O-(4-Hydroxy-3,5-diiodophenyl)-L-tyrosine

Base Information

• Chemical Name: O-(4-Hydroxy-3,5-diiodophenyl)-L-tyrosine
• CAS No.: 4192-14-7
• Molecular Formula: C15H13I2NO4
• Molecular Weight: 525.082
• Hs Code.: 2922509090
• European Community (EC) Number: 224-071-4
• DSSTox Substance ID: DTXSID80962051
• Nikkaji Number: J224.986C
• Wikidata: Q76390051
• Mol file: 4192-14-7.mol

Synonyms:3',5'-diiodo-L-thyronine;3',5'-diiodothyronine;3',5'-diiodothyronine, (L)-isomer;3',5'-T2

Chemical Property of O-(4-Hydroxy-3,5-diiodophenyl)-L-tyrosine

Chemical Property:

• Vapor Pressure: 1.07E-10mmHg at 25°C
• Melting Point: 206 °C (decomp)
• Boiling Point: 497°C at 760 mmHg
• PKA: 2.21±0.10(Predicted)
• Flash Point: 254.4°C
• PSA: 92.78000
• Density: 2.095g/cm³
• LogP: 4.04840
• 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: 365

Purity/Quality:

99% ^*data from raw suppliers

3’,5’-Diiodo-L-thyronine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=CC=C1CC(C(=O)O)N)OC2=CC(=C(C(=C2)I)O)I
• Isomeric SMILES: C1=CC(=CC=C1C[C@@H](C(=O)O)N)OC2=CC(=C(C(=C2)I)O)I
• Uses: 3’,5’-Diiodo-L-thyronine is a thyroid hormone that has been shown to increase malic enzyme activity, and the activity of glucose-6-phosphate dehydrogenase in teleost Anabas testudineus. Thus, showing short term effect on lipid metabolism.

Technology Process of O-(4-Hydroxy-3,5-diiodophenyl)-L-tyrosine

There total 6 articles about O-(4-Hydroxy-3,5-diiodophenyl)-L-tyrosine 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-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

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) + 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) → 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

upstream raw materials:

L-thyroxine

L-3,3',5'-triiodothyronine

Downstream raw materials:

L-3,3',5'-triiodothyronine

Refernces