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860662P

Avanti

Sphingosine-1-Phosphate (d20:1)

Avanti Research™ - A Croda Brand 860662P, powder

Synonym(s):

D-erythro-sphingosine-1-phosphate (C20 base)

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About This Item

Empirical Formula (Hill Notation):
C20H42NO5P
CAS Number:
799812-75-2
Molecular Weight:
407.52
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 1 mg (860662P-1mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 860662P

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

[H][C@](/C=C/CCCCCCCCCCCCCCC)(O)[C@]([NH3+])([H])COP([O-])(O)=O

InChI

1S/C20H42NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(22)19(21)18-26-27(23,24)25/h16-17,19-20,22H,2-15,18,21H2,1H3,(H2,23,24,25)/b17-16+/t19-,20+/m0/s1

InChI key

YUUWWSOTAGQJFW-YIVRLKKSSA-N

General description

Sphingosine-1-phosphate (S1P) is a zwitterionic sphingolipid. It is found in insects, yeasts and plants. Sphingosine-1-Phosphate (d20:1) is a phosphorylated derivative of long chain base C20 sphingosine.

Application

Sphingosine-1-phosphate (S1P)-d7 has been used as a reference standard in liquid chromatography/tandem mass spectrometry analysis for quantitative analyses of S1P d20:1 in central nervous system of healthy mice and in human glioblastoma tissue.

Biochem/physiol Actions

Sphingosine-1-phosphate (S1P) is an important cellular metabolite and signaling lipid in animal cells. It aids in various physiological and cellular processes such as atherosclerosis, inflammation, immunity, tumorigenesis, and cell proliferation. S1P plays a vital role in mammalian brain and cardiac development. S1P d20:1 serves as a partial agonist at the S1P receptor 2 (S1P2). It has an ability to inhibit S1P d18:1‐mediated cyclooxygenase 2(COX2) induction.

Packaging

5 mL Amber Glass Screw Cap Vial (860662P-1mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Henrik Fyrst et al.
Nature chemical biology, 6(7), 489-497 (2010-06-19)
Sphingolipids comprise a complex family of naturally occurring molecules that are enriched in lipid rafts and contribute to their unique biochemical properties. Membrane sphingolipids also serve as a reservoir for bioactive metabolites including sphingosine, ceramide, sphingosine-1-phosphate and ceramide-1-phosphate. Among these
Michael Maceyka et al.
Trends in cell biology, 22(1), 50-60 (2011-10-18)
The bioactive sphingolipid metabolite sphingosine-1-phosphate (S1P) is now recognized as a critical regulator of many physiological and pathophysiological processes, including cancer, atherosclerosis, diabetes and osteoporosis. S1P is produced in cells by two sphingosine kinase isoenzymes, SphK1 and SphK2. Many cells
Rajkumar Vutukuri et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 34(3), 3932-3942 (2020-01-17)
Sphingosine 1-phosphate (S1P) signaling influences numerous cell biological mechanisms such as differentiation, proliferation, survival, migration, and angiogenesis. Intriguingly, our current knowledge is based solely on the role of S1P with an 18-carbon long-chain base length, S1P d18:1. Depending on the

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