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857130P

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

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About This Item

Empirical Formula (Hill Notation):
C21H40O7PNa
CAS Number:
325465-93-8
Molecular Weight:
458.50
UNSPSC Code:
51191904
NACRES:
NA.25

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

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

also commonly purchased with this product

Product No.
Description
Pricing

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Yunzhou Dong et al.
Mediators of inflammation, 2017, 2754756-2754756 (2017-03-30)
Lysophosphatidic acid (LPA), a naturally occurring bioactive phospholipid, activates G protein-coupled receptors (GPCRs), leading to regulation of diverse cellular events including cell survival and apoptosis. Despite extensive studies of the signaling pathways that mediate LPA-regulated cell growth and survival, the
Vishal Kumar Gupta et al.
Apoptosis : an international journal on programmed cell death, 25(1-2), 135-150 (2019-12-24)
Lysophosphatidic acid (LPA) is a bioactive lipid, which plays an indispensable role in various physiological and pathological processes. Moreover, an elevated level of LPA has been observed in malignancies of different origins and implicated in their progression via modulation of
Byung-Hwan Lee et al.
Neuroscience letters, 612, 256-260 (2015-12-27)
Ginseng has a long history of use as a tonic for restoration of vigor. One example of ginseng-derived tonic effect is that it can improve physical stamina under conditions of stress. However, the active ingredient and the underlying molecular mechanism
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.
Synthesis of sphingosine analogues: stereoselective synthesis of 3-deoxysphingosine and cis-isomers.
T Kawate et al.
Chemical & pharmaceutical bulletin, 45(12), 2116-2118 (1998-01-20)
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