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S4257

Sigma-Aldrich

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

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About This Item

Empirical Formula (Hill Notation):
C23H49N2O5P
CAS Number:
Molecular Weight:
464.62
Beilstein:
7342520
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

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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).

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

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