A bioactive sphingolipid
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C6 L-threo Ceramide (d18:1/6:0)

Item No. 24390

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(1S,2S,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-hexanamide
CAS Number
189894-80-2
Synonyms
  • L-threo Cer(d18:1/6:0)
  • L-threo Ceramide (d18:1/6:0)
  • N-hexanoyl-L-threo-Sphingosine
Molecular Formula
C24H47NO3
Formula Weight
397.6
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: SolubleDMF: 5 mg/mlDMSO: SolubleEthanol: Soluble
SMILES
OC[C@@H]([C@@H](O)/C=C/CCCCCCCCCCCCC)NC(CCCCC)=O
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-WBJAFTEYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    1 mg

    $256

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    Product Description

    C6 L-threo Ceramide is a bioactive sphingolipid and cell-permeable analog of naturally occurring ceramides.1,2 C6 L-threo Ceramide is cytotoxic to U937 cells in vitro (IC50 = 18 μM).3 It is metabolically inactive and, unlike C6 L-erythro ceramide (Item No. 24388), C6 L-threo ceramide cannot be converted to C6 glucosylceramide by ceramide glucosyltransferase.2 C6 L-threo Ceramide enhances IL-4 production induced by phorbol 12-myristate 13-acetate (PMA; Item No. 10008014) in EL4 T cells when used at a concentration of 10 μM.4 [Matreya, LLC. Catalog No. 1828]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Schwarz, A., and Futerman, A.H. Distinct roles for ceramide and glucosylceramide at different stages of neuronal growth. J. Neurosci. 17(9), 2929-2938 (1997).

    2. Paul, P., Kamisaka, Y., Marks, D.L., et al. Purification and characterization of UDP-glucose: Ceramide glucosyltransferase from rat liver Golgi membranes. The Journal of Biological Chemisty 271(4), 2287-2293 (1996).

    3. 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).

    4. 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).