A cell-permeable analog of naturally occurring ceramides
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C2 Ceramide (d18:1/2:0)

Item No. 62510

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
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 (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: >22 mg/ml (from C-8 Ceramide)DMSO: >20 mg/ml (from C-8 Ceramide)Ethanol: >33 mg/ml (from C-8 Ceramide)PBS pH 7.2: <50 µg/ml (from C-8 Ceramide)
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    5 mg

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    10 mg

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    25 mg

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    Product Description

    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

    WARNING This product is not for human or veterinary use.

    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. The Journal of Biological Chemisty 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. The Journal of Biological Chemisty 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. The Journal of Biological Chemisty 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).