SPHINGOSYLPHOSPHORYLCHOLINE Chemical Properties

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

Safety Information

WGK Germany 

3

F 

1-8-10

MSDS

• Language:English Provider:SigmaAldrich

SPHINGOSYLPHOSPHORYLCHOLINE Usage And Synthesis

Chemical Properties

Yellowish Waxy Solid

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.

Uses

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

Uses

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

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).

SPHINGOSYLPHOSPHORYLCHOLINE(1670-26-4)Related Product Information

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