C-20 Ceramide

Cayman Chemical Item Number 10724

(CAS 7344-02-7)

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Description

Ceramides are generated from sphingomyelin through activation of sphingomyelinases or through the de novo synthesis pathway. Certain forms of ceramide have been shown to mediate cellular responses such as apoptosis, growth arrest, and differentiation in certain cell types.1,2 C-20 Ceramide is a natural 20:0 ceramide that is abundant in the brain. It is synthesized de novo by ceramide synthases 1 and 2.3,4

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. Pandey, S., Murphy, R.F., and Agrawal, D.K. Recent advances in the immunobiology of ceramide. Exp Mol Pathol 82(3) 298-309 (2007).

3. Cowart, L.A. Sphingolipids: Players in the pathology of metabolic disease. Trends Endocrinol Metab 20(1) 34-42 (2008).

4. Pewzner-Jung, Y., Ben-Dor, S., and Futerman, A.H. When do lasses (longevity assurance genes) become CerS (ceramide synthases)? J Biol Chem 281(35) 25001-5 (2006).

Formal Name N-​[2R-​hydroxy-​1S-​(hydroxymethyl)-​3E-​heptadecen-​1-​yl]-​eicosanamide
CAS Number 7344-02-7
Molecular Formula C38H75NO3
Formula Weight 594.0
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(CCCCCCCCCCCCCCCCCCC)​=O)​CO
InCHI Code
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​1S/C38H75NO3/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-38(42)​39-36(35-40)​37(41)​33-31-29-27-25-23-21-16-14-12-10-8-6-4-2/h31,33,36-37,40-41H,3-30,32,34-35H2,1-2H3,(H,39,42)​/b33-31+/t36-,37+/m0/s1
InCHI Key
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XWBWIAOWSABHFI-NUKVNZTCSA-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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Cayman Chemical was formed over thirty years ago by demonstrating the value of naturally growing gorgonian corals as a renewable, economically viable source of prostaglandins. Today we operate our business knowing that we owe our start to the renewable resources our environment had provided. As Cayman Chemical continues to grow we consistently evaluate our business processes to ensure we are operating at the highest environmental standards.

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Ann Arbor, Michigan 48108 USA

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