C-8 CeramideA ceramide analog

C-8 Ceramide (CAS 74713-59-0)

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Synonym: N-octanoylsphingosine; N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-octanamide
Application: A ceramide analog
CAS Number: 74713-59-0
Purity: >98%
Molecular Weight: 425.5
Molecular Formula: C26H51NO3
* Refer to Certificate of Analysis for lot specific data (including water content).
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C-8 Ceramide is a cell-permeable analog of naturally occurring ceramides where unlike C-2 ceramide, it is metabolized within cells to generate natural ceramides, often causing a dramatic increase in cellular ceramide levels. For this reason, treatment of cells with C-8 Ceramide may more closely mimic the effects of ceramide elevation than does treatment with shorter chain ceramide analogs. C-8 Ceramide likely mediates many diverse biological activities, as do natural ceramides. It induces apoptosis of both human leukemia cells and the U937 cell line,1,3 and promotes the differentiation of human keratinocytes. C-8 Ceramide is an activator of PKC.


References

1 Karasavvas, N., Erukulla, R.K., Bittman, R., et al. Stereospecific induction of apoptosis in U937 cells by N-octanoyl-sphingosine stereoisomers and N-octyl-sphingosine. The ceramide amide group is not required for apoptosis. Eur J Biochem 236 729-737 (1996). 2 Wakita, H., Tokura, Y., Yagi, H., et al. Keratinocyte differentiation is induced by cell-permeant ceramides and its proliferation is promoted by sphingosine. Arch Dermatol Res 286 350-354 (1994). 3 Geley, S., Hartmann, B.L., Kofler, R. Ceramides induce a form of apoptosis in human acute lymphoblastic leukemia cells that is inhibited by Bcl-2, but not by CrmA. FEBS Lett 400 15-18 (1997).

Physical State :
Solid
Solubility :
Soluble in DMSO (25 mg/ml), methanol, DMF (~20 mg/ml), and 100% ethanol (25 mg/ml).
Storage :
Store at -20° C
Melting Point :
246.71° C (Predicted)
Boiling Point :
~595.5° C at 760 mmHg (Predicted)
Density :
~0.9 g/cm3 (Predicted)
Refractive Index :
n20D 1.48 (Predicted)
IC50 :
MCF7: IC50 = 1.2 µM (human); MDA-MB-231: IC50 = 1.8 µM (human); ADMET: EC5050 = 11 µM; Trypanosoma cruzi: EC5050 = 13 µM
pK Values :
pKa: 13.55 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
PubChem CID :
5702614
MDL Number :
MFCD00236496
SMILES :
CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)NC(=O)CCCCCCC)O

Download SDS (MSDS)

Certificate of Analysis

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