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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

C-8 Ceramide

Cayman Chemical Item Number 62540

N-octanoylsphingosine (CAS 74713-59-0)

C-8 Ceramide (CAS 74713-59-0)

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Description

C-8 ceramide is a cell-permeable analog of naturally occurring ceramides. Unlike C-2 ceramide, it is metabolized within cells to generate natural ceramides, often causing a dramatic increase in cellular ceramide levels.1 For this reason, treatment of cells with C-8 ceramide may more closely mimic the effects of ceramide elevation than does treatment with shorter chain ceramide analogs. C-8 ceramide likely mediates many diverse biological activities, as do natural ceramides. It promotes the differentiation of human keratinocytes2 and induces apoptosis of both human leukemia cells and the U937 cell line.1,3

1 Karasavvas, N., Erukulla, R.K., Bittman, R., et al. Stereospecific induction of apoptosis in U937 cells by N-octanoyl-sphingosine stereoisomers and N-octyl-sphingosine. The ceramide amide group is not required for apoptosis. Eur J Biochem 236 729-737 (1996).

2 Wakita, H., Tokura, Y., Yagi, H., et al. Keratinocyte differentiation is induced by cell-permeant ceramides and its proliferation is promoted by sphingosine. Arch Dermatol Res 286 350-354 (1994).

3 Geley, S., Hartmann, B.L., and Kofler, R. Ceramides induce a form of apoptosis in human acute lymphoblastic leukemia cells that is inhibited by Bcl-2, but not by CrmA. FEBS Lett 400 15-18 (1997).

Synonyms
  • N-octanoylsphingosine
Formal Name N-​[(1S,​2R,​3E)-​2-​hydroxy-​1-​(hydroxymethyl)-​3-​heptadecen-​1-​yl]-​octanamide
CAS Number 74713-59-0
Molecular Formula C26H51NO3
Formula Weight 425.5
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)​CCCCCCC

Background Reading

Geley, S., Hartmann, B.L., and Kofler, R. Ceramides induce a form of apoptosis in human acute lymphoblastic leukemia cells that is inhibited by Bcl-2, but not by CrmA. FEBS Lett 400 15-18 (1997).

Karasavvas, N., Erukulla, R.K., Bittman, R., et al. Stereospecific induction of apoptosis in U937 cells by N-octanoyl-sphingosine stereoisomers and N-octyl-sphingosine. The ceramide amide group is not required for apoptosis. Eur J Biochem 236 729-737 (1996).

Wakita, H., Tokura, Y., Yagi, H., et al. Keratinocyte differentiation is induced by cell-permeant ceramides and its proliferation is promoted by sphingosine. Arch Dermatol Res 286 350-354 (1994).

C-8 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 2012-02-12. 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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