S4257

Sphingosylphosphorylcholine

≥98%, powder

• Synonym(s): (2S,3R,4E)-2-Amino-4-octadecene-3-hydroxy-1-phosphocholine, 2-[[[(2-Amino-3-hydroxy-4-octadecenyl)oxy]hydroxy-phosphinyl]oxy]-N,N,N-trimethylethanaminium inner salt, D-erythro-Sphingosine phosphocholine, Lyso SM (d18:1), Lysosphingomyelin
• Empirical Formula (Hill Notation): C₂₃H₄₉N₂O₅P
• CAS Number: 1670-26-4
• Molecular Weight: 464.62
• Beilstein: 7342520
• MDL number: MFCD02259287
• UNSPSC Code: 12352211
• PubChem Substance ID: 24899596
• NACRES: NA.77

Properties

• Quality Level: 200
• Assay: ≥98%
• form: powder
• color: light yellow
• solubility: chloroform/methanol (2:1): complete 10 mg/ml, clear to slightly hazy, colorless to light yellow
• storage temp.: −20°C
• SMILES string: [H][C@](/C=C/CCCCCCCCCCCCC)(O)[C@@]([H])(N)COP([O-])(OCC[N+](C)(C)C)=O
• InChI: 1S/C23H49N2O5P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(26)22(24)21-30-31(27,28)29-20-19-25(2,3)4/h17-18,22-23,26H,5-16,19-21,24H2,1-4H3/b18-17+/t22-,23+/m0/s1
• InChI key: JLVSPVFPBBFMBE-HXSWCURESA-N

Description

Application

Neurotrophic effects of Sphingosylphosphorylcholine were studied in cerebellar granule neurons of mice and PC-12 cells.

Biochem/physiol Actions

Sphingosylphosphorylcholine (SPC) is a bioactive lipid that mediates intracellular and extracellular signaling. It mobilizes Ca²⁺ from intracellular stores via an IP3-independent pathway. It stimulates the production of CCL2 that may contribute to development of atherosclerosis. SPC is a ligand for endothelial differentiation gene receptor 3 (EDG3).

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves