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Merck
CN

S9666

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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About This Item

Empirical Formula (Hill Notation):
C18H38NO5P
CAS Number:
26993-30-6
Molecular Weight:
379.47
UNSPSC Code:
12352211
PubChem Substance ID:
24899853
NACRES:
NA.77
MDL number:
MFCD00270077

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Product Name

Sphingosine 1-phosphate, ≥95%, powder

Quality Level

300

SMILES string

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

InChI key

DUYSYHSSBDVJSM-KRWOKUGFSA-N

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

assay

≥95%

form

powder

storage temp.

−20°C

Gene Information

human ... S1PR1(1901), S1PR2(9294), S1PR3(1903), S1PR4(8698), S1PR5(53637)

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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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000488213
0000488213
0000431191
0000431191
0000415546

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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
William S Szczepaniak et al.
Translational research : the journal of laboratory and clinical medicine, 152(5), 213-224 (2008-11-18)
S1P has been demonstrated to protect against the formation of lipopolysaccharide (LPS)-induced lung edema when administered concomitantly with LPS. In the current study, we sought to determine the effectiveness of S1P to attenuate lung injury in a translationally relevant canine
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
H Okamoto et al.
Molecular and cellular biology, 20(24), 9247-9261 (2000-11-30)
Sphingosine-1-phosphate (S1P) is a bioactive lysophospholipid that induces a variety of biological responses in diverse cell types. Many, if not all, of these responses are mediated by members of the EDG (endothelial differentiation gene) family G protein-coupled receptors EDG1, EDG3
Emmanuel E Egom et al.
Current opinion in lipidology, 24(4), 351-356 (2013-05-09)
The absolute level of HDL cholesterol (HDL-C) may not be the only criterion contributing to their antiatherothrombotic effects. This review focuses on evidence in support of the concept that HDL-bound sphingosine-1-phosphate (S1P) plays a role in different HDL atheroprotective properties
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Product Information Sheet - S9666

Product Information Sheet

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