Molecular structure of C-8 Ceramide, CAS Number: 74713-59-0
C-8 Ceramide (CAS 74713-59-0)
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Alternate Names:
N-octanoylsphingosine; N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-octanamide
Application:
C-8 Ceramide is a ceramide analog
CAS Number:
74713-59-0
Purity:
>98%
Molecular Weight:
425.5
Molecular Formula:
C26H51NO3
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
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.
C-8 Ceramide (CAS 74713-59-0) References
- Ceramides modulate protein kinase C activity and perturb the structure of Phosphatidylcholine/Phosphatidylserine bilayers. | Huang, HW., et al. 1999. Biophys J. 77: 1489-97. PMID: 10465759
- Sphingomyelinase and ceramide analogs induce contraction and rises in [Ca(2+)](i) in canine cerebral vascular muscle. | Zheng, T., et al. 2000. Am J Physiol Heart Circ Physiol. 278: H1421-8. PMID: 10775118
- DAP kinase activity is critical for C(2)-ceramide-induced apoptosis in PC12 cells. | Yamamoto, M., et al. 2002. Eur J Biochem. 269: 139-47. PMID: 11784307
- Intracellular delivery of ceramide lipids via liposomes enhances apoptosis in vitro. | Shabbits, JA. and Mayer, LD. 2003. Biochim Biophys Acta. 1612: 98-106. PMID: 12729935
- Ceramide induces caspase-dependent and -independent apoptosis in A-431 cells. | Zhao, S., et al. 2004. J Cell Physiol. 199: 47-56. PMID: 14978734
- Sphingomyelinase causes endothelium-dependent vasorelaxation through endothelial nitric oxide production without cytosolic Ca(2+) elevation. | Mogami, K., et al. 2005. FEBS Lett. 579: 393-7. PMID: 15642349
- Preparation and characterization of ceramide-based liposomes with high fusion activity and high membrane fluidity. | Tokudome, Y., et al. 2009. Colloids Surf B Biointerfaces. 73: 92-6. PMID: 19487111
- Ceramide regulates gemcitabine-induced senescence and apoptosis in human pancreatic cancer cell lines. | Modrak, DE., et al. 2009. Mol Cancer Res. 7: 890-6. PMID: 19531570
- Expression of calcium-sensing receptor in quail granulosa explants: a key to survival during folliculogenesis. | Diez-Fraile, A., et al. 2010. Anat Rec (Hoboken). 293: 890-9. PMID: 20186967
- Prohibitin (PHB) acts as a potent survival factor against ceramide induced apoptosis in rat granulosa cells. | Chowdhury, I., et al. 2011. Life Sci. 89: 295-303. PMID: 21763324
- Acidic sphingomyelinase-generated ceramide is needed but not sufficient for TNF-induced apoptosis and nuclear factor-kappa B activation. | Higuchi, M., et al. 1996. J Immunol. 157: 297-304. PMID: 8683130
- Ceramide-induced translocation of protein kinase C zeta in primary cultures of astrocytes. | Galve-Roperh, I., et al. 1997. FEBS Lett. 415: 271-4. PMID: 9357981
Inhibitor of:
FAR1, LASS2, ORMDL2, and PAP-2c.Activator of:
Apaf-1, CD300LD, Elastase-2, ENDOG, EVPLL, GCET2, GD3 Synthase, GM2/GD2 Synthase, HTLV-1 Tax, INPP5J, MORN4, neurolysin, ORMDL1, PKC, PKC λ/Δ, PKN, PLBD1, SMPD5, SPTLC1, St3Gal-I, ST8Sia III, and TMSL3.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
C-8 Ceramide, 1 mg | sc-205233 | 1 mg | $19.00 | |||
C-8 Ceramide, 5 mg | sc-205233A | 5 mg | $63.00 | |||
C-8 Ceramide, 25 mg | sc-205233B | 25 mg | $228.00 |