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Merck
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857128P

Avanti

18:0 Lyso PA

Avanti Research™ - A Croda Brand

Synonym(s):

1-octadecanoyl-sn-glycero-3-phosphate (sodium salt); stearoyl lysophosphatidic acid; PA(18:0/0:0); 18:0 LPA; s-LPA; 110680

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About This Item

Empirical Formula (Hill Notation):
C21H42O7PNa
CAS Number:
325465-92-7
Molecular Weight:
460.52
UNSPSC Code:
51191904
NACRES:
NA.25

Key Documents

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description

1-stearoyl-2-hydroxy-sn-glycero-3-phosphate (sodium salt)

Assay

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

form

powder

packaging

pkg of 1 × 25 mg (857128P-25mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand

lipid type

cardiolipins
phospholipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

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

InChI key

YJQFVAZHPIBPHN-VEIFNGETSA-M

General description

Lysophosphatidic acid (1- or 2-acyl-lysophosphatidic acid/LPA), a bioactive phospholipid is seen at a low level in plasma (~100nM). It is usually formed during the synthesis of phospholipid of cell membranes. It is produced by various cells like, activated platelets, epithelial cells, leukocytes, neuronal cells and tumor cells. 18:0 Lyso PA has stearic acid at sn-1 and a hydroxyl group at sn-2 position.

Application

18:0 Lyso PA is suitable for use:
  • to determine the extraction recovery of LPA at neutral pH and acidic pH by chromatographic method
  • to use as internal standard to study the role of intestinally derived lysophosphatidic acid in dyslipidemia and atherosclerosis
  • to investigate its effects on clathrin?dependent endocytosis

Biochem/physiol Actions

Lysophosphatidic acid (1- or 2-acyl-lysophosphatidic acid/LPA) modulates cell motility, proliferation, invasion, survival and production of growth factors via G protein-coupled receptor (GPCR).

Packaging

5 mL Amber Glass Screw Cap Vial (857128P-25mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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Lysophosphatidic acid triggers apoptosis in HeLa cells through the upregulation of tumor necrosis factor receptor superfamily member 21
Dong Y, et al.
Mediators of Inflammation, 2017 (2017)
Exogenous lysophospholipids with large head groups perturb clathrin-mediated endocytosis
Ailte I, et al.
Traffic, 18(3), 176-191 (2017)
Quantitative determination of lysophosphatidic acid by LC/ESI/MS/MS employing a reversed phase HPLC column
Shan L, et al.
Journal of Chromatography. B, Biomedical Sciences and Applications, 864(1-2), 22-28 (2008)
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
Jesica R Williams et al.
The Journal of biological chemistry, 284(25), 17304-17319 (2009-04-16)
Lysophosphatidic acid (LPA) is a ligand for LPA(1-3) of the endothelial differentiation gene family G-protein-coupled receptors, and LPA(4-8) is related to the purinergic family G-protein-coupled receptor. Because the structure-activity relationship (SAR) of GPR92/LPA(5) is limited and whether LPA is its
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