A cell-permeable analog of naturally occurring ceramides
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Labeled Version(s)
24826C6 Ceramide-d7 (d18:1-d7/6:0)
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C6 Ceramide (d18:1/6:0)

Item No. 62525

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-hexanamide
CAS Number
124753-97-5
Synonyms
  • N-Caproyl-C18-sphingosine
  • Cer(18:1/6:0)
  • Ceramide (d18:1/6:0)
  • C6 Ceramide
  • N-hexanoyl-D-erythro-sphingosine
Molecular Formula
C24H47NO3
Formula Weight
397.6
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 22 mg/mlDMSO: 20 mg/mlEthanol: 33 mg/mlEthanol:PBS (pH 7.2) 1:1: .5 mg/ml
SMILES
CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](NC(CCCCC)=O)CO
InChi Code
InChI=1S/C24H47NO3/c1-3-5-7-8-9-10-11-12-13-14-15-16-18-19-23(27)22(21-26)25-24(28)20-17-6-4-2/h18-19,22-23,26-27H,3-17,20-21H2,1-2H3,(H,25,28)/b19-18+/t22-,23+/m0/s1
InChi Key
NPRJSFWNFTXXQC-QFWQFVLDSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    C6 ceramide is a cell-permeable analog of naturally occurring ceramides. With a longer carbon chain than C2 ceramide, it is somewhat more hydrophobic, and may more closely mimic the effects of natural ceramides.1 C6 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 C6 ceramide acts in neuronal axons to inhibit neurite growth.7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Dobrowsky, R.T., and Hannun, Y.A. Ceramide stimulates a cytosolic protein phosphatase. The Journal of Biological Chemisty 267(8), 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. The Journal of Biological Chemisty 272(11), 6918-6926 (1997).

    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. 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(6), 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. The Journal of Biological Chemisty 271(32), 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. The Journal of Biological Chemisty 272(4), 2038-3035 (1997).