C-16 Ceramide

Cayman Chemical Item Number 10681

Palmitoyl Ceramide (CAS 24696-26-2)

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Description

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

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).

Synonyms
  • Palmitoyl Ceramide
Formal Name N-​[2R-​hydroxy-​1S-​(hydroxymethyl)-​3E-​heptadecen-​1-​yl]-​hexadecanamide
CAS Number 24696-26-2
Molecular Formula C34H67NO3
Formula Weight 537.9
Formulation A crystalline solid
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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CCCCCCCCCCCCC/C=C/[C@@H]​(O)​[C@@H]​(NC(CCCCCCCCCCCCCCC)​=O)​CO
InCHI Code
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​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
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YDNKGFDKKRUKPY-TURZORIXSA-N

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Size Price Quantity Subtotal
1 mg $10.00 $0.00
5 mg $45.00 $0.00
10 mg $80.00 $0.00
25 mg $175.00 $0.00
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Ann Arbor, Michigan 48108 USA

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