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S4257

Sigma-Aldrich

Sphingosylphosphorylcholine

≥98%, powder

Sinônimo(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

Fórmula empírica (Notação de Hill):
C23H49N2O5P
Número CAS:
1670-26-4
Peso molecular:
464.62
Beilstein:
7342520
Número MDL:
MFCD02259287
Código UNSPSC:
12352211
ID de substância PubChem:
24899596
NACRES:
NA.77

Nível de qualidade

200

Ensaio

≥98%

Formulário

powder

cor

light yellow

solubilidade

chloroform/methanol (2:1): complete 10 mg/ml, clear to slightly hazy, colorless to light yellow

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

[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

chave InChI

JLVSPVFPBBFMBE-HXSWCURESA-N

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Aplicação

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

Ações bioquímicas/fisiológicas

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).

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)

Escolha uma das versões mais recentes:

Certificados de análise (COA)

Lot/Batch Number
059M4102V
14181108
118M4131V
14180105
088M4132V

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Sphingosine 1-phosphate ≥95%, powder

Sigma-Aldrich

S9666

Sphingosine 1-phosphate

α-L-Iduronidase human recombinant, expressed in mouse NSO cells

Sigma-Aldrich

I6034

α-L-Iduronidase human

Monosialoganglioside GM2 from bovine brain ≥95% (TLC)

Sigma-Aldrich

G8397

Monosialoganglioside GM2 from bovine brain

Egg SM Avanti Research™ - A Croda Brand

Avanti

860061P

Egg SM

Sphingosine-1-Phosphate (d18:1) Avanti Research™ - A Croda Brand

Avanti

860492P

Sphingosine-1-Phosphate (d18:1)

18:1 Lyso PC Avanti Research™ - A Croda Brand

Avanti

845875P

18:1 Lyso PC

12:0 PC (DLPC) Avanti Research™ - A Croda Brand

Avanti

850335P

12:0 PC (DLPC)

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
D Meyer zu Heringdorf et al.
FEBS letters, 410(1), 34-38 (1997-06-23)
Sphingolipid breakdown products are now being recognized to play a dual role in cellular signalling, acting as intracellular as well as extracellular signalling molecules. Both types of action may even be found with one sphingolipid species. The recent demonstration of
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
Ha Young Lee et al.
Journal of immunology (Baltimore, Md. : 1950), 186(7), 4347-4353 (2011-03-04)
Sphingosylphosphorylcholine (SPC) is a component of high-density lipoprotein particles. We investigated the functional role of SPC in HUVECs. SPC stimulation induced production of the CCL2 chemokine in a PTX-sensitive G-protein-dependent manner. SPC treatment caused the activation of NF-κB and AP-1
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