A pharmacological tool to probe the activity of protein kinase C
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Sphingosine (d18:1)

Item No. 10007907

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2S-amino-4E-octadecene-1,3R-diol
CAS Number
123-78-4
Synonyms
  • (−)-Sphingosine
  • D-erythro-Sphingosine C-18
Molecular Formula
C18H37NO2
Formula Weight
299.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 1 mg/mlEthanol: Miscible
SMILES
OC[C@H](N)[C@H](O)/C=C/CCCCCCCCCCCCC
InChi Code
InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m0/s1
InChi Key
WWUZIQQURGPMPG-KRWOKUGFSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

    $45

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    25 mg

    $79

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    50 mg

    $135

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    100 mg

    $203

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    Product Description

    Sphingosine (d18:1) is formed primarily from the breakdown of ceramide.1 Sphingosine inhibits protein kinase C and phosphatidic acid phosphohydrolase, whereas it activates phospholipase D and diacylglycerol (DAG) kinase.1 Phosphorylation of sphingosine by sphingosine kinases 1 and 2 (SPHK 1, SPHK 2) produces sphingosine-1-phosphate, a potent bioactive lipid that exhibits a broad spectrum of biological activities including cell proliferation, survival, migration, cytoskeletal organization, and morphogenesis.2,3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hannun, Y.A., Luberto, C., and Argraves, K.M. Enzymes of sphingolipid metabolism: From modular to integrative signaling. Biochemistry 40(16), 4893-4903 (2001).

    2. Takuwa, Y., Takuwa, N., and Sugimoto, N. The Edg family G protein-coupled receptors for lysophospholipids: Their signaling properties and biological activities. J. Biochem. 131(6), 767-771 (2002).

    3. Ishii, I., Fukushima, N., Ye, X., et al. Lysophospholipid receptors: Signaling and biology. Annu. Rev. Biochem. 73, 321-354 (2004).

    4. Kluk, M.J., and Hla, T. Signaling of sphingosine-1-phosphate via the S1P/EDG-family of G-protein-coupled receptors. Biochim. Biophys. Acta 1582(1-3), 72-80 (2002).