Sphingosyl-phosphocholine

Base Information

• Chemical Name: Sphingosyl-phosphocholine
• CAS No.: 1670-26-4
• Molecular Formula: C23H49N2O5P
• Molecular Weight: 464.626
• ChEMBL ID: CHEMBL1236027
• Nikkaji Number: J619.421D,J3.144.218D
• Wikidata: Q27465452
• Mol file: 1670-26-4.mol

Synonyms:lysosphingomyelin;sphingosine phosphorylcholine;sphingosylphosphocholine;sphingosylphosphorylcholine

Chemical Property of Sphingosyl-phosphocholine

Chemical Property:

• Melting Point: 90-102°C
• PSA: 114.65000
• LogP: 5.91020
• Storage Temp.: −20°C
• Solubility.: chloroform/methanol (2:1): complete10 mg/ml, clear to slightly h
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 21
• Exact Mass: 465.34573470
• Heavy Atom Count: 31
• Complexity: 497

Purity/Quality:

98%,99%, ^*data from raw suppliers

SPC ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCC=CC(C(COP(=O)(O)OCC[N+](C)(C)C)N)O
• Isomeric SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](COP(=O)(O)OCC[N+](C)(C)C)N)O
• Uses: Involved in cell regulation, and transmembrane signaling. A putative lipid second messenger, connected via Protein Kinase C to the phosphatidylinositol-derived second messengers for signal transduction. Neurotrophic effects of Sphingosylphosphorylcholine were studied in cerebellar granule neurons of mice and PC-12 cells. Lyso SM (d18:1) has been used: to study its effect on the skeletal muscle ryanodine receptor (RyR1), in the presence and absence of calmodulin through single channel recordings in planar lipid bilayersas an inhibitor of Ca2+ sensor calmodulin (CaM)as a standard in circular dichroism (CD) spectroscopy to determine lipid selectivity of the lipid-peptide interactions

Technology Process of Sphingosyl-phosphocholine

There total 15 articles about Sphingosyl-phosphocholine 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: 79.5%

→ 2-butyl-1,3-diaza-spiro[4.4]non-1-en-4one (138402-05-8) + sphingosylphosphorylcholine (1670-26-4,105615-55-2,82970-80-7)

Guidance literature:

Reference yield: 73.0%

(E,2S,3R)-2-azido-3-hydroxyoctadec-4-en-1-yl 2-(trimethylammonio)ethyl phosphate → sphingosylphosphorylcholine (1670-26-4,105615-55-2,82970-80-7)

Guidance literature:

With 1.3-propanedithiol; triethylamine; In methanol; at 20 ℃; for 72h; Inert atmosphere;

DOI:10.1055/s-0039-1690863

Reference yield: 51.0%

→ SPC*HCl + sphingosylphosphorylcholine (1670-26-4,105615-55-2,82970-80-7)

Guidance literature:

upstream raw materials:

<(2S,3R,4E)-2-amino-3-(tert-butyldimethylsilyloxy)-4-octadecene-1-yl><2-(trimethylammonio)ethyl> phosphate

(4S)-4-[(1R)-1-(tert-butyldiphenylsilyloxy)-hexadec-2-enyl]-2-chloro-2-oxo-[1,3,2]-oxazaphospholidine

choline tosylate

(2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol

Downstream raw materials:

C₆₅H₈₈F₄N₅O₁₄PS₂

N-perdeuteriopalmitoylsphingomyelin

2-methyl-3-buten-2-ol

Refernces

• 1、 -. "SPHINGOMYELIN, INTERMEDIATES THEREOF AND METHODS FOR PREPARATION OF SAME". Page/Page column 20-21. . Retrieved 2010/02/13.
• 2、 Kratzer, Bernd,Schmidt, Richard R.. "Efficient Synthesis of Sphingosine-1-phosphate, Ceramide-1-phosphate, Lysosphingomyelin, and Sphingomyelin". . p. 957 - 964. Retrieved 2007/10/02.