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860492P

Avanti

Sphingosine-1-Phosphate (d18:1)

Avanti Polar Lipids

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Synonym(s):
D-erythro-sphingosine-1-phosphate
Empirical Formula (Hill Notation):
C18H38NO5P
CAS Number:
26993-30-6
Molecular Weight:
379.47
NACRES:
NA.25

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 Polar Lipids

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

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

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.

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).

Packaging

5 mL Amber Glass Screw Cap Vial (860492P-1mg)
5 mL Amber Glass Screw Cap Vial (860492P-25mg)
5 mL Amber Glass Screw Cap Vial (860492P-5mg)

also commonly purchased with this product

Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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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
Suwon Jeon et al.
Journal of lipid research, 61(1), 20-32 (2019-11-07)
Sphingosine 1-phosphate (S1P) lyase is an intracellular enzyme that catalyzes the irreversible degradation of S1P and has been suggested as a therapeutic target for the treatment of psoriasis vulgaris. Because S1P induces differentiation of keratinocytes, we examined whether modulation of
Preconditioning stimuli induce autophagy via sphingosine kinase 2 in mouse cortical neurons
Sheng R, et al.
The Journal of Biological Chemistry, 289(30), 20845-20857 (2014)
Effects of apolipoprotein M in uremic atherosclerosis
Bosteen MH, et al.
Atherosclerosis, 265(3), 93-101 (2017)
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