(2S)-2-azaniumyl-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoate

Base Information

• Chemical Name: (2S)-2-azaniumyl-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoate
• CAS No.: 6893-02-3
• Molecular Formula: C15H12I3NO4
• Molecular Weight: 650.978
• Hs Code.: 29225090
• Mol file: 6893-02-3.mol

Synonyms:L-triiodothyronine;(2S)-2-azaniumyl-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoate;CHEBI:533015;3,3',5-triiodo-L-thyronine zwitterion;4-(3-iodo-4-hydroxy-phenoxy)-3,5-diiodophenylalanine;(S)-2-Amino-3-[4-(4-hydroxy-3-iodo-phenoxy)-3,5-diiodo-phenyl]-propionic acid

Chemical Property of (2S)-2-azaniumyl-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoate

Chemical Property:

• Appearance/Colour: Off-white solid
• Melting Point: 234-238 °C(lit.)
• Boiling Point: 563.527 °C at 760 mmHg
• PKA: pKa 8.5 (Uncertain);8.4 (Uncertain);8.45 (Uncertain)
• Flash Point: 294.611 °C
• PSA: 92.78000
• Density: 2.387 g/cm³
• LogP: 4.65300
• Storage Temp.: −20°C
• Sensitive.: Light Sensitive
• Solubility.: DMSO (Slightly), Methanol (Very Slightly)
• Water Solubility.: Insoluble in water, ethanol and propylene glycol. Soluble in dilute alkalies.
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 650.7901
• Heavy Atom Count: 23
• Complexity: 397

Purity/Quality:

99%, ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xn,Xi,T,F
• Statements: 20/21/22-36/37/38-39/23/24/25-23/24/25-11
• Safety Statements: 36-26-36/37/39-45-36/37-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1OC2=C(C=C(C=C2I)CC(C(=O)[O-])[NH3+])I)I)O
• Isomeric SMILES: C1=CC(=C(C=C1OC2=C(C=C(C=C2I)C[C@@H](C(=O)[O-])[NH3+])I)I)O
• Description: Crystalline T3 (liothyronine sodium, Cytomel) has a rapid onset and short duration of action. It is the therapy of choice when it is desirable to have rapid onset or cessation of activity, such as in patients with heart disease.
• Uses: 3,3’,5-Triiodo-L-thyronine (Levothyroxine EP Impurity A) is 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. T3 or 3,3',5-Triiodo-L-thyronine is a thyroid hormone involved with many physiological processes in the human body including growth and development, metabolism, body temperature and heart rate. Free and total T3 serum levels are measured by LC-MS/MS for determination of hyperthyroidism caused by excess T3. This Certified Spiking Solution? is suitable for use as a starting material in preparation of linearity standards, calibrators, and controls for thyroid hormone testing methods by LC-MS/MS.

Technology Process of (2S)-2-azaniumyl-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoate

There total 7 articles about (2S)-2-azaniumyl-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoate 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: 70.0%

3,5-diiodo-l-tyrosine (300-39-0) + 5-Iodo-1-oxa-spiro[2.5]octa-4,7-dien-6-one → triiodothyronine (6893-02-3,15785-49-6,7013-53-8)

Guidance literature:

In N,N-dimethyl-formamide; at 24 ℃; for 16h; 0.2 M borate buffer, pH 8.0 (add. of 0.1 M NaOH);

DOI:10.1016/S0040-4039(97)01665-1

Reference yield:

liothyronine sodium (55-06-1) → triiodothyronine (6893-02-3,15785-49-6,7013-53-8)

Guidance literature:

With acetic acid; In water; Large scale;

Reference yield:

3,5-diiodo-L-thyronine (1041-01-6,534-51-0,5563-89-3,299-82-1) → triiodothyronine (6893-02-3,15785-49-6,7013-53-8)

Guidance literature:

With sodium hydroxide; iodine;

upstream raw materials:

3,5-diiodo-L-thyronine

3,5-diiodo-l-tyrosine

thyroxine

liothyronine sodium

Downstream raw materials:

C₁₃H₁₅NSSe

L-3,3'-Diiodothyronine

naphtho<1,8-cd>thiaselenole

1,8-naphthalenedisulfide

Refernces

• 1、 -. "IMMUNOTHERAPY AGAINST SEVERAL TUMORS, SUCH AS LUNG CANCER, INCLUDING NSCLC". . . Retrieved 2016/07/05.
• 2、 Lattuada, Luciano,Argese, Maria,Boi, Valeria,Galimberti, Laura,Gazzetto, Sonia. "Process development and scale-up of T3-Sulfate, a new prodrug alternative to the conventional hormone therapy of hypothyroidism". . p. 1175 - 1180. Retrieved 2014/12/10.