A bioactive sphingolipid
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C2 Phytoceramide (t18:0/2:0)

Item No. 22823

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(1S,2S,3R)-2,3-dihydroxy-1-(hydroxymethyl)heptadecyl]-acetamide
CAS Number
21830-28-4
Synonyms
  • N-Acetyl Phytosphingosine
  • C2:0 Phytoceramide
  • Cer(t18:0/2:0)
  • Ceramide (t18:0/2:0)
  • NAPS
Molecular Formula
C20H41NO4
Formula Weight
359.6
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
OC[C@H](NC(C)=O)[C@@H]([C@@H](CCCCCCCCCCCCCC)O)O
InChi Code
InChI=1S/C20H41NO4/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-19(24)20(25)18(16-22)21-17(2)23/h18-20,22,24-25H,3-16H2,1-2H3,(H,21,23)/t18-,19+,20-/m0/s1
InChi Key
SZUJJDLBXJCDNT-ZCNNSNEGSA-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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    5 mg

    $236

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    Product Description

    C2 Phytoceramide is a bioactive semisynthetic sphingolipid that inhibits formyl peptide-induced oxidant release (IC50 = 0.38 µM) in suspended polymorphonuclear cells.1 It increases COX-2 protein levels 15-fold through ERK signaling.2 It induces death of keratinocytes (20% viability) with an ED50 value of 30 µM, the same concentration at which 35% of cells in a TUNEL assay are apoptotic. C2 Phytoceramide also has antiproliferative effects in CHO cells, with greater than 80% cytotoxicity achieved at a concentration of 20 µM, and induces internucleosomal DNA fragmentation.3 In addition, it inhibits the activation of phospholipase D (PLD) mediated by muscarinic acetylcholine receptors in vitro. [Matreya, LLC. Catalog No. 1897]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nakamura, T., Abe, A., Balazovich, K.J., et al. Ceramide regulates oxidant release in adherent human neutrophils. The Journal of Biological Chemisty 269(28), 18384-18389 (1994).

    2. Kim, H.J., Shin, W., Park, C.S., et al. Differential regulation of cyclooxygenase-2 expression by phytosphingosine derivatives, NAPS and TAPS, and its role in the NAPS or TAPS-mediated apoptosis. J. Invest. Dermatol. 121(5), 1126-1134 (2003).

    3. Lee, J.S., Min, D.S., Park, C., et al. Phytosphingosine and C2-phytoceramide induce cell death and inhibit carbachol-stimulated phospholipase D activation in Chinese hamster ovary cells expressing the Caenorhabditis elegans muscarinic acetylcholine receptor. FEBS. Lett. 499(1-2), 82-86 (2001).