N-Myristoyl-L-serine

Base Information

• Chemical Name: N-Myristoyl-L-serine
• CAS No.: 21394-57-0
• Molecular Formula: C₁₇H₃₃NO₄
• Molecular Weight: 315.453
• European Community (EC) Number: 244-363-5
• DSSTox Substance ID: DTXSID00943943
• Mol file: 21394-57-0.mol

Synonyms:N-Myristoyl-L-serine;N-Myristoyl serine;3-hydroxy-2-(tetradecanoylamino)propanoic acid;N-Tetradecanoylserine;EINECS 244-363-5;(2S)-3-hydroxy-2-(tetradecanoylamino)propanoic acid;SCHEMBL4743339;DTXSID00943943;N-(1-Hydroxytetradecylidene)serine

Chemical Property of N-Myristoyl-L-serine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.481
• Boiling Point: 519.793 °C at 760 mmHg
• Flash Point: 268.162 °C
• PSA: 86.63000
• Density: 1.025 g/cm³
• LogP: 3.64010
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 15
• Exact Mass: 315.24095853
• Heavy Atom Count: 22
• Complexity: 294

Purity/Quality:

98%min ^*data from raw suppliers

N-MYRISTOYL-L-SERINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCC(=O)NC(CO)C(=O)O

Technology Process of N-Myristoyl-L-serine

There total 4 articles about N-Myristoyl-L-serine 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: 45.0%

serin (302-84-1,83245-15-2) + tetradecanoyl chloride (112-64-1) → DL-3-Hydroxy-2-tetradecanoylamino-propionsaeure (21394-65-0,21394-57-0)

Guidance literature:

With sodium hydroxide; In acetone;

DOI:10.1021/jf00052a004

Reference yield:

L-serin (56-45-1,83245-15-2) + tetradecanoyl chloride (112-64-1) → N-myristoyl serine (21394-57-0)

Guidance literature:

With sodium hydroxide;

Reference yield:

n-tetradecanoic acid (544-63-8) → N-myristoyl serine (21394-57-0)

Guidance literature:

Multi-step reaction with 2 steps

1: phosphorus trichloride / 5 h / 40 - 100 °C

2: sodium hydrogencarbonate / water; tetrahydrofuran / 20 h

With sodium hydrogencarbonate; phosphorus trichloride; In tetrahydrofuran; water; 2: |Schotten-Baumann Reaction;

DOI:10.1007/s11743-012-1432-2

upstream raw materials:

serin

tetradecanoyl chloride

L-serin

n-tetradecanoic acid

Refernces

• 1、 Xia, Jiding,Xia, Yongmei,Nnanna, Ifendu A.. "Structure-Function Relationship of Acyl Amino Acid Surfactants: Surface Activity and Antimicrobial Properties". . p. 867 - 871. Retrieved 2007/10/02.
• 2、 Sciortino,Du Ban. "Antiviral potentials. 8. Highter N-acyl derivatives of various amino acids". . p. 498 - 505. Retrieved 2007/10/06.