Date published: 2026-4-24

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N-Stearoyl-D-Sphingosine (CAS 2304-81-6)

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Alternate Names:
N-Stearoyl ceramide (synthetic), C18-Ceramide (synthetic)
Application:
N-Stearoyl-D-Sphingosine is an inhibitor of the mitochondrial permeability transition pore
CAS Number:
2304-81-6
Purity:
≥95%
Molecular Weight:
565.9
Molecular Formula:
C36H71NO3
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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N-Stearoyl-D-sphingosine, a synthesized sphingolipid, incorporates a stearoyl fatty acid chain into the natural sphingosine backbone, enhancing its hydrophobicity and impact on lipid membrane characteristics. This modification imbues N-Stearoyl-D-sphingosine with distinct biophysical properties, crucial for studying the structural dynamics and functional roles of ceramides and related sphingolipids in cellular membranes. In research contexts, this compound is extensively utilized to dissect the interactions within lipid bilayers, particularly focusing on how these sphingolipids influence membrane fluidity, phase behavior, and the formation of lipid rafts. These rafts are essential microdomains that facilitate various cellular processes, including signal transduction and molecular sorting. N-Stearoyl-D-sphingosine′s ability to integrate into cellular membranes allows researchers to explore its effect on the organization and stabilization of membrane-associated proteins and signaling complexes. Additionally, its role in modulating the physicochemical properties of membranes provides insights into the molecular basis of membrane integrity and functionality. Through such investigations, N-Stearoyl-D-sphingosine serves as a valuable tool in biophysical and cell biology research, helping to explain the fundamental mechanisms by which sphingolipids contribute to cellular homeostasis and the regulation of cellular responses to external stimuli.


N-Stearoyl-D-Sphingosine (CAS 2304-81-6) References

  1. Structural analysis of commercial ceramides by gas chromatography-mass spectrometry.  |  Bleton, J., et al. 2001. J Chromatogr A. 917: 251-60. PMID: 11403477
  2. Coupled assay of sphingomyelin and ceramide molecular species by gas liquid chromatography.  |  Vieu, C., et al. 2002. J Lipid Res. 43: 510-22. PMID: 11893787
  3. Structure-retention diagrams of ceramides established for their identification.  |  Gaudin, K., et al. 2002. J Chromatogr A. 973: 69-83. PMID: 12437165
  4. Simultaneous quantitative determination method for ceramide species from crude cellular extracts by high-performance liquid chromatography-thermospray mass spectrometry.  |  Yamane, M. 2003. J Chromatogr B Analyt Technol Biomed Life Sci. 783: 181-90. PMID: 12450537
  5. Sphingolipids suppress preneoplastic rat hepatocytes in vitro and in vivo.  |  Silins, I., et al. 2003. Carcinogenesis. 24: 1077-83. PMID: 12807752
  6. Involvement of ceramide in ischemic tolerance induced by preconditioning with sublethal oxygen-glucose deprivation in primary cultured cortical neurons of rats.  |  Bhuiyan, MI., et al. 2010. Biol Pharm Bull. 33: 11-7. PMID: 20045928
  7. Increases in phosphatidic acid levels accompany sphingosine-stimulated proliferation of quiescent Swiss 3T3 cells.  |  Zhang, H., et al. 1990. J Biol Chem. 265: 21309-16. PMID: 2250025
  8. Sphingomyelin synthase-related protein generates diacylglycerol via the hydrolysis of glycerophospholipids in the absence of ceramide.  |  Murakami, C. and Sakane, F. 2021. J Biol Chem. 296: 100454. PMID: 33621517
  9. Diacylglycerol kinase ζ interacts with sphingomyelin synthase 1 and sphingomyelin synthase-related protein via different regions.  |  Furuta, M., et al. 2023. FEBS Open Bio. 13: 1333-1345. PMID: 37166445

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

N-Stearoyl-D-Sphingosine, 1 mg

sc-211176
1 mg
$24.00

N-Stearoyl-D-Sphingosine, 5 mg

sc-211176A
5 mg
$78.00