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C-6 Ceramide

Cayman Chemical Item Number 62525

N-Caproyl-C18-sphingosine; N-Hexanoylsphingosine (CAS 124753-97-5)

C-6 Ceramide (CAS 124753-97-5)

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Description

C-6 ceramide is a cell-permeable analog of naturally occurring ceramides. With a longer carbon chain than C-2 ceramide, it is somewhat more hydrophobic, and may more closely mimic the effects of natural ceramides.1 C-6 ceramide mediates many diverse biological activities including apoptosis,2 activation of protein phosphatase 2A,1,3 and inhibition of the mitochondrial respiratory chain.4 It also enhances the expression of COX-2 in rat granulosa cells5 and stimulates the growth of bovine aortic smooth muscle cells.6 C-6 ceramide acts in neuronal axons to inhibit neurite growth.7

1 Dobrowsky, R.T., and Hannun, Y.A. Ceramide stimulates a cytosolic protein phosphatase. J Biol Chem 267 5048-5051 (1992).

2 Cai, Z., Bettaieb, A., El Mahdani, N., et al. Alteration of the sphingomyelin/ceramide pathway is associated with resistance of human breast carcinoma MCF7 cells to tumor necrosis factor-α-mediated cytotoxicity. J Biol Chem 272 6918-6926 (1997).

3 Dobrowsky, R.T., Kamibayashi, C., Mumby, M.C., et al. Ceramide activates heterotrimeric protein phosphatase 2A. J Biol Chem 268 15523-15530 (1993).

4 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).

5 Santana, P., Llanes, L., Hernandez, I., et al. Interleukin-1β stimulates sphingomyelin hydrolysis in cultured granulosa cells: Evidence for a regulatory role of ceramide on progesterone and prostaglandin biosynthesis. Endocrinology 137 2480-2489 (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 Posse de Chaves, E.I., Bussière, M., Vance, D.E., et al. Elevation of ceramide within distal neurites inhibits neurite growth in cultured rat sympathetic neurons. J Biol Chem 272 2038-3035 (1997).

Synonyms
  • N-Caproyl-C18-sphingosine
  • N-Hexanoylsphingosine
Formal Name N-​[(1S,​2R,​3E)-​2-​hydroxy-​1-​(hydroxymethyl)-​3-​heptadecen-​1-​yl]-​hexanamide
CAS Number 124753-97-5
Molecular Formula C24H47NO3
Formula Weight 397.6
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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CCCCCCCCCCCCC/C=C/C(O)​[C@H]​(CO)​NC(=O)​CCCCC

Background Reading

Dobrowsky, R.T., and Hannun, Y.A. Ceramide stimulates a cytosolic protein phosphatase. J Biol Chem 267 5048-5051 (1992).

Cai, Z., Bettaieb, A., El Mahdani, N., et al. Alteration of the sphingomyelin/ceramide pathway is associated with resistance of human breast carcinoma MCF7 cells to tumor necrosis factor-α-mediated cytotoxicity. J Biol Chem 272 6918-6926 (1997).

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).

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).

Dobrowsky, R.T., Kamibayashi, C., Mumby, M.C., et al. Ceramide activates heterotrimeric protein phosphatase 2A. J Biol Chem 268 15523-15530 (1993).

Posse de Chaves, E.I., Bussière, M., Vance, D.E., et al. Elevation of ceramide within distal neurites inhibits neurite growth in cultured rat sympathetic neurons. J Biol Chem 272 2038-3035 (1997).

Santana, P., Llanes, L., Hernandez, I., et al. Interleukin-1β stimulates sphingomyelin hydrolysis in cultured granulosa cells: Evidence for a regulatory role of ceramide on progesterone and prostaglandin biosynthesis. Endocrinology 137 2480-2489 (1996).

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C-6 Ceramide is available in the following screening library:

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
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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