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S4257

Sphingosylphosphorylcholine

≥98%, intracellular and extracellular signaling mediator, 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:
1670-26-4
Molecular Weight:
464.62
NACRES:
NA.77
PubChem Substance ID:
24899596
UNSPSC Code:
12352211
MDL number:
MFCD02259287
Beilstein/REAXYS Number:
7342520
Assay:
≥98%
Form:
powder
Quality level:
200
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Product Name

Sphingosylphosphorylcholine, ≥98%, powder

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

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).

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000520154
0000520154
0000476614
0000447860
0000447860

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Naoko Konno et al.
Biochemical and biophysical research communications, 364(1), 163-168 (2007-10-16)
Sphingosylphosphorylcholine (SPC) is a choline-containing naturally occurring derivative of sphingolipid involved in various biological processes. Here we show that SPC displays neurotrophic effects in cerebellar granule neurons (CGNs) and in PC12 cells. When CGNs were cultured under non-depolarizing condition, they
H Okamoto et al.
Biochemical and biophysical research communications, 260(1), 203-208 (1999-06-25)
AGR16/H218/EDG5 and EDG1 are functional receptors for lysosphingolipids, whereas EDG2 and EGD4 are receptors for lysophosphatidic acid (LPA). The present study demonstrates that EDG3, the yet poorly defined member of the EDG family G protein-coupled receptors, shows identical agonist specificity
A Uehara et al.
FEBS letters, 460(3), 467-471 (1999-11-11)
The effects of the lysosphingolipid, sphingosylphosphorylcholine (SPC), on the cardiac ryanodine receptor (RyR) were examined. The open probability of cardiac RyR incorporated in lipid bilayers was decreased by cytoplasmic, but not lumenal side application of micromolar concentrations of SPC. Modification
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Global Trade Item Number

SKUGTIN
S4257-10MG04061836925598
S4257-25MG04061836925611