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C-2 Ceramide

Cayman Chemical Item Number 62510

N-Acetylsphingosine (CAS 3102-57-6)

C-2 Ceramide (CAS 3102-57-6)

See more	Ceramides/Sphingolipids (58)

Description

C-2 ceramide is a cell-permeable analog of naturally occurring ceramides. It mediates many diverse biological activities, as do natural ceramides. These processes include differentiation of HL-60 cells,¹ induction of apoptosis,² activation of protein phosphatase 2A,³ and inhibition of the mitochondrial respiratory chain.⁴ C-2 ceramide also enhances the expression of COX-2 in human dermal fibroblasts⁵ and stimulates the growth of bovine aortic smooth muscle cells.⁶ The ability of C-2 ceramide to destabilize membranes may be responsible for its inhibition of platelet aggregation.⁷

1 Okazaki, T., Bielawska, A., Bell, R.M., et al. Role of ceramide as a lipid mediator of 1α,25-dihydroxyvitamin D₃-induced HL-60 cell differentiation. J Biol Chem 265 15823-15831 (1990).

2 Obeid, L.M., Linardic, C.M., Karolak, L.A., et al. Programmed cell death induced by ceramide. Science 259 1769-1771 (1993).

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 Ballou, L.R., Chao, C.P., Holness, M.A., et al. Interleukin-1-mediated PGE₂ production and sphingomyelin metabolism. Evidence for the regulation of cyclooxygenase gene expression by sphingosine and ceramide. J Biol Chem 267 20044-20050 (1992).

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 Simon, C.G., and Gear, A.R.L. Membrane-destabilizing properties of C₂-ceramide may be responsible for its ability to inhibit platelet aggregation. Biochemistry 37 2059-2069 (1998).

Synonyms	N-Acetylsphingosine
Formal Name	N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-acetamide
CAS Number	3102-57-6
Molecular Formula	C₂₀H₃₉NO₃
Formula Weight	341.5
Formulation	A crystalline solid
Purity	>98%
Stability	1 year
Storage	-20°C
Shipping	Room temperature in continental US; may vary elsewhere
SMILES	Copy SMILES to clipboard CCCCCCCCCCCCC/C=C/C(O)[C@H](CO)NC(=O)C

Background Reading

Obeid, L.M., Linardic, C.M., Karolak, L.A., et al. Programmed cell death induced by ceramide. Science 259 1769-1771 (1993).

Ballou, L.R., Chao, C.P., Holness, M.A., et al. Interleukin-1-mediated PGE₂ production and sphingomyelin metabolism. Evidence for the regulation of cyclooxygenase gene expression by sphingosine and ceramide. J Biol Chem 267 20044-20050 (1992).

Okazaki, T., Bielawska, A., Bell, R.M., et al. Role of ceramide as a lipid mediator of 1α,25-dihydroxyvitamin D₃-induced HL-60 cell differentiation. J Biol Chem 265 15823-15831 (1990).

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

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).

Simon, C.G., and Gear, A.R.L. Membrane-destabilizing properties of C₂-ceramide may be responsible for its ability to inhibit platelet aggregation. Biochemistry 37 2059-2069 (1998).

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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C-2 Ceramide is available in the following screening library:

Bio-active Lipid I Screening Library (96-Well)

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

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.

Related Products

AV-Ceramide Exclusive

N,N-Dimethylsphingosine

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