376650
D-erythro-Sphingosine, N-Hexanoyl-
Biologically active, cell-permeable, non-physiological ceramide analog.
Synonym(s):
D-erythro-Sphingosine, N-Hexanoyl-, C6 Ceramide
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About This Item
Empirical Formula (Hill Notation):
C24H47NO3
CAS Number:
Molecular Weight:
397.63
UNSPSC Code:
12352211
NACRES:
NA.77
MDL number:
Assay:
≥98% (TLC)
Form:
waxy solid
Storage condition:
OK to freeze
Quality Segment
assay
≥98% (TLC)
form
waxy solid
manufacturer/tradename
Calbiochem®
storage condition
OK to freeze
color
white
solubility
ethanol: 25 mg/mL, DMSO: soluble
shipped in
ambient
storage temp.
−20°C
SMILES string
N(C(C(O)\C=C\CCCCCCCCCCCCC)CO)C(=O)CCCCC
InChI
1S/C24H47NO3/c1-3-5-7-8-9-10-11-12-13-14-15-16-18-19-23(27)22(21-26)25-24(28)20-17-6-4-2/h18-19,22-23,26-27H,3-17,20-21H2,1-2H3,(H,25,28)/b19-18+
InChI key
NPRJSFWNFTXXQC-VHEBQXMUSA-N
General description
Biologically active, cell-permeable, non-physiological ceramide analog. Induces a dramatic arrest in the G0/G1 phase of the cell cycle. Activates MAP kinase. Activates protein phosphatase 2A (PP2A) at 10 nM. Inhibits diacylglycerol accumulation and phospholipase D (PLD) activation in fibroblasts. Induces apoptosis in MOLT-4 leukemia cells.
Biologically active, cell-permeable, nonphysiological ceramide analog. Stimulates cytosolic serine/threonine protein phosphatase in T9 cells and induces phosphorylation on Thr-669 in A-431 cells by stimulation of ceramide-activated protein kinase. Induces a dramatic arrest in the Go/G1 phase of the cell cycle. Activates MAP kinase. Activates protein phosphatase 2A (PP2A) at 10 nM. Inhibits diacylglycerol accumulation and phospholipase D activation in fibroblasts. Induces apoptosis in Molt-4 leukemia cells.
Biochem/physiol Actions
Cell permeable: yes
Effective concentration: 10 nM in activating protein phosphatase 2A (PP2A)
Primary Target
MAP kinase, protein phosphatase 2A (PP2A)
MAP kinase, protein phosphatase 2A (PP2A)
Product does not compete with ATP.
Reversible: no
Preparation Note
Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 2 months at -20°C.
Other Notes
Jayadev, S., et al. 1995. J. Biol. Chem. 270, 2047.
Venable, M.E., et al. 1994. J. Biol. Chem. 269, 26040.
Dobrowsky, R.T., et al. 1993. J. Biol. Chem. 268, 15523.
Raines, M.A., et al. 1993. J. Biol. Chem.268, 14572.
Dobrowsky, R.T., and Hannun, Y.A. 1992. J. Biol. Chem.267, 5048.
Venable, M.E., et al. 1994. J. Biol. Chem. 269, 26040.
Dobrowsky, R.T., et al. 1993. J. Biol. Chem. 268, 15523.
Raines, M.A., et al. 1993. J. Biol. Chem.268, 14572.
Dobrowsky, R.T., and Hannun, Y.A. 1992. J. Biol. Chem.267, 5048.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Disclaimer
Toxicity: Irritant (B)
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Certificates of Analysis (COA)
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Global Trade Item Number
| SKU | GTIN |
|---|---|
| 376650-5MG | 04055977212952 |