857228P

C18 LPA

1-O-octadecyl-2-hydroxy-sn-glycero-3-phosphate (ammonium salt), powder

• Synonym(s): 1-octadecyl-sn-glycero-3-phosphate (ammonium salt); PA(18:0e/0:0)
• Empirical Formula (Hill Notation): C₂₁H₄₈NO₆P
• CAS Number: 799279-67-7
• Molecular Weight: 441.58
• UNSPSC Code: 51191904
• NACRES: NA.25

Properties

• Assay: >99% (LPA; may contain up to 10% of the 2-LPA isomer)
• form: powder
• packaging: pkg of 1 × 1 mg (857228P-1mg)
• manufacturer/tradename: Avanti Research^™ - A Croda Brand 857228P
• lipid type: phospholipids; cardiolipins
• shipped in: dry ice
• storage temp.: −20°C
• SMILES string: O[C@](COP([O-])(O)=O)([H])COCCCCCCCCCCCCCCCCCC.[NH4+]
• InChI: 1S/C21H45O6P.H3N/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-26-19-21(22)20-27-28(23,24)25;/h21-22H,2-20H2,1H3,(H2,23,24,25);1H3/t21-;/m1./s1
• InChI key: FFEGYFZPOUEMED-ZMBIFBSDSA-N

Description

General description

Lysophosphatidic acid (LPA) is a class of phospholipids, which is water-soluble. It has a glycerol backbone attached via a phosphate group, an aliphatic chain and a hydroxyl group. The aliphatic chain is linked to either sn-1 or sn-2 position and the phosphate group is connected to the sn-3 position. The hydroxyl group is linked to the remaining sn-1 or sn-2 position.

Application

C18 LPA or 1-O-octadecyl-2-hydroxy-sn-glycero-3-phosphate may be used:

• to study its effects on Yes-associated protein (YAP) phosphorylation
• as a standard for the quantification of lysophosphatidic acid (LPA) compounds in proton samples using reversed-phase ultra-performance liquid chromatography-tandem mass spectrometer (UPLC-MS/MS)
• as a substrate to investigate the phosphatase activity of soluble epoxide hydrolase (sEH) towards LPA compounds

Biochem/physiol Actions

Lysophosphatidic acid (LPA) is a signaling molecule and alters various cellular responses through G protein-coupled receptors (GPCRs). It stimulates smooth muscle contraction, cytoskeleton rearrangement and chemotaxis. LPA is also involved in inducing neurotransmitter release, cell proliferation, platelet aggregation and Ca²⁺ mobilization. Increased levels of LPA in human plasma leads to ovarian cancer and atherosclerosis. LPA acts as a potential biomarker for ovarian cancer.

Packaging

5 mL Amber Glass Screw Cap Vial (857228P-1mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3