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Sphingosine-1-Phosphate (d18:1) | 860492

D-erythro-sphingosine-1-phosphate

860492P

Powder

1 mg
$185.00
5 mg
$520.00
10 mg
$740.00
25 mg
$1340.00
50 mg
$2080.00

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  • Solubility
Sphingosine-1-phosphate (S1P), a zwitterionic sphingolipid, is an important cellular metabolite and signalling lipid in animal cells. It has also been found in insects, yeasts and plants. You can find additional information on S1P at the following link:
 
Molecular Formula
C18H38NO5P
Percent Composition
C 56.97%, H 10.09%, N 3.69%, O 21.08%, P 8.16%
Purity
>99%
Stability
1 Years
Storage
-20°C
CAS Number
26993-30-6
CAS Registry Number is a Registered Trademark of the American Chemical Society
Molecular Weight
379.472
Exact Mass
379.249
Synonyms
sphingosine d18 D erythro 2S,3R,4(E) 1-phosphate
(2S,3R,4E)-2-aminooctadec-4-ene-1,3-diol-1-Phosphate
(2S,3R,4E)-2-amino-1,3-octadec-4-enediol-1-Phosphate
S1P
sphing-4-enine-1-phosphate
Download
Notes
GIF Graphics File. 
GIF Graphics File. 
MDL Molfile. 
CDX File. 
Abuhusain, H.J., A. Matin, Q. Qiao, H. Shen, N. Kain, B.W. Day, B.W. Stringer, B. Daniels, M.A. Laaksonen, C. Teo, K.L. McDonald, and A.S. Don. (2013). A metabolic shift favouring sphingosine 1-phosphate at the expense of ceramide controls glioblastoma angiogenesis. J Biol Chem [PubMed]

Allende, M.L., L.M. Sipe, G. Tuymetova, K.L. Wilson-Henjum, W. Chen, and R.L. Proia. (2013). Sphingosine-1-phosphate Phosphatase 1 Regulates Keratinocyte Differentiation and Epidermal Homeostasis. J Biol Chem 288:18381-18391. [PubMed]

Liang, J., M. Nagahashi, E.Y. Kim, K.B. Harikumar, A. Yamada, W.C. Huang, N.C. Hait, J.C. Allegood, M.M. Price, D. Avni, K. Takabe, T. Kordula, S. Milstien, and S. Spiegel. (2013). Sphingosine-1-Phosphate Links Persistent STAT3 Activation, Chronic Intestinal Inflammation, and Development of Colitis-Associated Cancer. Cancer Cell 23:107-20. [PubMed]

Karuna, R., R. Park, A. Othman, A.G. Holleboom, M.M. Motazacker, I. Sutter, J.A. Kuivenhoven, L. Rohrer, H. Matile, T. Hornemann, M. Stoffel, K.M. Rentsch, and A. von Eckardstein. (2011). Plasma levels of sphingosine-1-phosphate and apolipoprotein M in patients with monogenic disorders of HDL metabolism. Atherosclerosis 219:855-63. [PubMed]

Sphingosine-1-Phosphate Solubility Protocol & Cell Delivery

 

Organic Solutions:
The solubility of stock solutions of sphingoid base 1-phosphates may be increased by the addition of dimethylamine.

Water Solutions:
Solubility of S1P is difficult using organic solvents so typically it is suspended in methanol to aliquot, the methanol dried and the residue dispersed using fatty acid free BSA solution.
A procedure for preparation of a S1P stock solution follows:

Stock Solution:
125µM Sphingosine-1-Phosphate in essentially fatty acid free Bovine Serum Albumin (BSA, 4mg/ml)

Preparation of Stock Solution:
Methanol Solution:

  • Add Sphingosine-1-phosphate to methanol:water 95:5 (0.5mg/ml)
  • Heat mixture (45°C-65°C methanol boiling point) and sonicate until Sphingosine-1-Phosphate is suspended (solutions are not clear - forms a slightly hazy suspention).
  • Transfer desired amounts of methanol:water stock solution to glass vessel.
  • Remove methanol:water solution using a stream of dry nitrogen.
  • Place glass vessel into a warm (approximately 50°C) water bath.
  • Rotate glass vessel during evaporation to make thin film of Sphingosine-1-phosphate on tube wall.
  • Store Sphingosine-1-Phosphate at -20°C in closed container.

    Maximum storage one year.

BSA Solution

  • Add enough BSA (4mg/ml) in water at 37°C to glass vessel containing Sphingosine-1-Phosphate
    to make a 125µM Sphingosine-1-Phosphate solution.
  • Incubate for 30 minutes and vortex occasionally.
  • Maximum storage three months.