A mixture of bioactive sphingolipids
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D-erythro/L-threo Lysosphingomyelin (d18:1)

Item No. 31557

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[[[(2-amino-3-hydroxy-4-octadecen-1-yl)oxy]hydroxyphosphinyl]oxy]-N,N,N-trimethyl-ethanaminium, inner salt
CAS Number
82970-80-7
Synonyms
  • D-erythro/L-threo Lyso SM(18:1)
  • D-erythro/L-threo Sphingosine-1-Phosphocholine (d18:1)
  • D-erythro/L-threo-Sphingosylphosphorylcholine
Molecular Formula
C23H49N2O5P
Formula Weight
464.6
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol (2:1): soluble
SMILES
NC(COP(OCC[N+](C)(C)C)([O-])=O)C(O)/C=C/CCCCCCCCCCCCC
InChi Code
InChI=1S/C23H49N2O5P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(26)22(24)21-30-31(27,28)29-20-19-25(2,3)4/h17-18,22-23,26H,5-16,19-21,24H2,1-4H3/b18-17+
InChi Key
JLVSPVFPBBFMBE-ISLYRVAYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $214

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    10 mg

    $356

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    50 mg

    $1,679

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    Product Description

    Lysosphingomyelin is an endogenous bioactive sphingolipid and a constituent of lipoproteins.1,2 It is produced by the removal of the acyl group from sphingomyelin by a deacylase and acts as a precursor in the biosynthesis of sphingosine-1-phosphate (S1P; Item No. 62570). D-erythro Lysosphingomyelin is an agonist of the S1P receptors S1P1, S1P2, and S1P3 (EC50s = 167.7, 368.1, and 482.6 nM, respectively, for the human receptors).3 It is also an agonist of the orphan receptor ovarian cancer G protein-coupled receptor 1 (ORG1) that induces calcium accumulation in cells overexpressing OGR1 (EC50 = ~35 nM).4 Levels of D-erythro lysosphingomyelin are increased in skin isolated from patients with atopic dermatitis, as well as postmortem brain from patients with Niemann-Pick disease type A, but not type B.2,5 L-threo lysosphingomyelin is also an S1P1-3 agonist (EC50s = 19.3, 131.8, and 313.3 nM, respectively).3 This product is a mixture of D-erythro and L-threo lysosphingomyelin. As this product is derived from a natural source, there may be variations in the sphingoid backbone. [Matreya, LLC. Catalog No. 1321]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ito, M., Kurita, T., and Kita, K. A novel enzyme that cleaves the N-acyl linkage of ceramides in various glycosphingolipids as well as sphingomyelin to produce their lyso forms. The Journal of Biological Chemisty 270(41), 24370-24374 (1995).

    2. Nixon, G.F., Mathieson, F.A., and Hunter, I. The multi-functional role of sphingosylphosphorylcholine. Prog. Lipid Res. 47(1), 62-75 (2008).

    3. Im, D.-S., Clemens, J., Macdonald, T.L., et al. Characterization of the human and mouse sphingosine 1-phosphate receptor, S1P5 (Edg-8): Structure-activity relationship of sphingosine1-phosphate receptors. Biochemistry 40(46), 14053-14060 (2001).

    4. Meyer zu Heringdorf, D., Himmel, H.M., and Jakobs, K.H. Sphingosylphosphorylcholine-biological functions and mechanisms of action. Biochim. Biophys. Acta 1582(1-3), 178-189 (2002).

    5. Rodriguez-Lafrasse, C., and Vanier, M.T. Sphingosylphosphorylcholine in Niemann-Pick disease brain: Accumulation in type A but not in type B. Neurochem. Res. 24(2), 199-205 (1999).