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567735

Sigma-Aldrich

Sphingosylphosphoryl-choline

SPC is the deacylated derivative of sphingomyelin known to accumulate in neuropathic Niemann-Pick disease type A.

Synonym(s):

Sphingosylphosphoryl-choline, SPC, lyso-Sphingomyelin

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About This Item

Empirical Formula (Hill Notation):
C23H49N2O5P
CAS Number:
Molecular Weight:
464.62
MDL number:
UNSPSC Code:
12352211
NACRES:
NA.77

Quality Level

assay

≥98% (TLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
desiccated

color

white

solubility

chloroform/methanol (2:1): 1 mg/mL

shipped in

ambient

storage temp.

−20°C

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

SPC is the deacylated derivative of sphingomyelin known to accumulate in neuropathic Niemann-Pick disease type A. A potent mitogen that increases intracellular free Ca2+ and free arachidonate through pathways that are only partially PKC-dependent. Stimulates DNA-binding activity of the transcription activator protein AP-1. Rapidly induces tyrosine phosphorylation of focal adhesion kinase (p125FAK) and paxillin and causes a rapid and transient activation of MAP kinase in Swiss/3T3 cells. Also induces a unique reorganization of the actin cytoskeleton.
SPC is the deacylated derivative of sphingomyelin known to accumulate in neuropathic Niemann-Pick disease type A. A potent mitogen that increases intracellular free Ca2+ and free arachidonate through pathways that are only partially PKC-dependent. Stimulates DNA-binding activity of the transcription activator protein AP-1. Rapidly induces tyrosine phosphorylation of focal adhesion kinase (p125FAK) and paxillin and causes a rapid and transient activation of MAP kinase in Swiss 3T3 cells. Also induces a unique reorganization of the actin cytoskeleton.

Biochem/physiol Actions

Cell permeable: no
Primary Target
A potent mitogen
Product does not compete with ATP.
Reversible: no

Warning

Toxicity: Standard Handling (A)

Reconstitution

Following initial thaw, aliquot and freeze (-20°C). Stock solutions are stable for up to 2 months at -20°C.

Other Notes

Berger, A., et al. 1995. Proc. Natl. Acad. Sci. USA 92, 5885.
Dettbarn, C., et al. 1995. Brain Res.669, 79.
Seufferlein, T. and Rozengurt, E. 1995. J. Biol. Chem. 270, 24343.
Seufferlein, T. and Rozengurt, E. 1995. J. Biol. Chem. 270, 24334.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

wgk_germany

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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