A bioactive sphingolipid
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C8 D-threo Ceramide (d18:1/8:0)

Item No. 24391

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(1R,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-octanamide
CAS Number
175892-43-0
Synonyms
  • D-threo Cer(d18:1/8:0)
  • D-threo Ceramide (d18:1/8:0)
  • N-octanoyl-D-threo-Sphingosine
Molecular Formula
C26H51NO3
Formula Weight
425.7
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: SolubleDMF: SolubleDMSO: SolubleEthanol: Soluble
SMILES
OC[C@H]([C@H](O)/C=C/CCCCCCCCCCCCC)NC(CCCCCCC)=O
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-/m1/s1
InChi Key
APDLCSPGWPLYEQ-BKSWAVPISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $256

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    Product Description

    C8 D-threo Ceramide is a bioactive sphingolipid and cell-permeable analog of naturally occurring ceramides.1 It is cytotoxic to U937 cells (IC50 = 17 μM) and induces nuclear DNA fragmentation 5- to 6-fold more potently than C8 ceramide (Item No. 62540).1,2 C8 D-threo Ceramide is a substrate for E. coli diacylglycerol kinase.1 It activates ceramide-activated protein kinase (CAPK) in U937 cells. C8 D-threo Ceramide also enhances V. cholerae cytolysin pore formation in liposome lipid membranes, as measured by calcein release, with a 50% release dose (RD50) value of ~5 μg/ml.3 [Matreya, LLC. Catalog No. 1810]

    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. Chang, Y.-T., Choi, J., Ding, S., et al. The synthesis and biological characterization of a ceramide library. J. Am. Chem. Soc. 124(9), 1856-1857 (2002).

    3. Zitzer, A., Bittman, R., Verbicky, C.A., et al. Coupling of cholesterol and cone-shaped lipids in bilayers augments membrane permeabilization by the cholesterol-specific toxins streptolysin O and Vibrio cholerae cytolysin. The Journal of Biological Chemisty 276(18), 14628-14633 (2001).