Skip to Content
Merck
CN

Key Documents

View All Documentation

857130C

Avanti

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

Sign In to View Organizational & Contract Pricing.

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):
C21H40O7PNa
CAS Number:
325465-93-8
Molecular Weight:
458.50
MDL number:
MFCD00133427
UNSPSC Code:
51191904
NACRES:
NA.25
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Product Name

18:1 Lyso PA, 1-oleoyl-2-hydroxy-sn-glycero-3-phosphate (sodium salt), chloroform

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 Research™ - A Croda Brand 857130C

concentration

10 mg/mL (857130C-25mg), 25 mg/mL (857130C-200mg)

lipid type

cardiolipins
phospholipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

[Na+].[P](=O)([O-])(OC[C@H](O)COC(=O)CCCCCCC\C=C/CCCCCCCC)O

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

General description

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.
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.

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

Still not finding the right product?

Explore all of our products under 18:1 Lyso PA

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

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, Liver,Kidney

Storage Class

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

Regulatory Information

危险化学品
易制毒化学品（2类）

This item has

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

It looks like we've run into a problem, but you can still download Certificates of Analysis from our Documents section.

If you need assistance, please contact Customer Support

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Lysophosphatidic acids. Influence on platelet aggregation and intracellular calcium flux.
Gerrard JM, et al.
The American Journal of Pathology, 96(2), 423-423 (1979)
The effect of lysophosphatidic acid during in vitro maturation of bovine cumulus- oocyte complexes: cumulus expansion, glucose metabolism and expression of genes involved in the ovulatory cascade, oocyte and blastocyst competence
Boruszewska D, et al.
Reproductive Biology and Endocrinology, 13(1), 44-44 (2015)
Ethan Sagher et al.
Cancer cell international, 14, 75-75 (2014-10-18)
The small molecule NSC676914A was previously identified as an NF-κB inhibitor in TPA-stimulated HEK293 cells (Mol Can Ther 8:571-581, 2009). We hypothesized that this effect would also be seen in ovarian cancer cells, and serve as its mechanism of cytotoxicity.
View All Related Papers

Global Trade Item Number

SKUGTIN
857130C-200MG04061837793172
857130C-25MG04061837793189