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| Product Name | Sphingosine-1-phosphate, D-erythro |
| Description |
Signaling molecule |
| Purity | >98% |
| CAS No. | 26993-30-6 |
| Molecular Formula | C18H38NO5P |
| Molecular Weight | 379.5 |
| Field of Use | Not for use in humans. Not for use in diagnostics or therapeutics. For in vitro research use only. |
Properties
| Storage Temperature | -20ºC |
| Shipping Temperature | Shipped Ambient |
| Product Type | Second Messenger |
| Solubility | Sparingly soluble in 1:1 ethanol:water. Addition of small amounts of acetic acid may help dissolve this product. Soluble in warm methanol. |
| Source | Synthetic |
| Appearance | White solid |
| SMILES | [C@@H](N)([C@H](O)C=CCCCCCCCCCCCCC)CO[P](=O)(O)O |
| InChI | 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 |
| InChIKey | DUYSYHSSBDVJSM-KRWOKUGFSA-N |
| Safety Phrases |
Classification: Caution. Substance not yet fully tested. Safety Phrases: S22 - Do not breathe dust S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection S24/25 - Avoid contact with skin and eyes Hazard Phrases: H315 - Causes skin irritation. H319 - Causes serious eye irritation. H335 - May cause respiratory irritation. Precautionary Phrases: P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P280 Wear protective gloves/protective clothing/eye protection/face protection. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing P321 Specific treatment (see on this label). P405 Store locked up. P501 Dispose of contents/container in accordance with local/regional/national/international regulations |
| Cite This Product | Sphingosine-1-phosphate, D-erythro (StressMarq Biosciences Inc., Victoria BC CANADA, Catalog # SIH-386) |
Biological Description
| Alternative Names | [(E,2S,3R)-2-Amino-3-hydroxyoctadec-4-enyl] dihydrogen phosphate |
| Research Areas | Cell Signaling |
| PubChem ID | 5283560 |
| Scientific Background | D-erythro-Sphingosine-1-phosphate (S1P) is a polar sphingolipid metabolite which regulates diverse cellular responses including cell growth, survival and migration. S1P was reported to stimulate DNA synthesis and cell division in quiescent cultures of Swiss 3T3 fibroblasts and to trigger the dual signal transduction pathways of calcium mobilization and PC-PLD (phospholipase D) activation. S1P serves as a second messenger for intracellular calcium mobilization in U-937 cells (sc-2239) and decreases cellular cAMP. Recent studies show that S1P is a G-protein-coupled receptor (GPCR) ligand for the EDG-1 family, including EDG-1, -3, -5, -6 and -8. This bioactive lipid mediator has been shown to stimulate the ERK pathway and to also counteract the ceramide-induced activation of stress-activated protein kinase (SAPK/JNK). Researchers have also found that S1P is a strong inhibitor of cell motility and phagokinesis in B16 melanoma cells. Additionally, it induces rapid and transient tyrosine phosphorylation of epidermal growth factor receptor (EGFR) and c-Met in gastric cancer cells. S1P has also been known as a tumor-promoting lipid. Suggested to be an activator of GPR3, GPR6, and GPR12. D-erythro-Sphingosine-1-phosphate is an activator of EDG-1, EDG-3, EDG-2, EDG-4 and EDG-5.¬ |
| References |
1. Van Veldhoven P.P., et al. (1989). J. Lipid Res. 30(4): 611-6. 2. Desai N.N., et al. (1992). J. Biol. Chem. 267(32): 23122-8. 3. Sadahira Y., et al. (1992). Proc. Natl. Acad. Sci. U.S.A. 89(20): 9686-90. 4. Olivera A. and Spiegel, S. (1993). Nature. 365(6446): 557-60. 5. Mattie M., et al. (1994). J. Biol. Chem. 269(5): 3181-8. 6. Wu J., et al. (1995). J. Biol. Chem. 270(19): 11484-8. 7. Choi O.H., et al. (1996). Nature. 380(6575): 634-6. 8. Cuvillier O., et al. (1996). Nature. 381(6585): 800-3. 9. Spiegel S., et al. (2000). Biochim. Biophys. Acta. 1484(2-3): 107-16. 10. Spiegel S. and Milstien, S. (2000). FEBS Lett. 476(1-2): 55-57. 11. Shida, D., et al. (2004). FEBS Lett. 577(3): 333-8. 12. Watterson, K.R., et al. (2005). Cell. Signal. 17(3): 289-98. |
Product Images
Chemical structure of Sphingosine-1-phosphate, D-erythro (SIH-386), a Endogenous signaling molecule. CAS #: 26993-30-6. Molecular Formula: C18H38NO5P. Molecular Weight: 379.5 g/mol.
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