CAS 26993-30-6

Sphingosine-1-phosphate

Description:

Sphingosine-1-phosphate (S1P) is a bioactive lipid molecule that plays a crucial role in various physiological processes, including cell proliferation, survival, migration, and immune responses. It is a sphingolipid metabolite derived from sphingosine, which is phosphorylated by sphingosine kinases. S1P is characterized by its ability to act as a signaling molecule, binding to specific G protein-coupled receptors (S1P receptors) that mediate diverse cellular responses. The substance is soluble in organic solvents and exhibits amphipathic properties, allowing it to interact with both hydrophilic and hydrophobic environments. S1P is involved in the regulation of vascular integrity, lymphocyte trafficking, and neuroprotection, making it significant in both health and disease contexts, including cancer and autoimmune disorders. Its concentration is tightly regulated within cells and extracellular spaces, as it can have different effects depending on its localization and the receptors it activates. Overall, Sphingosine-1-phosphate is a vital component of cellular signaling pathways with implications in various biological functions and therapeutic targets.

Formula: C₁₈H₃₈NO₅P

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

InChI key: InChIKey=DUYSYHSSBDVJSM-KRWOKUGFSA-N

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

Synonyms:

• (4E)-2-Amino-3-hydroxy-4-octadecen-1-yl dihydrogen phosphate
• (4E)-2-Amino-3-hydroxy-4-octadecen-1-yldihydrogen-phosphat
• (4E)-2-amino-3-hydroxyoctadec-4-en-1-yl dihydrogen phosphate
• 4-Octadecene-1,3-diol, 2-amino-, 1-(dihydrogen phosphate), (2S,3R,4E)-
• 4-Octadecene-1,3-diol, 2-amino-, 1-(dihydrogen phosphate), (E)-<span class="text-smallcaps">D</span>-erythro-
• 4-Octadecene-1,3-diol, 2-amino-, 1-(dihydrogen phosphate), [R-[R*,S*-(E)]]-
• <span class="text-smallcaps">D</span>-erythro-Sphingosine-1-phosphate
• C₁₈-Sphingosine 1-phosphate
• Dihydrogène phosphate de (4E)-2-amino-3-hydroxy-4-octadécèn-1-yle
• Proteins, S1P
• S1P protein
• Sphingosine 1-phosphate
• Sphingosine 1-phosphic acid
• D-erythro-Sphingosine-1-phosphate
• D-erythro-Sphingosine 1-phosphate

Sphingosine-1-phosphate

CAS: 26993-30-6

S1P: agonist for S1P1-5, ligand for GPR3/6/12, intracellular messenger, mobilizes Ca2+, made from sphingosine.

Formula: C₁₈H₃₈NO₅P

Purity: 98.00% - >99.99%

Color and Shape: Solid

Molecular weight: 379.47

Ref: TM-T21500

Sphingosine-1-phosphate

CAS: 26993-30-6

Sphingosine-1-phosphate

Purity: ≥98%

Molecular weight: 379.47g/mol

Ref: 54-BUP20986

Sphingosine 1-phosphate

CAS: 26993-30-6

Formula: C₁₈H₃₈NO₅P

Purity: ≥ 98.0%

Color and Shape: White to pale yellow powder

Molecular weight: 379.47

Ref: 7W-GL7075

D-erythro-Sphingosine-1-Phosphate

CAS: 26993-30-6

Formula: C18H38NO5P

Purity: >98%

Color and Shape: Solid

Molecular weight: 379.47

Ref: 48-56-1311

D-erythro-Sphingosine-1-phosphate-13C2,D2

Controlled Product

CAS: 26993-30-6

Stability Moisture, Temperature Sensitive; Hygroscopic
Applications A labelled putative lipid second messenger; found to inhibit cellular mobility of melanoma cells at very low concentrations with no toxic effects thereby making it a possible agent for prevention of tumor cell metastasis and inflammatory processes; mobilizes intracellular calcium stores; decreases cellular cAMP; activates phospholipase D; does not inhibitprotein kinase C.
References Zhang, H., et al.: J. Cell Biol., 114, 155 (1991) Sadahira, Y., et al.: Proc. Natl. Acad. Sci. USA (1992), Cuvillier, O., et al.: Nature, 381, 800 (1996)

Formula: C₁₆₁₃C₂H₃₆D₂NO₅P

Color and Shape: Neat

Molecular weight: 383.47

Ref: TR-S681502

D-erythro-Sphingosine-1-Phosphate

CAS: 26993-30-6

Stability Moisture, Temperature Sensitive; Hygroscopic
Applications A putative lipid second messenger; found to inhibit cellular mobility of melanoma cells at very low concentrations with no toxic effects thereby making it a possible agent for prevention of tumor cell metastasis and inflammatory processes. It mobilizes intracellular calcium stores, decreases cellular cAMP, activates phospholipase D and does not inhibitprotein kinase C.
References Yeh, C., et al.: Am. J. Physiol., 296, H1193 (2009), Hagen, N., et al.: J. Biol. Chem., 284, 11346 (2009), Kuehnel, M., et al.: J. Cell Sci., 122, 499 (2009),

Formula: C₁₈H₃₈NO₅P

Color and Shape: Neat

Molecular weight: 379.47

Ref: TR-S681500

D-erythro-Sphingosine 1-phosphate

CAS: 26993-30-6

D-Erythro-sphingosine 1-phosphate (D-ESP) is a phospholipid that belongs to the sphingosine family. It binds to cell surface receptors and has a variety of physiological effects such as increasing intracellular levels of Ca2+ and inhibiting platelet aggregation. D-ESP has been shown to inhibit the enzyme adenylyl cyclase, which converts ATP into cAMP, in the presence of chemical inhibitors. This inhibition can be reversed by the addition of cAMP or by adding adenylyl cyclase activators such as forskolin. D-ESP also inhibits phosphorylation of c-Jun and affects gene transcription, protein synthesis and cellular physiology.

Formula: C₁₈H₃₈NO₅P

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 379.47 g/mol

Ref: 3D-FD57792