A bioactive sphingolipid
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C4 Ceramide (d18:1/4:0)

Item No. 22528

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-butanamide
CAS Number
74713-58-9
Synonyms
  • Cer(d18:1/4:0)
  • Ceramide (d18:1/4:0)
  • N-butyroyl-D-erythro-Sphingosine
Molecular Formula
C22H43NO3
Formula Weight
369.6
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): <50 µg/ml
SMILES
OC[C@H](NC(CCC)=O)[C@H](O)/C=C/CCCCCCCCCCCCC
InChi Code
InChI=1S/C22H43NO3/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-18-21(25)20(19-24)23-22(26)17-4-2/h16,18,20-21,24-25H,3-15,17,19H2,1-2H3,(H,23,26)/b18-16+/t20-,21+/m0/s1
InChi Key
UCBLGIBMIAFISC-CQLAPORSSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    10 mg

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    100 mg

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    250 mg

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    Product Description

    C4 Ceramide is a bioactive sphingolipid and cell-permeable analog of naturally occurring ceramides.1,2,3 It inhibits IL-4 production by 16% in EL4 T cells stimulated with phorbol 12-myristate 13-acetate (PMA; Item No. 10008014) when used at a concentration of 10 μM.1 C4 Ceramide is cytotoxic to SK-BR-3 and MCF-7/Adr breast cancer cells (IC50s = 15.9 and 19.9 μM, respectively).2 C4 Ceramide also increases maturation and stability of cystic fibrosis transmembrane conductance regulator (CFTR) proteins bearing the F508 deletion (F508del) mutation, enhances cAMP-activated chloride secretion, and suppresses secretion of IL-8 in primary epithelial cells isolated from patients with cystic fibrosis.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Park, J., Li, Q., Chang, Y.T., et al. Inhibitory activity of a ceramide library in interleukin-4 production from activated T cells. Bioorg. Med. Chem. 13(7), 2589-2595 (2005).

    2. Crawford, K.W., Bittman, R., Chun, J., et al. Novel ceramide analogues display selective cytotoxicity in drug-resistant breast tumor cell lines compared to normal breast epithelial cells. Cell Mol. Biol. (Noisy-le-grand) 49(7), 1017-1023 (2003).

    3. Caohuy, H., Yang, Q., Eudy, Y., et al. Activation of 3-phosphoinositide-dependent kinase 1 (PDK1) and serum- and glucocorticoid-induced protein kinase 1 (SGK1) by short-chain sphingolipid C4-ceramide rescues the trafficking defect of ΔF508-cystic fibrosis transmembrane conductance regulator (ΔF508-CFTR). The Journal of Biological Chemisty 289(52), 35953-35968 (2014).