Undecylenoyl phenylalanine

Base Information

• Chemical Name: Undecylenoyl phenylalanine
• CAS No.: 175357-18-3
• Molecular Formula: C₂₀H₂₉NO₃
• Molecular Weight: 331.455
• European Community (EC) Number: 446-800-7,806-191-4
• UNII: 271P08C6OD
• DSSTox Substance ID: DTXSID701018253
• Nikkaji Number: J2.930.011I
• Wikidata: Q27254148
• Mol file: 175357-18-3.mol

Synonyms:undecylenoyl phenylalanine;175357-18-3;Sepiwhite msh;Sepiwhite msh QD;undecylenoylphenylalanine;L-Phenylalanine, N-(1-oxo-10-undecenyl)-;N-Undecenoyl-L-phenylalanine;271P08C6OD;Undecylenoyl phenylalanine [INCI];(2S)-3-phenyl-2-(undec-10-enoylamino)propanoic Acid;UNII-271P08C6OD;L-Phenylalanine, N-(1-oxo-10-undecen-1-yl)-;(2S)-3-phenyl-2-[[(E)-undec-2-enoyl]amino]propanoic Acid;UNDECYLENOYL PHENYLALANINE (SEPIWHITE);(S)-3-Phenyl-2-(undec-10-enamido)propanoic acid;N-(1-oxo-10-undecen-1-yl)-L-Phenylalanine;N-(10-Undecenoyl)-Phe-OH;SCHEMBL144776;DTXSID701018253;AMY42000;BS-51480;F71335;Q27254148

Chemical Property of Undecylenoyl phenylalanine

Chemical Property:

• Vapor Pressure: 0-0Pa at 25-60℃
• Melting Point: 109-112 °C
• Boiling Point: 540.0±50.0 °C(Predicted)
• PKA: 3.63±0.10(Predicted)
• PSA: 66.40000
• Density: 1.047±0.06 g/cm3(Predicted)
• LogP: 4.49620
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 13
• Exact Mass: 331.21474379
• Heavy Atom Count: 24
• Complexity: 375

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCCCCCCCCC(=O)NC(CC1=CC=CC=C1)C(=O)O
• Isomeric SMILES: C=CCCCCCCCCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O
• Description: Undecylenoyl Phenylalanine is a chemical compound—a substituted amino acid derivative—that is used in skin conditioning agents in different brands of whitening creams and other skin care topical products. The compound helps regulate skin pigmentation, thereby, improving skin tone and its fairness.Undecylenoyl phenylalanine is a possible antagonist of alpha-melanocyte-stimulatinghormone. It inhibits melanotropin, a melanin stimulator found in the skin. Melanotropin controls tyrosinase activity (tyrosinase being an essential enzyme in the production of melanin), melanin (eumalanin) synthesis and melanosome; therefore, by preventing the production of melanotropin, the pigmentation process is reduced or halted.
• Uses: Undecylenoyl phenylalanine is a novel skin-lightening agent, probably acting as α-melanocyte-stimulating hormone (α-MSH) and beta-adrenergic receptor (β-ADR) antagonist.
• Clinical Use: A study was done to evaluate the efficacy and safety of a preparation containing undecylenoyl phenylalanine 2% in the topical treatment of solar lentigines. In total, 36 patients with solar lentigines of the hands were randomly assigned to apply the active preparation on one side and the vehicle alone on the other side, twice daily for 12 weeks. Undecylenoyl phenylalanine 2% is a novel depigmenting agent, which possibly acts as an alpha-melanocyte-stimulating hormone antagonist, thus inhibiting melaninogenesis. It achieved a significant lightening of the lesions with minimal side-effects. Most patients were satisfied with the improvement.

Technology Process of Undecylenoyl phenylalanine

There total 4 articles about Undecylenoyl phenylalanine 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:

10-undecenoic acid (112-38-9) + L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → N-Undecylenoylphenylalanine (175357-18-3)

Guidance literature:

With aminoacylases from Streptomyces ambofaciens; cobalt(II) chloride; In aq. buffer; at 45 ℃; pH=7 - 8; Enzymatic reaction;

DOI:10.1016/j.procbio.2020.09.009

Reference yield:

10-undecenoic acid (112-38-9) → N-Undecylenoylphenylalanine (175357-18-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / thionyl chloride / 2 h / Heating

2: 1.) trimethylsilyl chloride, pyridine / 1.) CH₂Cl₂, 2.) CH₂Cl₂

With pyridine; chloro-trimethyl-silane; thionyl chloride;

DOI:10.1021/jm950358j

Reference yield:

undec-10-enoyl chloride (38460-95-6) + L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → N-Undecylenoylphenylalanine (175357-18-3)

Guidance literature:

With pyridine; chloro-trimethyl-silane; Yield given. Multistep reaction; 1.) CH₂Cl₂, 2.) CH₂Cl₂;

DOI:10.1021/jm950358j

upstream raw materials:

undec-10-enoyl chloride

L-phenylalanine

10-undecenoic acid

Refernces

• 1、 Leydet,El Hachemi,Boyer,Lamaty,Roque,Schols,Snoeck,Andrei,Ikeda,Neyts,Reymen,Este,Witvrouw,De Clercq. "Polyanion inhibitors of human immunodeficiency virus and other viruses. Part 2. Polymerized anionic surfactants derived from amino acids and dipeptides". . p. 1626 - 1634. Retrieved 1996.