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About This Item
Empirical Formula (Hill Notation):
C18H38NO5P
CAS Number:
Molecular Weight:
379.47
MDL number:
UNSPSC Code:
12352211
NACRES:
NA.25
Product Name
Sphingosine-1-Phosphate (d18:1), Avanti Research™ - A Croda Brand
SMILES string
[H][C@](/C=C/CCCCCCCCCCCCC)(O)[C@]([NH3+])([H])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
assay
>99% (TLC)
form
powder
packaging
pkg of 1 × 1 mg (860492P-1mg)
pkg of 1 × 25 mg (860492P-25mg)
pkg of 1 × 5 mg (860492P-5mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand
lipid type
sphingolipids
shipped in
dry ice
storage temp.
−20°C
Packaging
5 mL Amber Glass Screw Cap Vial (860492P-25mg)
5 mL Amber Glass Screw Cap Vial (860492P-5mg)
5 mL Amber Glass Screw Cap Vial (860492P-1mg)
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
Application
Sphingosine-1-Phosphate (d18:1) has been used:
- as an internal standard in high performance liquid chromatography (HPLC) for the quantification of plasma lipid sphingosine-1-phosphate(S1P)
- to evaluate its chemotactic response of auto reactive immature B cells
- to test its effect on autophagy and preconditioning in oxygen and glucose deprived neurons
Biochem/physiol Actions
Sphingosine 1-phosphate (S1P) is a signaling molecule and an intracellular messenger, crucial for the physiological processes. It is implicated in the pathogenesis of osteoporosis, cancer, atherosclerosis and diabetes. S1P regulates skin dendritic cells and keratinocytes, and its anti-inflammatory functionality is useful in treating atopic dermatitis. S1P coordinates T lymphocytes circulation in lymph, plasma and tissue by interacting with G-protein coupled receptors (GPCRS). S1P is a high affinity ligand for sphingosine-1-phosphate receptor (S1P1−5).
General description
Sphingosine-1-phosphate (S1P), a sphingolipid, is an important cellular metabolite and signaling lipid in animal cells. It has also been found in yeasts and plants. Sphingosine kinases (SPKs) catalyzes the synthesis of S1P from spingosine and regulates S1P levels. It is the end product of ceramide catabolism and is metabolized to phosphoethanolamine and hexadecenal by S1P lyase. S1P is produced in endothelial cells.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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S1P3 confers differential S1P-induced migration by autoreactive and non-autoreactive immature B cells and is required for normal B-cell development
Donovan EE, et al.
European Journal of Immunology, 40(3), 688-698 (2010)
High-Throughput Assays to Measure Intracellular Ca 2+ Mobilization in Cells that Express Recombinant S1P Receptor Subtypes
Valentine WJ and Tigyi G
Methods in Molecular Biology, 77-87 (2012)
Liheng Shi et al.
Journal of the American Heart Association, 8(22), e013673-e013673 (2019-11-09)
Background We recently discovered a small endogenous peptide, peptide Lv, with the ability to activate vascular endothelial growth factor receptor 2 and its downstream signaling. As vascular endothelial growth factor through vascular endothelial growth factor receptor 2 contributes to normal
Collin Tran et al.
Journal of neurochemistry, e14917-e14917 (2019-11-20)
Sphingosine 1-phosphate (S1P) is an essential lipid metabolite that signals through a family of five G protein-coupled receptors, S1PR1-S1PR5, to regulate cell physiology. The multiple sclerosis drug Fingolimod (FTY720) is a potent S1P receptor agonist that causes peripheral lymphopenia. Recent
Liao-Liao Hu et al.
Cells, 8(11) (2019-11-17)
CCN1 and CCN2 are members of the CCN family and play essential roles in the regulation of multiple female reproductive functions, including ovulation. Cyclooxygenase-2 (COX2) is a critical mediator of ovulation and can be induced by sphingosine-1-phosphate (S1P) through the
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