A bioactive sphingolipid
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C2 L-threo Ceramide (d18:1/2:0)

Item No. 24386

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(1S,2S,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-acetamide
CAS Number
143615-69-4
Synonyms
  • L-threo Cer(d18:1/2:0)
  • L-threo Ceramide (d18:1/2:0)
  • N-acetyl-L-threo-Sphingosine
Molecular Formula
C20H39NO3
Formula Weight
341.5
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: solubleDMF: 5 mg/mlDMSO: solubleEthanol: soluble
SMILES
CC(N[C@@H](CO)[C@@H](O)/C=C/CCCCCCCCCCCCC)=O
InChi Code
InChI=1S/C20H39NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20(24)19(17-22)21-18(2)23/h15-16,19-20,22,24H,3-14,17H2,1-2H3,(H,21,23)/b16-15+/t19-,20-/m0/s1
InChi Key
BLTCBVOJNNKFKC-LOVRKWTRSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $222

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    Product Description

    C2 L-threo Ceramide is a bioactive sphingolipid and cell-permeable analog of naturally occurring ceramides.1 It stimulates cholesterol efflux in CHO cells expressing the human ABCA1 receptor when used at a concentration of 10 μM, however, this efflux is 50% less than that stimulated by C2 ceramide (Item No. 62510). C2 L-threo Ceramide inhibits IL-4 production by 17% in EL4 T cells stimulated with phorbol 12-myristate 13-acetate (PMA; Item No. 10008014) when used at a concentration of 10 μM.2 It also induces cell cycle arrest in the G0/G1 phase and a 7-fold increase in sphingosine accumulation as well as inhibits growth of HL-60 leukemia cells.3,4 [Matreya, LLC. Catalog No. 1829]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ghering, A.B., and Davidson, W.S. Ceramide structural features required to stimulate ABCA1-mediated cholesterol efflux to apolipoprotein A-I. J. Lipid Res. 47(12), 2781-2788 (2006).

    2. 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).

    3. Baek, M.Y., Yoo, H.S., Nakaya, K., et al. Sphingolipid metabolic changes during chiral C2-ceramides induced apoptosis in human leukemia cells. Arch. Pharm. Res. 24(2), 144-149 (2001).

    4. Bielawska, A., Crane, H.M., Liotta, D., et al. Selectivity of ceramide-mediated biology. Lack of activity of erythro-dihydroceramide. The Journal of Biological Chemisty 268(35), 26226-26232 (1993).