857130P

18:1 Lyso PA

Avanti Research^™ - A Croda Brand

• Synonym(s): oleoyl lysophosphatidic acid; 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate (sodium salt); PA(18:1(9Z)/0:0); 18:1 LPA; o-LPA; 110681
• Empirical Formula (Hill Notation): C₂₁H₄₀O₇PNa
• CAS Number: 325465-93-8
• Molecular Weight: 458.50
• UNSPSC Code: 51191904
• NACRES: NA.25

Properties

• description: 1-oleoyl-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 × 1 g (857130P-1g); pkg of 2 × 100 mg (857130P-200mg); pkg of 1 × 25 mg (857130P-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(CCCCCCC/C=C\CCCCCCCC)=O.[Na+]
• InChI: 1S/C21H41O7P.Na/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26;/h9-10,20,22H,2-8,11-19H2,1H3,(H2,24,25,26);/q;+1/p-1/b10-9-;/t20-;/m1./s1
• InChI key: XGRLSUFHELJJAB-JGSYTFBMSA-M

Description

General description

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

Application

18:1 Lyso PA or 1-oleoyl-2-hydroxy-sn-glycero-3-phosphate has been used: to study its effects on intracellular calcium concentration [Ca²⁺]i transient in pheochromocytoma cell 12 (PC12) cells and primary astrocytes. It has also been used to study its effects on blood glucose level and physical endurance in fasted mice.

Biochem/physiol Actions

Biological responses to LPA: Cell Proliferation, Inhibition of differentiation (neuroblastoma cells, myoblasts), Platelet aggregation, Smooth muscle contraction, Neurotransmitter release, Stress fibre formation/cell rounding/neurite retraction, Cell-surface-fibronectin binding, Tumor cell invasion, Chemotaxis (dictyostelium amoebae), Cl--mediated membrane depolarization (fibroblasts), Inhibition of connexin 43 based cell-cell communication, Increased tight junction permeability (brain endothelial cells). Note: The bioactivity of LPA appears to require long (i.e., C16 to C18) acyl carbon chains of the type usually found associated with membrane lipids although optimum requirements for a single type of acyl carbon chain are not universal. The bioactivity decreases with shorter chain length. In serum, oleoyl and palmitoyl fatty acid containing LPA are the predominant species.

Packaging

5 mL Clear Glass Sealed Ampule (857130P-200mg)

5 mL Clear Glass Sealed Ampule (857130P-25mg)

60 mL Amber Wide Mouth Screw Cap Glass Bottle (857130P-1g)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Safety Information

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