857119P

06:0 Lyso PA

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

• Synonym(s): 1-hexanoyl-sn-glycero-3-phosphate (ammonium salt); PA(6:0/0:0)
• Empirical Formula (Hill Notation): C₉H₂₂NO₇P
• CAS Number: 384835-45-4
• Molecular Weight: 287.25
• NACRES: NA.25

Properties

• assay: >99% (LPA; may contain up to 10% of the 2-LPA isomer, TLC)
• form: powder
• packaging: pkg of 1 × 25 mg (857119P-25mg)
• manufacturer/tradename: Avanti Polar Lipids 857119P
• shipped in: dry ice
• storage temp.: −20°C
• SMILES string: O[C@](COP([O-])(O)=O)([H])COC(CCCCC)=O.[NH4+]

Description

General description

Lysophosphatidic acid (LPA) belongs to a class of phospholipids, that has a glycerol backbone attached by a phosphate group, an aliphatic chain and a hydroxyl group. It has a phosphate group attached to sn-3 position, an aliphatic chain attached to sn-1 or sn-2 position and the hydroxyl group attached to the remaining sn-1 or sn-2 position. 06:0 Lyso PA/HHGP, belongs to the LPA (lysophosphatidic acid) family. It is a negatively charged single chain lipid.

Lysophosphatidic acid (LPA) has a free hydroxyl and phosphate moiety. It is hydrophilic and is not associated with the membrane. It is the major constituent of serum.

Application

06:0 Lyso PA (LPA) has been used in the structure-activity relationship (SAR) analysis with G-protein receptor GPR92. It has also been used in lipid assay in the treatment of serum-starved primary mouse embryonic fibroblast cells.

06:0 Lyso PA has been used to study the role of lipid binding to MxiM protein in co‐crystallization experiments.

Biochem/physiol Actions

Lysophosphatidic acid (LPA) participates in several biological functions. LPA stimulates platelet aggregation, chemotaxis, cytoskeleton rearrangement, Ca²⁺ mobilization and cell proliferation. 06:0 Lyso PA/HHGP possesses a micromolar binding affinity for global regulator of LEE (locus of enterocyte effacement) repressor (GrlR) and for β-lactoglobulin.

Lysophosphatidic acid (LPA) is the precursor for the synthesis of phospholipids in eukaryotes and prokaryotes. It acts as an intercellular signaling molecule. Activated platelets produce LPA. It plays a major role in tissue healing and wound regeneration. LPA binds to G-protein coupled receptors. It possesses mitogenic properties. LPA inhibits differentiation of neuroblastoma and myoblast, aids in neurotransmitter release and smooth muscle contraction. It is a potential biomarker for ovarian and gynecological cancers. It is implicated in the initiation of neuropathic pain.

Packaging

5 mL Amber Glass Screw Cap Vial (857119P-25mg)

Safety Information

• Storage Class Code: 13 - Non Combustible Solids