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845875P

Avanti

18:1 Lyso PC

Avanti Polar Lipids

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Synonym(s):
1--(9Z-octadecenoyl)-sn-glycero-3-phosphocholine; PC(18:1(9Z)/0:0); 110688
Empirical Formula (Hill Notation):
C26H52NO7P
CAS Number:
19420-56-5
Molecular Weight:
521.67
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 Polar Lipids

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

Related Categories

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)

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Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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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
Sobhan Roy et al.
Proceedings of the National Academy of Sciences of the United States of America, 111(43), E4648-E4657 (2014-10-10)
CD1c is a member of the group 1 CD1 family of proteins that are specialized for lipid antigen presentation. Despite high cell surface expression of CD1c on key antigen-presenting cells and the discovery of its mycobacterial lipid antigen presentation capability
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