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845875P

Avanti

18:1 Lyso PC

Avanti Research - A Croda Brand

Synonym(s):

1--(9Z-octadecenoyl)-sn-glycero-3-phosphocholine; PC(18:1(9Z)/0:0); 110688

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About This Item

Empirical Formula (Hill Notation):
C26H52NO7P
CAS Number:
Molecular Weight:
521.67
UNSPSC Code:
51191904
NACRES:
NA.25

description

1-oleoyl-2-hydroxy-sn-glycero-3-phosphocholine

Assay

>99% (LPC; may contain up to 10% of the 2-LPC isomer, TLC)

form

powder

packaging

pkg of 2 × 100 mg (845875P-200mg)
pkg of 5 × 100 mg (845875P-500mg)
pkg of 1 × 25 mg (845875P-25mg)

manufacturer/tradename

Avanti Research - A Croda Brand

shipped in

dry ice

storage temp.

−20°C

SMILES string

O[C@](COP([O-])(OCC[N+](C)(C)C)=O)([H])COC(CCCCCCC/C=C\CCCCCCCC)=O

InChI

1S/C26H52NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)32-23-25(28)24-34-35(30,31)33-22-21-27(2,3)4/h12-13,25,28H,5-11,14-24H2,1-4H3/b13-12-/t25-/m1/s1

InChI key

YAMUFBLWGFFICM-PTGWMXDISA-N

General description

Lysophosphatidylcholine (LPC) is a lysophospholipid mediator. This bioactive proinflammatory lipid is produced by pathological activities. It is one of the important constituent of oxidized low-density lipoprotein (Ox-LDL).

Application

18:1 Lyso PC is suitable for use as a lysophospholipid mediator to compare the effect of sphingosylphosphorylcholine (SPC). It has been used as a supplement in Yeast nitrogen base (YNB) medium to rescue choline auxotrophy.

Biochem/physiol Actions

Lysophosphatidylcholine (LPC) participates as a key factor in the atherogenic activity of oxidized low-density lipoprotein (Ox-LDL). It alters the roles in endothelial cells, smooth muscle cells, monocytes, macrophages, T-cells, thereby involving in atherosclerosis and inflammatory diseases. LPC activates protein kinase C, extracellular-signal-regulated kinases, protein tyrosine kinases, and Ca(2+), that are second messengers.

Packaging

5 mL Clear Glass Sealed Ampule (845875P-200mg)
5 mL Clear Glass Sealed Ampule (845875P-25mg)
5 mL Clear Glass Sealed Ampule (845875P-500mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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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Overproduction of phospholipids by the Kennedy Pathway Leads to Hypervirulence in Candida albicans
Tams RN, et al.
Frontiers in Microbiology, 10(2), 86-86 (2019)
Lysophospholipid receptors: signalling, pharmacology and regulation by lysophospholipid metabolism
zu HDM and Jakobs KH
Biochimica et Biophysica Acta - Biomembranes, 1768(4), 923-940 (2007)
Regulation of ryanodine receptors by sphingosylphosphorylcholine: Involvement of both calmodulin-dependent and-independent mechanisms
Kovacs E, et al.
Biochemical and biophysical research communications, 401(2), 281-286 (2010)
Jacinto López-Sagaseta et al.
The EMBO journal, 31(8), 2047-2059 (2012-03-08)
Invariant Natural Killer T (iNKT) cells use highly restricted αβ T cell receptors (TCRs) to probe the repertoire of lipids presented by CD1d molecules. Here, we describe our studies of lysophosphatidylcholine (LPC) presentation by human CD1d and its recognition by
Ieva Ailte et al.
Scientific reports, 6, 30336-30336 (2016-07-28)
Shiga toxin (Stx), an AB5 toxin, binds specifically to the neutral glycosphingolipid Gb3 at the cell surface before being transported into cells. We here demonstrate that addition of conical lysophospholipids (LPLs) with large head groups inhibit Stx binding to cells

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