',5'-triiodothyronine (5817-39-0) → 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)

Guidance literature:

With sodium tetrahydroborate; C₁₀H₈Te₂; D,L-dithiothreitol; In aq. phosphate buffer; at 37 ℃; for 0.5h; pH=7.5; regioselective reaction;

DOI:10.1002/anie.201502762

upstream raw materials:

3-Monoiodothyronine

N-acetyl-3-iodo-L-tyrosine

(S)-2-Acetylamino-3-[3-iodo-4-(4-methoxy-phenoxy)-phenyl]-propionamide

N-Acetyl-3-iodo-L-tyrosinamid

Downstream raw materials:

3'-Iodothyronine

3-Monoiodothyronine

O-(4-hydroxyphenyl)-3,5-diiodo-L-tyrosine

3,3'-diiodo-L-thyronine sulfate

Refernces

• 1、 Mondal, Santanu,Mugesh, Govindasamy. "Biomimetic deiodination of thyroid hormones and iodothyronamines-a structure-activity relationship study". supporting information. p. 9490 - 9500. Retrieved 2016/10/22.
• 2、 Mondal, Santanu,Mugesh, Govindasamy. "Regioselective deiodination of iodothyronamines, endogenous thyroid hormone derivatives, by deiodinase mimics". supporting information. p. 11120 - 11128,9. Retrieved 2014/11/27.