O-(4-Hydroxyphenyl)-3-iodo-L-tyrosine

Base Information

• Chemical Name: O-(4-Hydroxyphenyl)-3-iodo-L-tyrosine
• CAS No.: 10468-90-3
• Molecular Formula: C15H14 I N O4
• Molecular Weight: 399.185
• Hs Code.: 2922509090
• European Community (EC) Number: 233-955-9
• DSSTox Substance ID: DTXSID501316158
• Nikkaji Number: J212.408D
• Wikidata: Q76010002
• Mol file: 10468-90-3.mol

Synonyms:3-iodothyronine;3-monoiodothyronine;3-monoiodothyronine, (DL-Tyr)-isomer;3-monoiodothyronine, (L-Tyr)-isomer;3-monoiodothyronine, 125I-labeled, (L-Tyr)-isomer;3-T1

Chemical Property of O-(4-Hydroxyphenyl)-3-iodo-L-tyrosine

Chemical Property:

• Vapor Pressure: 1.81E-11mmHg at 25°C
• Melting Point: 191-193°C
• Boiling Point: 515.9°Cat760mmHg
• PKA: 2.19±0.20(Predicted)
• Flash Point: 265.8°C
• PSA: 92.78000
• Density: 1.746g/cm³
• LogP: 3.44380
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: Aqueous Base (Slightly), DMSO (Very Slightly), Ethanol (Slightly), Methanol (Ver
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 398.99676
• Heavy Atom Count: 21
• Complexity: 347

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Iodo-L-thyronine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1O)OC2=C(C=C(C=C2)CC(C(=O)O)N)I
• Isomeric SMILES: C1=CC(=CC=C1O)OC2=C(C=C(C=C2)C[C@@H](C(=O)O)N)I
• Uses: A metabolite of thyroid hormone. Of interest for the early detection and treatment of congenital or drug-induced hypothyroidism in the developing human fetus A metabolite of thyroid hormone. Of interest for the early detection and treatment of congenital or drug-induced hypothyroidism in the developing human fetus.

Technology Process of O-(4-Hydroxyphenyl)-3-iodo-L-tyrosine

There total 16 articles about O-(4-Hydroxyphenyl)-3-iodo-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:

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

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

upstream raw materials:

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

N-acetyl-3-iodo-L-tyrosine

N-Acetyl-3-iodo-L-tyrosinamid

L-thyroxine

Downstream raw materials:

L-3,3'-Diiodothyronine

L-3,3',5'-triiodothyronine

Refernces

• 1、 Raja, Karuppusamy,Mugesh, Govindasamy. "Remarkable Effect of Chalcogen Substitution on an Enzyme Mimetic for Deiodination of Thyroid Hormones". . p. 7674 - 7678. Retrieved 2015.
• 2、 Block Jr.. "Synthesis of 3 iodo L thyronine and its iodinated derivatives". . p. 1067 - 1069. Retrieved 2007/10/16.