An internal standard for the quantification of S1P
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Unlabeled Version(s)
62570Sphingosine-1-phosphate (d18:1)
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Sphingosine-1-phosphate-d7 (d18:1)

Item No. 10008121

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S,3R,4E)-2-amino-4-octadecene-16,16,17,17,18,18,18-d7-1,3-diol, 1-(dihydrogen phosphate)
CAS Number
2260670-15-1
Synonyms
  • S1P-d7 (d18:1)
  • Sphingosine-1-Phosphoric Acid-d7
Molecular Formula
C18H31D7NO5P
Formula Weight
386.5
Purity
≥99% deuterated forms (d1-d7)
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
0.3 M NaOH: 4 mg/ml
SMILES
O[C@H](/C=C/CCCCCCCCCCC([2H])([2H])C([2H])([2H])C([2H])([2H])[2H])[C@@H](N)COP(O)(O)=O
InChi Code
InChI=1S/C18H38NO5P/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/h14-15,17-18,20H,2-13,16,19H2,1H3,(H2,21,22,23)/b15-14+/t17-,18+/m0/s1/i1D3,2D2,3D2
InChi Key
DUYSYHSSBDVJSM-AVMMVCTPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $401

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    1 mg

    $720

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    Product Description

    Sphingosine-1-phosphate-d7 is intended for use as an internal standard for the quantification of sphingosine-1-phosphate (S1P; Item No. 62570) by GC- or LC-MS. S1P is the product of phosphorylation of sphingosine by sphingosine kinase that is secreted from cells and acts as an agonist at S1P receptors.1 It increases intracellular calcium levels in TAg-Jurkat cells expressing S1P1 and Gqi5, which allows for phospholipase C stimulation by Gi proteins, when used at a concentration of 200 nM, as well as in TAg-Jurkat cells expressing S1P2 and S1P3 receptors (EC50s = 8 and 11 nM, respectively).2 Intra- and extracellular levels of S1P vary spatially allowing it to function as an autocrine or paracrine factor, respectively, and dysregulation of S1P levels are associated with various disease states, such as inflammation and autoimmunity.3 S1P has a wide variety of effects, including an involvement in cell growth, angiogenesis, immunity, and neuroprotection.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sanchez, T., and Hla, T. Structural and functional characteristics of S1P receptors. J. Cell. Biochem. 92(5), 913-922 (2004).

    2. An, S., Bleu, T., and Zheng, Y. Transduction of intracellular calcium signals through G protein-mediated activation of phospholipase C by recombinant sphingosine 1-phosphate receptors. Mol. Pharmacol. 55(5), 787-794 (1999).

    3. Cartier, A., and Hla, T. Sphingosine 1-phosphate: Lipid signaling in pathology and therapy. Science 366(6463), (2019).