N-docosanoylsphingosine

Base Information

• Chemical Name: N-docosanoylsphingosine
• CAS No.: 27888-44-4
• Molecular Formula: C40H79NO3
• Molecular Weight: 622.072
• Nikkaji Number: J856.871E
• Wikidata: Q27140219
• Metabolomics Workbench ID: 30568
• Mol file: 27888-44-4.mol

Synonyms:C22-ceramide;N-docosanoyl-16-methylheptadecasphing-4-enine

Chemical Property of N-docosanoylsphingosine

Chemical Property:

• Boiling Point: 731.8±60.0 °C(Predicted)
• PKA: 13.54±0.20(Predicted)
• PSA: 69.56000
• Density: 0.909±0.06 g/cm3(Predicted)
• LogP: 12.29450
• XLogP3: 16.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 36
• Exact Mass: 621.60599538
• Heavy Atom Count: 44
• Complexity: 593

Purity/Quality:

97% ^*data from raw suppliers

C22 Ceramide (d18:1/22:0) ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCCCCCCCC(=O)NC(CO)C(C=CCCCCCCCCCCCCC)O
• Isomeric SMILES: CCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@@H](/C=C/CCCCCCCCCCCCC)O

Technology Process of N-docosanoylsphingosine

There total 2 articles about N-docosanoylsphingosine 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: 68.0%

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4) + n-docosanoic acid (112-85-6) → (2S,3R)-N-(docosanoate)-1,3-dihydroxy-2-amino-octadeca-4-(E)-ene (27888-44-4)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 20 ℃;

Reference yield:

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4) + p-nitrophenyl docosanoate → (2S,3R)-N-(docosanoate)-1,3-dihydroxy-2-amino-octadeca-4-(E)-ene (27888-44-4)

Guidance literature:

With dmap; In tetrahydrofuran; at 40 ℃; for 12h;

DOI:10.1021/jm00012a018

Reference yield:

methanol (67-56-1) + (2S,3R)-N-(docosanoate)-1,3-dihydroxy-2-amino-octadeca-4-(E)-ene (27888-44-4) → behenic acid methyl ester (929-77-1)

Guidance literature:

With sulfuric acid; In water; for 4h; Heating;

upstream raw materials:

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

n-docosanoic acid

Downstream raw materials:

behenic acid methyl ester

Cer (d18:0/22:0)