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850104P

Avanti

18:0 Lyso PI

1-stearoyl-2-hydroxy-sn-glycero-3-phosphoinositol (ammonium salt), powder

Sinónimos:

1-octadecanoyl-2-hydroxy-sn-glycero-3-phospho-(1′-myo-inositol) (ammonium salt); PI(18:0/0:0); 110719

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About This Item

Fórmula empírica (notación de Hill):
C27H56NO12P
Número de CAS:
849412-49-3
Peso molecular:
617.71
UNSPSC Code:
51191904
NACRES:
NA.25

assay

>99% (LPI; may contain up to 10% of the 2-LPI isomer, TLC)

form

powder

packaging

pkg of 1 × 100 μg (with stopper and crimp cap (850104P-100ug))
pkg of 1 × 500 μg (with stopper and crimp cap (850104P-500ug))

manufacturer/tradename

Avanti Research™ - A Croda Brand 850104P

lipid type

phosphoglycerides

shipped in

dry ice

storage temp.

−20°C

SMILES string

[H][C@@](COP([O-])(O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O)=O)(O)COC(CCCCCCCCCCCCCCCCC)=O.[NH4+]

InChI

1S/C27H53O12P.H3N/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(29)37-18-20(28)19-38-40(35,36)39-27-25(33)23(31)22(30)24(32)26(27)34;/h20,22-28,30-34H,2-19H2,1H3,(H,35,36);1H3/t20-,22-,23-,24+,25-,26-,27-;/m1./s1

InChI key

QVEDYTZLCBLSCH-FJYNCLFYSA-N

General description

Lysophosphatidylinositol (LPI), an acidic lysophosholipid, carries inositol in its head group.

Application

18:0 Lyso PI (1-stearoyl-2-hydroxy-sn-glycero-3-phosphoinositol) has been used as lysophosphatidylinositol (LPI) substrate in lysophosphatidylinositol acyltransferase biochemical assay to determine lyso-phosphatidylinositol acyltransferase (LPIAT) activity of liver microsomes. It may be used as a synthetic LPI to compare its effects with liver LPI in transferrin (Tf) endocytosis. It may also be used as LPI standard to quantify serum LPI levels in gonadectomized rats.

Biochem/physiol Actions

Increased circulating levels of L-alpha-lysophosphatidylinositol (LPI) are associated with cancer and LPI is a potent ligand for the G-protein-coupled receptor GPR55.
Lysophosphatidylinositol (LPI) displays mitogenic activity and can serve as a bioactive lysophospholipid mediator. It may be considered as a lipid mediator.

Packaging

2 mL Amber Serum Vial with Stopper and Crimp Cap (850104P-100ug)
2 mL Amber Serum Vial with Stopper and Crimp Cap (850104P-500ug)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

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Referencia del producto
Descripción
Precios

Storage Class

11 - Combustible Solids

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Monica Imbernon et al.
Molecular and cellular endocrinology, 383(1-2), 159-169 (2014-01-01)
The G protein-coupled receptor GPR55 has been proposed as a new cannabinoid receptor associated with obesity in humans. We have investigated the regulation of GPR55 in rat white adipose tissue (WAT) in different physiological and pathophysiological settings involved in energy
Robert N Helsley et al.
eLife, 8 (2019-10-18)
Recent studies have identified a genetic variant rs641738 near two genes encoding membrane bound O-acyltransferase domain-containing 7 (MBOAT7) and transmembrane channel-like 4 (TMC4) that associate with increased risk of non-alcoholic fatty liver disease (NAFLD), non-alcoholic steatohepatitis (NASH), alcohol-related cirrhosis, and
Mariachiara Bianco et al.
Food chemistry, 324, 126878-126878 (2020-04-29)
Ceramides (Cer) and cerebrosides are important sphingolipids (SL) involved in many biological processes. Herein, the SL content of yellow lupin seeds (Lupinus luteus) was determined by liquid-liquid extraction, mild alkaline hydrolysis (1 h at 37 °C) and reversed-phase liquid chromatography with negative
Saori Oka et al.
Biochemical and biophysical research communications, 362(4), 928-934 (2007-09-04)
GPR55 is an orphan G protein-coupled receptor. In this study, we explored a possible endogenous ligand for GPR55 using HEK293 cells which expressed GPR55. We found that lysophosphatidylinositol induced rapid phosphorylation of the extracellular signal-regulated kinase in transiently or stably
Ieva Ailte et al.
Scientific reports, 6, 30336-30336 (2016-07-28)
Shiga toxin (Stx), an AB5 toxin, binds specifically to the neutral glycosphingolipid Gb3 at the cell surface before being transported into cells. We here demonstrate that addition of conical lysophospholipids (LPLs) with large head groups inhibit Stx binding to cells

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