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Merck

S4257

Sigma-Aldrich

Sphingosylphosphorylcholine

≥98%, powder

Synonim(y):

(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

Wzór empiryczny (zapis Hilla):
C23H49N2O5P
Numer CAS:
Masa cząsteczkowa:
464.62
Beilstein:
7342520
Numer MDL:
Kod UNSPSC:
12352211
Identyfikator substancji w PubChem:
NACRES:
NA.77

Poziom jakości

Próba

≥98%

Postać

powder

kolor

light yellow

rozpuszczalność

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

temp. przechowywania

−20°C

ciąg 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

Klucz InChI

JLVSPVFPBBFMBE-HXSWCURESA-N

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Zastosowanie

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

Działania biochem./fizjol.

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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Kod klasy składowania

11 - Combustible Solids

Klasa zagrożenia wodnego (WGK)

WGK 3

Temperatura zapłonu (°F)

Not applicable

Temperatura zapłonu (°C)

Not applicable

Środki ochrony indywidualnej

Eyeshields, Gloves, type N95 (US)


Certyfikaty analizy (CoA)

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Dokumenty związane z niedawno zakupionymi produktami zostały zamieszczone w Bibliotece dokumentów.

Odwiedź Bibliotekę dokumentów

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
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
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
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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