SPHINGOSYLPHOSPHORYLCHOLINE

Synonym(s):Sphingosylphosphorylcholine;(2S,3R,4E)-2-Amino-4-octadecene-3-hydroxy-1-phosphocholine;D-erythro-Sphingosine phosphocholine;2-[[[(2-Amino-3-hydroxy-4-octadecenyl)oxy]hydroxy-phosphinyl]oxy]-N,N,N-trimethylethanaminium inner salt;Lyso SM (d18:1)

CAS NO.：1670-26-4
Empirical Formula: C23H49N2O5P
Molecular Weight: 464.62
MDL number: MFCD02259287
SAFETY DATA SHEET (SDS)
Update Date: 2024-10-28 23:16:16

What is SPHINGOSYLPHOSPHORYLCHOLINE?

Chemical properties

Yellowish Waxy Solid

The Uses of SPHINGOSYLPHOSPHORYLCHOLINE

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

The Uses of SPHINGOSYLPHOSPHORYLCHOLINE

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.

The Uses of SPHINGOSYLPHOSPHORYLCHOLINE

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 bilayers
as an inhibitor of Ca²⁺sensor calmodulin (CaM)
as a standard in circular dichroism (CD) spectroscopy to determine lipid selectivity of the lipid-peptide interactions

What are the applications of Application

Sphingosylphosphorylcholine, D-erythro is a sphingosine metabolite and activator of a variety of pathways

Definition

ChEBI: Sphingosine-1-phosphocholine is a phosphosphingolipid consisting of sphingosine having a phosphocholine moiety attached to its primary hydroxyl group. It is a phosphosphingolipid, a member of phosphocholines and an ammonium betaine. It is functionally related to a sphingosine. It is a conjugate base of a sphingosylphosphocholine acid and a sphingosine-1-phosphocholine(1+).

General Description

Lyso SM (d18:1), also known as sphingosylphosphorylcholine (SPC), is a bioactive lipid molecule. This lysophospholipid is present in normal blood plasma, ascites and various tissues.

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).

Properties of SPHINGOSYLPHOSPHORYLCHOLINE

Melting point:	90-102°C
storage temp.	-20°C
solubility	chloroform/methanol (2:1): complete10 mg/ml, clear to slightly hazy, colorless to light yellow
form	powder
color	light yellow
BRN	7342520