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Nervonic Ceramide

Cayman Chemical Item Number 62530

C24 Ceramide; N-15Z-tetracosenoylsphingosine (CAS 54164-50-0)

Nervonic Ceramide (CAS 54164-50-0)

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Description

Production of ceramide occurs upon hydrolysis of sphingomyelin by a specific isoform of PLC, appropriately named sphingomyelinase.1 Nervonic ceramide (C24:1) is one of the most abundant naturally occurring ceramides.2,3,4 Ceramides mediate many diverse biological activities, as has been demonstrated in studies utilizing cell-permeable ceramide analogs. A few of the processes regulated by ceramides include apoptosis, cell differentiation,5 proliferation of smooth muscle cells,6 and inhibition of the mitochondrial respiratory chain.7

1 Perry, D.K., Obeid, L.M., and Hannun, Y.A. Ceramide and regulation of apoptosis and the stress response. Trends Cardiovasc Med 6 158-162 (1996).

2 Gu, Q., Kerwin, J.L., Watts, J.D., et al. Ceramide profiling of complex lipid mixtures by electrospray ionization mass spectrometry. Anal Biochem 244 347-356 (1997).

3 Clayton, R.B., Cooper, J.M., Curstedt, T., et al. Stimulation of erythroblast maturation in vitro by sphingolipids. J Lipid Res 15 557-562 (1974).

4 Krivit, W., and Hammarström, S. Identification and quantitation of free ceramides in human platelets. J Lipid Res 13 525-530 (1972).

5 Testi, R. Sphingomyelin breakdown and cell fate. Trends Biochem Sci 21 468-471 (1996).

6 Augé, N., Andrieu, N., Nègre-Salvayre, A., et al. The sphingomyelin-ceramide signaling pathway is involved in oxidized low density lipoprotein-induced cell proliferation. J Biol Chem 271 19251-19255 (1996).

7 Gudz, T.I., Tserng, K., and Hoppel, C.L. Direct inhibition of mitochondrial respiratory chain complex III by cell-permeable ceramide. J Biol Chem 272 24154-24158 (1997).

Synonyms
  • C24 Ceramide
  • N-15Z-tetracosenoylsphingosine
Formal Name N-​[(1S,​2R,​3E)-​2-​hydroxy-​1-​(hydroxymethyl)-​3-​heptadecen-​1-​yl]-​15Z-​tetracosenamide
CAS Number 54164-50-0
Molecular Formula C42H81NO3
Formula Weight 648.1
Formulation A crystalline solid
Purity >98%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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OC[C@H]​(NC(CCCCCCCCCCCCC/C=C\CCCCCCCC)​=O)​[C@H]​(O)​/C=C/CCCCCCCCCCCCC

Background Reading

Perry, D.K., Obeid, L.M., and Hannun, Y.A. Ceramide and regulation of apoptosis and the stress response. Trends Cardiovasc Med 6 158-162 (1996).

Augé, N., Andrieu, N., Nègre-Salvayre, A., et al. The sphingomyelin-ceramide signaling pathway is involved in oxidized low density lipoprotein-induced cell proliferation. J Biol Chem 271 19251-19255 (1996).

Gu, Q., Kerwin, J.L., Watts, J.D., et al. Ceramide profiling of complex lipid mixtures by electrospray ionization mass spectrometry. Anal Biochem 244 347-356 (1997).

Testi, R. Sphingomyelin breakdown and cell fate. Trends Biochem Sci 21 468-471 (1996).

Krivit, W., and Hammarström, S. Identification and quantitation of free ceramides in human platelets. J Lipid Res 13 525-530 (1972).

Clayton, R.B., Cooper, J.M., Curstedt, T., et al. Stimulation of erythroblast maturation in vitro by sphingolipids. J Lipid Res 15 557-562 (1974).

Gudz, T.I., Tserng, K., and Hoppel, C.L. Direct inhibition of mitochondrial respiratory chain complex III by cell-permeable ceramide. J Biol Chem 272 24154-24158 (1997).

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Nervonic Ceramide is available in the following screening library:

Size Price Quantity Subtotal
1 mg $18.00 $0.00
5 mg $81.00 $0.00
10 mg $144.00 $0.00
25 mg $315.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-05-26. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

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