D-erythro-Sphingosine-1-phosphate

CAS: 26993-30-6

Ref. TR-S681500

Product Information

• Name: D-erythro-Sphingosine-1-phosphate
• Synonyms: [(E,2S,3R)-2-amino-3-hydroxyoctadec-4-enyl] dihydrogen phosphate, (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
• CAS: 26993-30-6

Description

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),

• Brand: TRC

Chemical properties

• Molecular weight: 379.47
• Formula: C₁₈H₃₈NO₅P
• Color/Form: Neat
• 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-NVGHFZOBSA-N
• SMILES: CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](N)COP(=O)(O)O