857130C

18:1 Lyso PA

1-oleoyl-2-hydroxy-sn-glycero-3-phosphate (sodium salt), chloroform

• 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

• Assay: >99% (LPA; may contain up to 10% of the 2-LPA isomer, TLC)
• form: liquid
• packaging: pkg of 1 × 2.5 mL (857130C-25mg); pkg of 2 × 4 mL (857130C-200mg)
• manufacturer/tradename: Avanti Polar Lipids 857130C
• concentration: 10 mg/mL (857130C-25mg); 25 mg/mL (857130C-200mg)
• lipid type: cardiolipins; phospholipids
• shipped in: dry ice
• storage temp.: −20°C
• 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

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.

Lysophosphatidic acid (1- or 2-acyl-lysophosphatidic acid/LPA), a bioactive phospholipid is seen at a low level in plasma (~100 nM). 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.

Application

18:1 Lyso PA is suitable:

• for liposome preparations
• to study its apoptotic effect in HeLa cells
• to determine the extraction recovery of LPA at neutral pH and acidic pH by chromatography
• to use as a LPA agonist supplement in oocytes maturation medium to study its effects during in vitro maturation of bovine cumulus–oocyte complexes

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). 1-oleoyl-lysophosphatidic acid (LPA) has the ability to stimulate tyrosine phosphorylation of numerous substrates in Swiss 3T3 cells. It also helps to release calcium from the platelet subcellular fraction.

Packaging

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

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

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Safety Information

• Pictograms: GHS06,GHS08
• Signal Word: Danger
• Hazard Statements: H302 - H315 - H319 - H331 - H336 - H351 - H361d - H372 - H412
• Precautionary Statements: P201 - P273 - P301 + P312 + P330 - P302 + P352 - P304 + P340 + P311 - P308 + P313
• Hazard Classifications: Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 3 - Carc. 2 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 1 - STOT SE 3
• Target Organs: Central nervous system
• Storage Class Code: 6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects
• WGK: WGK 3
• Flash Point(F): does not flash
• Flash Point(C): does not flash