A cell-permeable ceramide analog
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Product Categories

Product Type

Biochemicals
Lipids
Sphingolipids

Research Area

Lipid Biochemistry
Sphingolipids

C8 Ceramide (d18:1/8:0)

Item No. 62540

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-octanamide
CAS Number
74713-59-0
Synonyms
  • C8 Ceramide
  • Cer(d18:1/8:0)
  • N-octanoyl-D-erythro-Sphingosine
  • N-Octanoylsphingosine
Molecular Formula
C26H51NO3
Formula Weight
425.7
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
acidic PBS: <50 µg/mlbasic PBS: <50 µg/mlDMF: >22 mg/mlDMSO: >20 mg/mlEthanol: >33 mg/mlPBS pH 7.2: <50 µg/ml
SMILES
CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](NC(CCCCCCC)=O)CO
InChi Code
InChI=1S/C26H51NO3/c1-3-5-7-9-10-11-12-13-14-15-16-18-19-21-25(29)24(23-28)27-26(30)22-20-17-8-6-4-2/h19,21,24-25,28-29H,3-18,20,22-23H2,1-2H3,(H,27,30)/b21-19+/t24-,25+/m0/s1
InChi Key
APDLCSPGWPLYEQ-WRBRXSDHSA-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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    10 mg

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    25 mg

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    Product Description

    C8 Ceramide (d18:1/8:0) is a cell-permeable analog of naturally occurring ceramides. Unlike C2 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 C8 Ceramide (d18:1/8:0) may more closely mimic the effects of ceramide elevation than does treatment with shorter chain ceramide analogs. C8 Ceramide (d18:1/8:0) 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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    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(2), 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).