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S9666

Sigma-Aldrich

Sphingosine 1-phosphate

≥95% (TLC), powder, lipid second messenger

Synonym(s):

(2S,3R,4E)-2-Amino-4-octadecene-1,3-diol 1-phosphate, D-erythro-Sphingosine 1-phosphate

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1 MG
₪2,198.00

About This Item

Empirical Formula (Hill Notation):
C18H38NO5P
CAS Number:
Molecular Weight:
379.47
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.77

₪2,198.00


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Product Name

Sphingosine 1-phosphate, ≥95%, powder

Quality Level

Assay

≥95%

form

powder

storage temp.

−20°C

SMILES string

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

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

DUYSYHSSBDVJSM-KRWOKUGFSA-N

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Biochem/physiol Actions

A lipid second messenger that binds to S1P1 and S1P3 receptors. Mobilizes intracellular Ca2+ stores and decreases cellular cAMP. Activates phospholipase D. S1P stimulates the migration of endothelial cells but inhibits the migration of other cell types. Induces angiogenesis.

Features and Benefits

This compound is featured on the Lysophospholipid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Kaiqi Sun et al.
Nature communications, 7, 12086-12086 (2016-07-16)
Sphingosine-1-phosphate (S1P) is a bioactive signalling lipid highly enriched in mature erythrocytes, with unknown functions pertaining to erythrocyte physiology. Here by employing nonbiased high-throughput metabolomic profiling, we show that erythrocyte S1P levels rapidly increase in 21 healthy lowland volunteers at
Gregory T Kunkel et al.
Nature reviews. Drug discovery, 12(9), 688-702 (2013-08-21)
The bioactive lipid sphingosine-1-phosphate (S1P) is involved in multiple cellular signalling systems and has a pivotal role in the control of immune cell trafficking. As such, S1P has been implicated in disorders such as cancer and inflammatory diseases. This Review
Alexander Koch et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 31(6), 745-760 (2013-06-06)
Because of its highly bioactive properties sphingosine 1-phosphate (S1P) is an attractive target for the treatment of several diseases. Since the expression of sphingosine kinases as well as S1P receptors was demonstrated in the kidney, questions about the physiological and
Roland Martin et al.
Current topics in microbiology and immunology, 378, 149-170 (2014-04-15)
The development of fingolimod, an unselective functional antagonist of the interactions between sphingosine 1 phosphate (S1P) and sphingosine 1 phosphate receptors (S1PRs), as the first oral therapy for multiple sclerosis (MS) has been a milestone. The parallel intensive research on
Tsuyoshi Nishi et al.
Biochimica et biophysica acta, 1841(5), 759-765 (2013-08-08)
Sphingosine 1-phosphate (S1P) is a lipid mediator that plays important roles in diverse cellular functions such as cell proliferation, differentiation and migration. S1P is synthesized inside the cells and subsequently released to the extracellular space, where it binds to specific

Articles

Discover Bioactive Small Molecules for Lipid Signaling Research

Questions

  1. Will using methanol as a solvent to dissolve the powder affect or disrupt the huvect cell line?

    1 answer
    1. Another supplier (APExBIO) suggests using a solvent of 0.3M NaOH for in vitro work, as the substance is soluble in it at less than 4 mg/mL. They also recommend warming the tube at 37°C and shaking it in an ultrasonic bath for a while to achieve higher solubility. The stock solution can be stored below -20°C for several months.

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