Sphingosine

Base Information

• Chemical Name: Sphingosine
• CAS No.: 123-78-4
• Molecular Formula: C18H37NO2
• Molecular Weight: 299.497
• Hs Code.: 29221985
• European Community (EC) Number: 204-651-3
• UNII: 0Y6SVQ612Q,NGZ37HRE42
• DSSTox Substance ID: DTXSID90861763
• Nikkaji Number: J36.270K,J10.894D,J1.627.151I
• Wikipedia: Sphingosine
• Wikidata: Q46298
• Pharos Ligand ID: 8BM32XZ1PNMB
• Metabolomics Workbench ID: 30474
• ChEMBL ID: CHEMBL67166
• Mol file: 123-78-4.mol

Synonyms:4 Sphingenine;4-Sphingenine;Sphingosine

Chemical Property of Sphingosine

Chemical Property:

• Appearance/Colour: White crystalline solid
• Vapor Pressure: 7.96E-10mmHg at 25°C
• Melting Point: 81-82 °C
• Refractive Index: 1.489
• Boiling Point: 445.922 °C at 760 mmHg
• PKA: 11.80±0.45(Predicted)
• Flash Point: 223.486 °C
• PSA: 66.48000
• Density: 0.94 g/cm³
• LogP: 4.62450
• Storage Temp.: −20°C
• Solubility.: chloroform: 20 mg/mL, clear, colorless to very faintly yell
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 15
• Exact Mass: 299.282429423
• Heavy Atom Count: 21
• Complexity: 231

Purity/Quality:

99% ^*data from raw suppliers

Sphingosine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCCCCCCCCCC=CC(C(CO)N)O
• Isomeric SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)N)O
• Description: Sphingosine (123-78-4) is an inhibitor of protein kinase C (IC50 = 1-3 μM).1 It is abundant in cell membranes and is an important mediator in various biochemical pathways.2-4
• Uses: Selective inhibitor of protein kinase C activity and phorbol dibutyrate binding in vitro in human platelets; does not inhibit protein kinase A or myosin light chain kinase; inhibits calmodulin-dependent enzymes; natural isomer of sphingosine D-erythro-Sphingosine is used to inhibits protein kinase C and calmodulin-dependent enzymes, induces apoptosis. And also used to constituent of cell membranes. Sphingosine (d18:1) has been used:for sphingosine inhalations studies in mice to evaluate its therapeutic potential in respiratory epithelial cellsto investigate its effect on Pseudomonas aeruginosa strainsas a standard in liquid chromatography tandem mass spectrophotometry for the quantification of epidermal ceramides

Technology Process of Sphingosine

There total 208 articles about Sphingosine 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: 100.0%

N-tert-butyloxycarbonylsphingosine (116467-63-1) → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

Guidance literature:

N-tert-butyloxycarbonylsphingosine; With trifluoroacetic acid; In dichloromethane; at 50 ℃; for 2h;

With sodium hydroxide; water; In dichloromethane; pH=~ 10;

Reference yield: 100.0%

(2'E,4S,1'R)-4-(1'-hydroxyhexadec-2'-enyl)-1,3-oxazolidin-2-one (105308-75-6) → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

Guidance literature:

With sodium hydroxide; ethanol; at 80 ℃; for 2.5h;

DOI:10.1021/jo00389a035

Reference yield: 99.0%

tert-butyl ((2S,3R,E)-1-((tert-butyldimethylsilyl)oxy)-3-hydroxy-octadec-4-en-2-yl)carbamate (221455-36-3) → (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 1.5h;

DOI:10.1016/j.bioorg.2020.103703

upstream raw materials:

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

N-Ethoxycarbonyl-trans-sphingosine

N-acetyl-D-erythro-sphingosine

(2S,3R,4E)-2-acetamido-1,3-diacetoxyoctadec-4-ene

Downstream raw materials:

N-lauroylceramide

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

N-CBZ-dihydrosphingosine

tridecanoic acid

Refernces

Synthesis of a prenylated and immunosuppressive marine galactosphingolipid with cyclopropane-containing alkyl chains: (2S,3R,11S,12R,2?R,5?Z,11?S,12?R)-Plakoside A and its (2S,3R,11R,12S,2?R,5?Z,11?R,12?)Isomer

10.1002/1099-0690(200110)2001:20<3797::AID-EJOC3797>3.0.CO;2-Y

The study presents a detailed account of the synthesis of Plakoside A, a prenylated and immunosuppressive marine galactosphingolipid isolated from the marine sponge Plakortis simplex. The research involves the synthesis of two diastereoisomers of Plakoside A, which are structurally unique glycosphingolipids containing a prenylated D-galactose moiety and cyclopropane-containing alkyl chains. The study utilized a variety of chemicals, including sphingosine, α-hydroxy acids, prenylated sugars, and various reagents for protection and deprotection of functional groups, as well as for the construction of the complex molecular framework. These chemicals served the purpose of constructing the three main building blocks of Plakoside A: the sugar part, the sphingosine part, and the hydroxy acid part. The synthesis involved multiple steps, including enzymatic methods, Wittig reactions, and prenylation, with the ultimate goal of obtaining the target compounds and elucidating their absolute configuration.

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