A bioactive sphingolipid
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Sphinganine-1-phosphate (d18:0)

Item No. 22500

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2(S)-amino-1,3(R)-octadecanediol, 1-(dihydrogen phosphate)
CAS Number
19794-97-9
Synonyms
  • C18-dihydro Sphingosine-1-phosphate
  • D-erythro-Sphinganine-1-phosphate
  • dihydro-D-erythro-Sphingosine-1-phosphate
Molecular Formula
C18H40NO5P
Formula Weight
381.5
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
0.3 M NaOH: 4 mg/mlDMF: <50 µg/mlDMSO: <50 µg/mlEthanol: <50 µg/mlPBS (pH 7.2): <50 µg/ml
SMILES
N[C@H]([C@H](O)CCCCCCCCCCCCCCC)COP(O)(O)=O
InChi Code
InChI=1S/C18H40NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(20)17(19)16-24-25(21,22)23/h17-18,20H,2-16,19H2,1H3,(H2,21,22,23)/t17-,18+/m0/s1
InChi Key
YHEDRJPUIRMZMP-ZWKOTPCHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

    $69

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    1 mg

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    5 mg

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    Product Description

    Sphinganine-1-phosphate is an intermediate in the metabolism of glycosphingolipids and sphingolipids. It acts as an antagonist at the sphingosine-1-phosphate (S1P1/EDG-1) receptor (Ki = 15 nM).1 Sphinganine-1-phosphate prevents liver and kidney damage following hepatic ischemia and reperfusion injury in mice at doses lower than 0.1 and 0.2 mg/kg when administered prior to or following reperfusion, respectively.2 It has antifibrotic effects in scleroderma fibroblasts through normalization of PTEN protein levels, collagen and matrix metalloproteinase-1 (MMP-1) expression, and Smad3 phosphorylation.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Van Brocklyn, J.R., Lee, M.-J., Menzeleev, R., et al. Dual actions of sphingosine-1-phosphate: extracellular through the Gi-coupled receptor Edg-1 and intracellular to regulate proliferation and survival. J. Cell. Biol. 142(1), 229-240 (1998).

    2. Park, S.W., Kim, M., Chen, S.W.C., et al. Sphinganine-1-phosphate attenuates both hepatic and renal injury induced by hepatic ischemia and reperfusion in mice. Shock 33(1), 31-42 (2010).

    3. Bu, S., Asano, Y., Bujor, A., et al. Dihydrosphingosine 1-phosphate has a potent antifibrotic effect in scleroderma fibroblasts via normalization of phosphatase and tensin homolog levels. Arthrtis Rheum. 62(7), 2117-2126 (2010).

    4. 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).

    Product Citations

    Lahey, L.J., Mardjuki, R.E., Wen, X., et al. LRRC8A:C/E heteromeric channels are ubiquitous transporters of cGAMP. Mol. Cell. 80(4), 578-591 (2020).