Sphingolipid pathway intermediate
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Labeled Version(s)
27145Sphinganine-d7 (d18:0)
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Sphinganine (d18:0)

Item No. 10007945

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2S-amino-1,3R-octadecanediol
CAS Number
764-22-7
Synonyms
  • Dihydrosphingosine
  • D-erythro-Dihydrosphingosine
  • Dihydro-D-erythro Sphingosine
  • Sphinganine
  • D-erythro-Sphinganine
Molecular Formula
C18H39NO2
Formula Weight
301.5
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 2 mg/mlEthanol: Miscible
SMILES
OC[C@H](N)[C@H](O)CCCCCCCCCCCCCCC
InChi Code
InChI=1S/C18H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17-18,20-21H,2-16,19H2,1H3/t17-,18+/m0/s1
InChi Key
OTKJDMGTUTTYMP-ZWKOTPCHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    5 mg

    $49

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    10 mg

    $93

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    25 mg

    $184

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    50 mg

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    Product Description

    Sphinganine (d18:0) is a precursor of ceramide and sphingosine as well as a substrate of sphingosine kinases, which generate sphinganine-1-phosphate. Sphinganine levels increase significantly in response to certain mycotoxins, including fumonisins,1,2 as well as in some cancers.3 Sphinganine can block protein kinase C activation in some cases but not others.4,5 Sphinganine-1-phosphate can emulate sphingosine-1-phosphate in cell signaling or have opposite intracellular effects.6,7,8

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Pruett, S.T., Bushnev, A., Hagedorn, K., et al. Biodiversity of sphingoid bases ("sphingosines") and related amino alcohols. J. Lipid Res. 49(8), 1621-1639 (2008).

    2. Shephard, G.S., van der Westhuizen, L., and Sewram, V. Biomarkers of exposure to fumonisin mycotoxins: A review. Food Addit. Contam. 24(10), 1196-1201 (2007).

    3. Yin, J., Miyazaki, K., Shaner, R.L., et al. Altered sphingolipid metabolism induced by tumor hypoxia - new vistas in glycolipid tumor markers. FEBS Lett. 584(9), 1872-1878 (2010).

    4. Merrill, A.H., Jr., Sereni, A.M., Stevens, V.L., et al. Inhibition of phorbol ester-dependent differentiation of human promyelocytic leukemic (HL-60) cells by sphinganine and other long-chain bases. The Journal of Biological Chemisty 261(27), 12610-12615 (1986).

    5. Merrill, A.H., Jr., Nimkar, S., Menaldino, D., et al. Structural requirements for long-chain (shingoid) base inhibition of protein kinase C in vitro and for the cellular effects of these compounds. Biochemistry 28(8), 3138-3145 (1989).

    6. Coste, O., Brenneis, C., Linke, B., et al. Sphingosine 1-phosphate modulates spinal nociceptive processing. The Journal of Biological Chemisty 283(47), 32442-32451 (2008).

    7. Bu, S., Yamanaka, M., Pei, H., et al. Dihydrosphingosine 1-phosphate stimulates MMP1 gene expression via activation of ERK1/2-Ets1 pathway in human fibroblasts. FASEB J. 20(1), 184-186 (2006).

    8. Bu, S., Kapanadze, B., Hsu, T., et al. Opposite effects of dihydrosphingosine 1-phosphate and sphingosine 1-phosphate on transforming growth factor-β/Smad signaling are mediated through the PTEN/PPM1A-dependent pathway. The Journal of Biological Chemisty 283(28), 19593-19602 (2008).