N-(octadecanoyl)-sphinganine

Base Information

• Chemical Name: N-(octadecanoyl)-sphinganine
• CAS No.: 2304-80-5
• Molecular Formula: C₃₆H₇₃NO₃
• Molecular Weight: 567.981
• UNII: 8AD8CNQ956,C04977SRJ5
• DSSTox Substance ID: DTXSID50177594
• Nikkaji Number: J525.221K
• Wikidata: Q27135592
• RXCUI: 1426448
• Metabolomics Workbench ID: 30654
• Mol file: 2304-80-5.mol

Synonyms:C18-(dihydro)ceramide;N-stearoyl-sphinganine;N-stearoylsphinganine

Chemical Property of N-(octadecanoyl)-sphinganine

Chemical Property:

• Vapor Pressure: 2.48E-22mmHg at 25°C
• Melting Point: 104-106°C
• Boiling Point: 694.8°C at 760 mmHg
• PKA: 14.30±0.20(Predicted)
• Flash Point: 374°C
• PSA: 69.56000
• Density: 0.909g/cm³
• LogP: 10.95810
• XLogP3: 14.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 33
• Exact Mass: 567.55904519
• Heavy Atom Count: 40
• Complexity: 498

Purity/Quality:

98%Min ^*data from raw suppliers

C18Dihydroceramide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCCCC(=O)NC(CO)C(CCCCCCCCCCCCCCC)O
• Isomeric SMILES: CCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@@H](CCCCCCCCCCCCCCC)O
• Uses: C18 Dihydroceramide can be used for ceramide composition with repairing function and cosmetic.

Technology Process of N-(octadecanoyl)-sphinganine

There total 6 articles about N-(octadecanoyl)-sphinganine 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: 95.0%

ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate (1018676-90-8) → (2S,3R)-2-octadecanoylaminooctadecane-1,3-diol (21481-56-1,54353-27-4,54353-28-5,96673-02-8,2304-80-5)

Guidance literature:

ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate; With sodium tetrahydroborate; In tetrahydrofuran; at 0 ℃; for 5h;

With calcium chloride; In tetrahydrofuran; for 1h; Product distribution / selectivity;

Reference yield:

(2S,3R)-2-amino-1,3-octadecanediol (764-22-7,2304-75-8,3102-56-5,3102-60-1,6036-76-6,6036-86-8,13552-09-5,15639-50-6,73938-69-9) + Stearoyl chloride (112-76-5) → (2S,3R)-2-octadecanoylaminooctadecane-1,3-diol (21481-56-1,54353-27-4,54353-28-5,96673-02-8,2304-80-5)

Guidance literature:

With pyridine; N,N-dimethyl acetamide;

DOI:10.1021/ja01550a061

Reference yield:

methyl stearate (methyl octadecanoate) + (2S,3R)-2-amino-1,3-octadecanediol (764-22-7,2304-75-8,3102-56-5,3102-60-1,6036-76-6,6036-86-8,13552-09-5,15639-50-6,73938-69-9) → (2S,3R)-2-octadecanoylaminooctadecane-1,3-diol (21481-56-1,54353-27-4,54353-28-5,96673-02-8,2304-80-5)

Guidance literature:

With potassium hydroxide; nitrogen; In butan-1-ol;

upstream raw materials:

(2S,3R)-2-amino-1,3-octadecanediol

Stearoyl chloride

2-aminooctadecan-1,3-diol

ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate

Downstream raw materials:

D-erythro-2-octadecylamino-octadecane-1,3-diol

(2R,3R) 3-hydroxy-2-stearamidooctadecane-1-sulfonic acid

S-(2R,3R) 3-(tert-butyldimethylsilyloxy)-2-stearamidooctadecyl ethanethioate

N-((2S,3R) 3-(tert-butyldimethylsilyloxy)-1-hydroxyoctadecan-2-yl)stearamide

Refernces

• 1、 -. "METHOD FOR PRODUCING HIGH-PURITY CERAMIDE". Paragraph 0052; 0053. . Retrieved 2014/11/13.
• 2、 Chang, Young-Tae,Choi, Jaehwa,Ding, Sheng,Prieschl, Eva E.,Baumruker, Thomas,Lee, Jae-Mok,Chung, Sung-Kee,Schultz, Peter G.. "The synthesis and biological characterization of a ceramide library". . p. 1856 - 1857. Retrieved 2007/10/03.