Sphingosine-1-Phosphate

Cayman Chemical Item Number 62570

S1P; Sphingosine-1-Phosphoric Acid (CAS 26993-30-6)

Sphingosine-1-Phosphate (CAS 26993-30-6)

Description

Sphingosine-1-phosphate (S1P) is the product of phosphorylation of sphingosine by sphingosine kinase. Like many products of sphingomyelin, it exhibits a wide range of biological activities. Not only does it enhance cell growth,¹ but it can inhibit the normal apoptotic response to a variety of stimuli.² The ability of PKC to block apoptosis is likely due to the formation of S1P. S1P stimulates MAPK and counteracts the ceramide-induced activation of SAPK and JNK.² It also increases intracellular calcium levels by both the liberation of calcium from internal stores³ and through activation of a Gi protein-coupled receptor resulting in the opening of a cell surface calcium channel.⁴

1 Olivera, A., and Spiegel, S. Sphingosine-1-phosphate as second messenger in cell proliferation induced by PDGF and FCS mitogens. Nature 365 557-560 (1993).

2 Cuvillier, O., Pirianov, G., Kleuser, B., et al. Suppression of ceramide-mediated programmed cell death by sphingosine-1-phosphate. Nature 381 800-803 (1996).

3 Mattie, M., Brooker, G., and Spiegel, S. Sphingosine-1-phosphate, a putative second messenger, mobilizes calcium from internal stores via an inositol trisphosphate-independent pathway. J Biol Chem 269 3181-3188 (1994).

4 van Koppen, C.J., zu Heringdorf, D.M., Laser, K.T., et al. Activation of a high affinity Gi protein-coupled plasma membrane receptor by sphingosine-1-phosphate. J Biol Chem 271 2082-2087 (1996).

Synonyms

S1P
Sphingosine-1-Phosphoric Acid

Formal Name

2S-amino-1-(dihydrogen phosphate)-4E-octadecene-1,3R-diol

CAS Number

26993-30-6

Molecular Formula

C₁₈H₃₈NO₅P

Formula Weight

379.5

Formulation

A crystalline solid

Purity

≥98%

Stability

1 year

Storage

-20°C

Shipping

Room temperature in continental US; may vary elsewhere

SMILES

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CCCCCCCCCCCCC/C=C/C(O)[C@@H](N)COP(=O)(O)O

Background Reading

Olivera, A., and Spiegel, S. Sphingosine-1-phosphate as second messenger in cell proliferation induced by PDGF and FCS mitogens. Nature 365 557-560 (1993).

van Koppen, C.J., zu Heringdorf, D.M., Laser, K.T., et al. Activation of a high affinity Gi protein-coupled plasma membrane receptor by sphingosine-1-phosphate. J Biol Chem 271 2082-2087 (1996).

Cuvillier, O., Pirianov, G., Kleuser, B., et al. Suppression of ceramide-mediated programmed cell death by sphingosine-1-phosphate. Nature 381 800-803 (1996).

Mattie, M., Brooker, G., and Spiegel, S. Sphingosine-1-phosphate, a putative second messenger, mobilizes calcium from internal stores via an inositol trisphosphate-independent pathway. J Biol Chem 269 3181-3188 (1994).

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1 mg 
$75.00

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5 mg 
$281.00

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10 mg 
$450.00

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25 mg 
$844.00

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Sphingosine-1-Phosphate (CAS 26993-30-6)

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Sphingosine-1-Phosphate

Sphingosine-1-Phosphate (CAS 26993-30-6)

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