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860600P

Avanti

Lyso SM (d18:1)

Avanti Research™ - A Croda Brand 860600P, powder

Synonym(s):

Sphingosylphosphorylcholine

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About This Item

Empirical Formula (Hill Notation):
C23H49N2O5P
CAS Number:
1670-26-4
Molecular Weight:
464.62
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 10 mg (860600P-10mg)
pkg of 1 × 25 mg (860600P-25mg)
pkg of 1 × 5 mg (860600P-5mg)
pkg of 1 × 50 mg (860600P-50mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 860600P

lipid type

sphingolipids

shipped in

dry ice

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

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.

Application

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

Biochem/physiol Actions

Lyso SM (d18:1) or sphingosylphosphorylcholine (SPC) is a lipid mediator that exhibits second messenger functions. It regulates ryanodine receptors (RyRs) and releases Ca2+ from the sarco/endoplasmic reticulum. Lyso SM (d18:1) acts as an endogenous inhibitor of ubiquitous Ca2+ sensor calmodulin (CaM).

Packaging

5 mL Amber Glass Screw Cap Vial (860600P-10mg)
5 mL Amber Glass Screw Cap Vial (860600P-25mg)
5 mL Amber Glass Screw Cap Vial (860600P-50mg)
5 mL Amber Glass Screw Cap Vial (860600P-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

Sigma-Aldrich

I2521

ITS+1 Liquid Media Supplement (100×)

Dagmar Meyer zu Heringdorf et al.
Biochimica et biophysica acta, 1582(1-3), 178-189 (2002-06-19)
Compared to the lysophospholipid mediators, sphingosine-1-phosphate (S1P) and lysophosphatidic acid (LPA), little information is available regarding the molecular mechanisms of action, metabolism and physiological significance of the related sphingosylphosphorylcholine (SPC). S1P and LPA have recently been established as agonists at
Erika Kovacs et al.
Biochemical and biophysical research communications, 401(2), 281-286 (2010-09-21)
Sphingosylphosphorylcholine (SPC), a lipid mediator with putative second messenger functions, has been reported to regulate ryanodine receptors (RyRs), Ca2+ channels of the sarco/endoplasmic reticulum. RyRs are also regulated by the ubiquitous Ca2+ sensor calmodulin (CaM), and we have previously shown
Sphingosylphosphorylcholine and lysophosphatidylcholine are ligands for the G protein-coupled receptor GPR4.
The Journal of biological chemistry, 280(52), 43280-43280 (2006-02-25)
Tomokazu Yasuda et al.
Langmuir : the ACS journal of surfaces and colloids, 34(44), 13426-13437 (2018-10-24)
In this study, we applied fluorescence spectroscopy, differential scanning calorimetry (DSC), and 2H NMR to elucidate the properties of nanoscopic segregated domains in stearoylsphingomyelin (SSM)/dioleoylphosphatidylcholine (DOPC) and dihydrostearoylsphingomyelin (dhSSM)/DOPC binary membranes. The results obtained from fluorescence measurements suggest the existence
Caius G Radu et al.
Proceedings of the National Academy of Sciences of the United States of America, 101(1), 245-250 (2003-12-19)
G2A is an immunoregulatory G protein-coupled receptor predominantly expressed in lymphocytes and macrophages. Ectopic overexpression studies have implicated G2A as a receptor for the bioactive lysophospholipid, lysophosphatidylcholine (LPC). However, the functional consequences of LPC-G2A interaction at physiological levels of receptor
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