Palmitoyl alanine

Base Information

• Chemical Name: Palmitoyl alanine
• CAS No.: 56255-31-3
• Molecular Formula: C₁₉H₃₇NO₃
• Molecular Weight: 327.508
• UNII: 68HNC9TLVC
• ChEMBL ID: CHEMBL388991
• DSSTox Substance ID: DTXSID80204807
• Metabolomics Workbench ID: 4609
• Nikkaji Number: J740.911G
• Wikidata: Q27264253
• Mol file: 56255-31-3.mol

Synonyms:56255-31-3;Palmitoyl alanine;(S)-2-Palmitamidopropanoic acid;Palmitoyl-L-alanine;N-HEXADECANOYL-ALANINE;N-Hexadecanoyl-L-alanine;N-palmitoyl alanine;Codeage PA;Palmityl-L-alanine;N-Palmitoyl-L-alanine;L-Alanine, N-(1-oxohexadecyl)-;68HNC9TLVC;(2S)-2-(hexadecanoylamino)propanoic acid;UNII-68HNC9TLVC;(S)-2-Palmitamidopropanoicacid;C19H37NO3;palmitoyl L-alanine;N-hexadecanoyl-(l)-alanine;SCHEMBL542879;CHEMBL388991;PALMITOYL ALANINE [INCI];DTXSID80204807;CHEBI:165549;NRBFOSKZAWRBJI-KRWDZBQOSA-N;LMFA08020123;MFCD26793456;AKOS016014303;FD21038;AS-15978;N-Hexadecanoyl-alanine (palmitoyl-Ala-OH);Q27264253

Chemical Property of Palmitoyl alanine

Chemical Property:

• PSA: 66.40000
• LogP: 5.44790
• Storage Temp.: 2-8°C
• XLogP3: 6.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 16
• Exact Mass: 327.27734404
• Heavy Atom Count: 23
• Complexity: 305

Purity/Quality:

98%Min ^*data from raw suppliers

N-Hexadecanoyl-alanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)NC(C)C(=O)O
• Isomeric SMILES: CCCCCCCCCCCCCCCC(=O)N[C@@H](C)C(=O)O
• Uses: suzuki reaction

Technology Process of Palmitoyl alanine

There total 9 articles about Palmitoyl alanine 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: 94.0%

N-hexadecanoyl-L-alanine methyl ester (81912-48-3) → N-n-hexadecanoyl (L)-alanine (56255-31-3,58725-45-4)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; water; at 0 ℃; for 2h;

DOI:10.1016/j.tet.2007.05.028

Reference yield:

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3,136132-75-7) + n-hexadecanoyl chloride (112-67-4) → N-n-hexadecanoyl (L)-alanine (56255-31-3,58725-45-4)

Guidance literature:

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; 6-chloro-1-hydroxybenzotriazole; In N,N-dimethyl-formamide;

With piperidine; In N,N-dimethyl-formamide; for 0.216667h;

n-hexadecanoyl chloride; Further stages;

Reference yield:

n-hexadecanoyl chloride (112-67-4) → N-n-hexadecanoyl (L)-alanine (56255-31-3,58725-45-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / KHCO₃; triethylamine / H₂O; CHCl₃ / 5 h / 0 °C

2: 94 percent / NaOH / methanol; tetrahydrofuran; H₂O / 2 h / 0 °C

With sodium hydroxide; potassium hydrogencarbonate; triethylamine; In tetrahydrofuran; methanol; chloroform; water;

DOI:10.1016/j.tet.2007.05.028

upstream raw materials:

D-Alanine

n-hexadecanoyl chloride

palmitic acid N-succinimide ester

L-alanin

Downstream raw materials:

C₂₈H₄₆N₂O₄

Refernces

• 1、 -. "HUMAN MICROBIOTA DERIVED N-ACYL AMIDES FOR THE TREATMENT OF HUMAN DISEASE". Page/Page column 87-88. . Retrieved 2019/01/17.
• 2、 Nakanishi, Kazuma,Tomita, Masahiro,Kato, Katsuya. "Improvement in the catalytic activity of cytochrome c by immobilisation on a novel mesoporous silica sheet". . p. 4732 - 4735. Retrieved 2014/01/17.