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

Base Information

• Chemical Name: (2S)-2-azaniumyl-3-(4-hydroxy-3,5-diiodophenyl)propanoate
• CAS No.: 300-39-0
• Molecular Formula: C9H9I2NO3
• Molecular Weight: 432.984
• Hs Code.: 29225090
• Mol file: 300-39-0.mol

Synonyms:(2S)-2-azaniumyl-3-(4-hydroxy-3,5-diiodophenyl)propanoate

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

Chemical Property:

• Appearance/Colour: white to beige powder
• Vapor Pressure: 1.78E-07mmHg at 25°C
• Melting Point: 200°C (dec.)(lit.)
• Refractive Index: 1.2 ° (C=5, 1mol/L HCl)
• Boiling Point: 410.5 °C at 760 mmHg
• PKA: 2.12(at 25℃)
• Flash Point: 202.1 °C
• PSA: 102.01000
• Density: 2.405 g/cm³
• LogP: 2.12750
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: Aqueous Acid (Slightly), DMSO (Slightly)
• Water Solubility.: slightly soluble
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 432.86719
• Heavy Atom Count: 15
• Complexity: 222

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): R36/37/38:
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36/37-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(C=C(C(=C1I)O)I)CC(C(=O)[O-])[NH3+]
• Isomeric SMILES: C1=C(C=C(C(=C1I)O)I)C[C@@H](C(=O)[O-])[NH3+]
• Description: Diiodotyrosine does not possess pronounced hormonal activity. However, it stops production of thyrotropic hormone by the anterior lobe of the hypophysis, which activates thyroid gland activity.
• Uses: It is used for hyperthyroid forms of endemic and sporadic goiters, diffuse, toxic goiters, and other illnesses accompanied by thyrotoxicity. 3,5-Diiodo-L-tyrosine is a reactant used in the synthesis of fluorescent unnatural amino acids bearing stilbene or vinylene backbones. Also used in the discovery of potent heterodimeric antagonists of inhibitor of Apoptosis proteins with prolonged anti-tumor activity.

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

There total 5 articles about (2S)-2-azaniumyl-3-(4-hydroxy-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: 84.63%

L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) → 3,5-diiodo-l-tyrosine (300-39-0)

Guidance literature:

With hydrogen iodide; acetic acid; In dimethyl sulfoxide; at 65 ℃; for 0.025h;

DOI:10.1039/c8nj04385j

Reference yield: 32.6%

L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) → 3,5-diiodo-l-tyrosine (300-39-0) + 3-Iodo-L-tyrosine (70-78-0)

Guidance literature:

With chloroamine-T; sodium iodide; In water; at 20 ℃; for 0.00277778h; Product distribution; other reaction time, pregenerated iodine, reaction in the presence of tryptophan and Nⁱⁿ-formyl-tryptophan;

Reference yield:

3-Iodo-L-tyrosine (70-78-0) → 3,5-diiodo-l-tyrosine (300-39-0)

Guidance literature:

With iodine; In water; at 22 ℃; for 0.0833333h; potassim iodide/chloramine T in phosphate buffer instead of iodine; tritium isotope effect;

upstream raw materials:

L-tyrosine

3-Iodo-L-tyrosine

ammonia

iodine

Downstream raw materials:

3,5-diiodo-L-tyrosine ethyl ester

L-thyroxine

N-acetyl-3,5-diiodo-L-tyrosine

3.5-diiodo-N.O-diacetyl-L-tyrosine

Refernces

• 1、 Puratchikody, Ayarivan,Umamaheswari, Appavoo,Irfan, Navabshan,Sinha, Shweta,Manju,Ramanan, Meera,Ramamoorthy, Gayathri,Doble, Mukesh. "A novel class of tyrosine derivatives as dual 5-LOX and COX-2/mPGES1 inhibitors with PGE2 mediated anticancer properties". supporting information. p. 834 - 846. Retrieved 2019/01/09.
• 2、 Zewail,Shalaby,Megahed. "Solid phase synthesis of I25 labeled insulin fragments. Part III. Synthesis of 125-I-insulin fragment B15-18 Leu-Tyr(I2)-Leu-Val". . p. 639 - 647. Retrieved 2014/04/03.