C-16 Ceramide
Item № 10681
CAS № 24696-26-2
Purity ≥98%
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5 mg $45.00 $0.00
10 mg $80.00 $0.00
25 mg $175.00 $0.00

Pricing updated 2015-09-03. Prices are subject to change without notice.

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Description
Synonyms
  • Palmitoyl Ceramide

Ceramides are generated from sphingomyelin through activation of sphingomyelinases or through the de novo synthesis pathway, which requires coordinate action of serine palmitoyl transferase and ceramide synthase. They have been shown to mediate antiproliferative responses such as apoptosis, growth arrest, differentiation, and senescence.1 C-16 ceramide is an endogenous ceramide, generated by ceramide synthase 6 (CerS6), that acts a lipid second messenger to regulate apoptosis and stress signaling.2 Accumulation of C-16 ceramide through PPMP (30 μM) or MAPP (50 μM) treatment or from addition of 100 μM synthetic C-16 ceramide induces apoptosis in neutrophil cultures via caspase-3 activation.3

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Technical Information
Formal Name N-​[2R-​hydroxy-​1S-​(hydroxymethyl)-​3E-​heptadecen-​1-​yl]-​hexadecanamide
CAS Number 24696-26-2
Synonyms
  • Palmitoyl Ceramide
Molecular Formula C34H67NO3
Formula Weight 537.9
Purity ≥98%
Formulation A crystalline solid
SMILES CCCCCCCCCCCCC/C=C/[C@@H]​(O)​[C@@H]​(NC(CCCCCCCCCCCCCCC)​=O)​CO
InChI Code ​1S/C34H67NO3/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-33(37)​32(31-36)​35-34(38)​30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h27,29,32-33,36-37H,3-26,28,30-31H2,1-2H3,(H,35,38)​/b29-27+/t32-,33+/m0/s1
InChI Key YDNKGFDKKRUKPY-TURZORIXSA-N

WARNING - This product is not for human or veterinary use.

Shipping & Storage
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
Stability 2 years
Product Downloads & Resources
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Download Product Insert 139 Kb PDF

Download Safety Data Sheet (SDS) 27 Kb PDF

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Additional Information

View the Cayman Structure Database for chemical structure definitions for many Cayman products

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References & Background Reading
Product Description References

1. Ogretmen, B., Pettus, B.J., Rossi, M.J., et al. Biochemical mechanisms of the generation of endogenous long chain ceramide in response to exogenous short chain ceramide in the A547 human lung adenocarcinoma cell line. J Biol Chem 277(15) 12960-9 (2002).

2. White-Gilbertson, S., Mullen, T., Senkal, C., et al. Ceramide synthase 6 modulates TRAIL sensitivity and nuclear translocation of active caspase 3 in colon cancer cells. Oncogene 28(8) 1132-1141 (2009).

3. Seumois, G., Fillet, M., Gillet, L., et al. De novo C16- and C24-ceramide generation contributes to spontaneous neutrophil apoptosis. J Leukoc Biol 81 1477-86 (2007).

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