N-(octadecanoyl)-4R-hydroxysphinganine

Base Information

• Chemical Name: N-(octadecanoyl)-4R-hydroxysphinganine
• CAS No.: 34354-88-6
• Molecular Formula: C36H73NO4
• Molecular Weight: 583.96900
• Hs Code.: 2924199090
• European Community (EC) Number: 812-962-6
• DSSTox Substance ID: DTXSID80963881,DTXSID901335580
• Nikkaji Number: J939.982H
• Wikidata: Q27135594
• Metabolomics Workbench ID: 30692
• Mol file: 34354-88-6.mol

Synonyms:N-stearoylphytosphingosine

Chemical Property of N-(octadecanoyl)-4R-hydroxysphinganine

Chemical Property:

• Vapor Pressure: 0Pa at 25℃
• Melting Point: 122-124°C
• Boiling Point: 718℃ at 10hPa
• PSA: 93.28000
• Density: 0.994-1.014 at 20℃
• LogP: 10.37830
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform : Methanol = 3 : 1 (Slightly), Pyridine (Slightly, Heated, Sonicated)
• XLogP3: 13.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 33
• Exact Mass: 583.55395981
• Heavy Atom Count: 41
• Complexity: 530

Purity/Quality:

99%, ^*data from raw suppliers

N-Stearoyl Phytosphingosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCCCC(=O)NC(CO)C(C(CCCCCCCCCCCCCC)O)O
• Isomeric SMILES: CCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@@H]([C@@H](CCCCCCCCCCCCCC)O)O
• Uses: An intercellular lipid that benefits skin hydration and protects against SLS irritation.

Technology Process of N-(octadecanoyl)-4R-hydroxysphinganine

There total 8 articles about N-(octadecanoyl)-4R-hydroxysphinganine 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: 96.0%

D-ribo-phytosphingosine (554-62-1) + stearic acid (57-11-4) → (2S,3S,4R)-2-(N-stearoylamino)octadecane-1,3,4-triol (34354-88-6)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;

DOI:10.1055/s-2006-949649

Reference yield: 87.5%

D-ribo-phytosphingosine (554-62-1) + stearic acid ethyl ester (111-61-5) → (2S,3S,4R)-2-(N-stearoylamino)octadecane-1,3,4-triol (34354-88-6)

Guidance literature:

With sodium ethanolate; In ethanol; at 55 ℃; Temperature;

Reference yield:

glycerol tristearate (555-43-1) + D-ribo-phytosphingosine (554-62-1) → (2S,3S,4R)-2-(N-stearoylamino)octadecane-1,3,4-triol (34354-88-6)

Guidance literature:

Novozym 435; In 1,4-dioxane; at 80 ℃; under 760.051 Torr; Enzymatic reaction;

upstream raw materials:

D-ribo-phytosphingosine

Stearoyl chloride

stearic acid

glycerol tristearate

Downstream raw materials:

(2S,3S,4R)-1-O-tert-butyldiphenylsilyl-2-octadecanoylamino-octadecane