Melanostatin

Base Information

• Chemical Name: Melanostatin
• CAS No.: 2002-44-0
• Deprecated CAS: 15569-83-2
• Molecular Formula: C13H24N4O3
• Molecular Weight: 284.359
• European Community (EC) Number: 217-902-7
• UNII: 3KY24B4Q62
• DSSTox Substance ID: DTXSID20173841
• Nikkaji Number: J22.676I
• Wikipedia: Melanocyte-inhibiting_factor
• Wikidata: Q6811443
• Metabolomics Workbench ID: 38740
• ChEMBL ID: CHEMBL317488
• Mol file: 2002-44-0.mol

Synonyms:H-Pro-Leu-Gly-NH2;Melanocyte-Stimulating Hormone Release-Inhibiting Factor;Melanocyte-Stimulating Hormone Release-Inhibiting Hormone;Melanostatin;MIF-1;MIF-I;MSH Release-Inhibiting Factor;MSH Release-Inhibiting Hormone;Oxytocin (7-9);Pro-Leu-Gly-NH2;Pro-Leu-Glyamide;Prol Leu Gly NH2;Prol-Leu-Gly-NH2;Prolyl Leucyl Glycinamide;Prolyl-Leucyl-Glycinamide;Prolylleucylglycinamide

Chemical Property of Melanostatin

Chemical Property:

• Vapor Pressure: 1.34E-15mmHg at 25°C
• Melting Point: 122-123 °C(Solv: water (7732-18-5))
• Refractive Index: 1.51
• Boiling Point: 626.2 °C at 760 mmHg
• PKA: 14.10±0.20(Predicted)
• Flash Point: 332.5 °C
• PSA: 113.32000
• Density: 1.147 g/cm³
• LogP: 0.68170
• Storage Temp.: -15°C
• Solubility.: ≥59.1 mg/mL in DMSO; ≥50 mg/mL in EtOH; ≥50 mg/mL in H2O
• Water Solubility.: Soluble in water.
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 284.18484064
• Heavy Atom Count: 20
• Complexity: 371

Purity/Quality:

99% ^*data from raw suppliers

Melanocyte Stimulating Hormone Release Inhibiting Factor ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(C(=O)NCC(=O)N)NC(=O)C1CCCN1
• Isomeric SMILES: CC(C)C[C@@H](C(=O)NCC(=O)N)NC(=O)[C@@H]1CCCN1
• Uses: L-Prolyl-L-leucylglycinamide is shown to be effective in treating human depression with greater efficacy and faster onset of action than traditional anti-depressants.Also, it is used in the synthesis of novel analogs to be tested for their ability to enhance the binding of [3H]-N-propylnorapomorphine to short isoform of human dopamine D2 receptors.

Technology Process of Melanostatin

There total 44 articles about Melanostatin 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: 99.7%

benzoyloxycarbonylprolyl-leucyl-glycine amide (14485-80-4) → melanostatin (2002-44-0)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In methanol;

Reference yield: 92.0%

→ melanostatin (2002-44-0)

Guidance literature:

With p-cresol; hydrogen fluoride; at 0 ℃; for 1h;

DOI:10.1016/S0040-4039(01)81767-6

Reference yield: 90.0%

PChd-L-Pro-L-Leu-Gly-NH2 (74763-82-9) → 2,6-di(t-butyl)-4-phenylphenol (2668-47-5) + melanostatin (2002-44-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 3h;

DOI:10.1002/jlac.198219820608

upstream raw materials:

glycinamide hydrochloride

(2S)-2-{[(2S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carbonyl]amino}-4-methylpentanoic acid

Boc-L-Pro-L-Leu-Gly-NH₂

MOC-Pro-Leu-Gly-NH₂

Downstream raw materials:

1-N-(2-carboxy-phenyl)-carbamoyl-L-prolyl-L-leucyl-glycinamide

Boc-Tan-Cys(PMB)-Pro-Leu-Gly-NH₂

Boc-Can-Cys(PMB)-Pro-Leu-Gly-NH₂

Cys(PMB)-Pro-Leu-Gly-NH₂

Refernces

• 1、 Ivanov, A. K.,Antonov, A. A.,Donetskii, I. A.. "SYNTHESIS OF THE AMIDE OF THE C-TERMINAL TETRAPEPTIDE OF THE SEQUENCE OF OXYTOCIN". . p. 344 - 349. Retrieved 2007/10/02.
• 2、 Khalifa,Jung,Rieker. "Peptide syntheses with the N-PChd protective group. Synthesis of the hydrophobic segment 14-20 L-Ala-Leu-Ile-Leu-Leu-Ala-Gln of human lymphoblastoid interferon". . p. 1068 - 1090. Retrieved 2007/10/02.