Argireline

Base Information

• Chemical Name: Argireline
• CAS No.: 616204-22-9
• Molecular Formula: C₃₄H₆₀N₁₄O₁₂S
• Molecular Weight: 889.003
• European Community (EC) Number: 801-648-4
• Nikkaji Number: J2.053.030H
• Wikipedia: Acetyl_hexapeptide-3
• Mol file: 616204-22-9.mol

Synonyms:Ac-EEMQRR-NH2;acetyl hexapeptide-8;acetyl-glutamyl-glutamyl-methionyl-glutaminyl-arginyl-argininamide;argireline

Chemical Property of Argireline

Chemical Property:

• Appearance/Colour: white powder
• Refractive Index: 1.66
• PKA: 4.43±0.10(Predicted)
• PSA: 484.48000
• Density: 1.54 g/cm³
• LogP: 0.80300
• Storage Temp.: ?20°C
• Solubility.: water soluble
• XLogP3: -6.3
• Hydrogen Bond Donor Count: 14
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 32
• Exact Mass: 888.42358458
• Heavy Atom Count: 61
• Complexity: 1610

Purity/Quality:

97% ^*data from raw suppliers

Ac-EEMQRR-NH2 trifluoroacetate salt ≥95% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(CCC(=O)O)C(=O)NC(CCC(=O)O)C(=O)NC(CCSC)C(=O)NC(CCC(=O)N)C(=O)NC(CCCN=C(N)N)C(=O)NC(CCCN=C(N)N)C(=O)N
• Isomeric SMILES: CC(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N
• Recent ClinicalTrials: Argireline in Treatment of Periorbital Wrinkles
• Description: Argireline is made up of chains of amino acids. Such chains can affect how our cells work, e.g. relaxing our face muscles. It is derived from the peptide Acetyl hexapeptide-3, a substrate of Botulinum toxin, or more commonly known as Botox.
• Uses: Argireline is an anti-wrinkle peptide. Synthetically produced and considered to be highly effective, clinical studies indicate it can reduce the depth of existing wrinkles. May be incorporated into products marketed as having a topical-BoToX. or “wrinkle-erasing” effect.

Technology Process of Argireline

There total 2 articles about Argireline 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: 42.16%

C20H18N2O11S2(2-)*2Na(1+) + C24H25NO12S2(2-)*2Na(1+) + C20H19NO10S3(2-)*2Na(1+) + C21H22N4O10S2(2-)*2Na(1+) → Ac-Glu-Glu-Met-Gln-Arg-Arg-NH2 (616204-22-9)

Guidance literature:

C₂₁H₂₂N₄O₁₀S₂^(2-)*2Na⁽¹⁺⁾; With sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; ethyl cyanoglyoxylate-2-oxime; In water; at 20 ℃; for 0.75h;

With sodium hydroxide; In water; for 0.0833333h;

C₂₀H₁₈N₂O₁₁S₂^(2-)*2Na⁽¹⁺⁾; C₂₄H₂₅NO₁₂S₂^(2-)*2Na⁽¹⁺⁾; C₂₀H₁₉NO₁₀S₃^(2-)*2Na⁽¹⁺⁾; C₂₁H₂₂N₄O₁₀S₂^(2-)*2Na⁽¹⁺⁾; acetyl source; Further stages;

DOI:10.1002/anie.202003676

Reference yield:

Fmoc-Glu(OtBu)-OH (71989-18-9) + acetic anhydride (108-24-7) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine (71989-28-1) + Fmoc-L-Gln(Trt)-OH (132327-80-1,200623-62-7) + Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine (187618-60-6) → Ac-Glu-Glu-Met-Gln-Arg-Arg-NH2 (616204-22-9)

Guidance literature:

Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine; With benzotriazol-1-ol; diisopropyl-carbodiimide; In N,N-dimethyl-formamide; at 25 ℃; for 1h;

With piperidine; In N,N-dimethyl-formamide; at 25 ℃;

Fmoc-Glu(OtBu)-OH; acetic anhydride; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine; Fmoc-L-Gln(Trt)-OH; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine; Further stages;

upstream raw materials:

Fmoc-Glu(OtBu)-OH

acetic anhydride

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine

Fmoc-L-Gln(Trt)-OH

Refernces

• 1、 -. "COMPOUNDS USEFUL FOR THE TREATMENT AND/OR CARE OF THE SKIN, HAIR, NAILS AND/OR MUCOUS MEMBRANES". Paragraph 0167; 0178-0182; 0185-0188. . Retrieved 2018/06/21.