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C2 Ceramide (d18:1/2:0)

Item № 62510
CAS № 3102-57-6
Purity ≥98%
product image
                (CAS 3102-57-6)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     1 mg $10.00 0.00
     5 mg $45.00 0.00
     10 mg $80.00 0.00
     25 mg $175.00 0.00

Pricing updated 2019-04-24. Prices are subject to change without notice.

Description
Synonyms
  • C2 Ceramide
  • Ceramide (d18:1/2:0)
  • Cer(18:1/2:0)
  • N-acetoyl-D-erythro-sphingosine

C2 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 C2 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 C2 ceramide to destabilize membranes may be responsible for its inhibition of platelet aggregation.7

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Technical Information
Formal Name
N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-acetamide
CAS Number
3102-57-6
Synonyms
  • C2 Ceramide
  • Ceramide (d18:1/2:0)
  • Cer(18:1/2:0)
  • N-acetoyl-D-erythro-sphingosine
Molecular Formula
C20H39NO3
Formula Weight
341.5
Purity
≥98%
Formulation
A crystalline solid
SMILES
CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](NC(C)=O)CO
InChI Code
InChI=1S/C20H39NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20(24)19(17-22)21-18(2)23/h15-16,19-20,22,24H,3-14,17H2,1-2H3,(H,21,23)/b16-15+/t19-,20+/m0/s1
InChI Key
BLTCBVOJNNKFKC-QUDYQQOWSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Stability
≥ 1 year
Downloads & Resources
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Additional Information

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References & Product Citations
Product Description References

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 The Journal of Biological Chemisty 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(21), 15523-15530 (1993).

4. Gudz, T.I., Tserng, K.Y., and Hoppel, C.L. Direct inhibition of mitochondrial respiratory chain complex III by cell-permeable ceramide J. Biol. Chem. 272(39), 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 The Journal of Biological Chemisty 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(32), 19251-19255 (1996).

7. Simon, C.G., Jr., 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).

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