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P0319

Sigma-Aldrich

2-Arachidonoyl-1-palmitoyl-sn-glycero-3-phosphocholine

10 mg/mL in chloroform

Synonym(s):

PC, 1-Hexadecanoyl-2-([cis,cis,cis,cis]-5,8,11,14-eicosatetraenoyl)-sn-glycero-3-phosphocholine, L-α-Phosphatidylcholine, β-arachidonoyl-γ-palmitoyl

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About This Item

Empirical Formula (Hill Notation):
C44H80NO8P
CAS Number:
35418-58-7
Molecular Weight:
782.08
MDL number:
MFCD00171671
UNSPSC Code:
12352211
PubChem Substance ID:
329820031

concentration

10 mg/mL in chloroform

functional group

phospholipid

shipped in

dry ice

storage temp.

−20°C

SMILES string

CCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)COP([O-])(=O)OCC[N+](C)(C)C

InChI

1S/C44H80NO8P/c1-6-8-10-12-14-16-18-20-21-22-23-25-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-24-19-17-15-13-11-9-7-2/h14,16,20-21,23,25,28,30,42H,6-13,15,17-19,22,24,26-27,29,31-41H2,1-5H3/b16-14-,21-20-,25-23-,30-28-/t42-/m1/s1

InChI key

PUDHBQQGURLBGJ-IVFHWKNFSA-N

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Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 1 - STOT SE 3

Target Organs

Central nervous system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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A S Bowman et al.
Experimental parasitology, 87(2), 121-132 (1997-10-27)
Saliva from female lone star ticks, Amblyomma americanum, contained a novel phospholipase A2 (PLA2) activity that hydrolyzed 14C-arachidonate from 14C-arachidonyl phosphatidylcholine. The tick saliva PLA2 (ts-PLA2) was active over a broad pH range (4.5-11.5) with two distinct pH optima of
F Ghomashchi et al.
Biochemistry, 31(15), 3814-3824 (1992-04-21)
The kinetics of hydrolysis of 1-palmitoyl-2-arachidonyl-sn-glycero-3-phosphocholine vesicles catalyzed by the high molecular weight phospholipase A2 from rat kidney show an anomalous behavior. The reaction progress lasts for several minutes and then stops after only 5-10% of the available substrate has
A D Watson et al.
The Journal of biological chemistry, 272(21), 13597-13607 (1997-05-23)
Entry of monocytes into the vessel wall is an important event in atherogenesis. Previous studies from our laboratory suggest that oxidized arachidonic acid-containing phospholipids present in mildly oxidized low density lipoproteins (MM-LDL) can activate endothelial cells to bind monocytes. In
Sae-A Lee et al.
Biochemical and biophysical research communications, 408(1), 132-138 (2011-04-06)
Peptidoglycan (PG) is detected in a high proportion in inflammatory cell-rich regions of human atheromatous plaques. In the present study, we determined the cellular factors involved in PG-mediated chemokine expression in mononuclear cells in order to understand the molecular mechanisms
N Leitinger et al.
Proceedings of the National Academy of Sciences of the United States of America, 96(21), 12010-12015 (1999-10-16)
We previously have demonstrated that oxidized 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphorylcholine (OxPAPC), a component of minimally modified low density lipoprotein (MM-LDL), activates endothelial cells to bind monocytes. 1-Palmitoyl-2- (5-oxovaleroyl)-sn-glycero-3-phosphorylcholine (POVPC) and 1- palmitoyl-2-glutaroyl-sn-glycero-3-phosphorylcholine (PGPC), which are present in OxPAPC, MM-LDL, and atherosclerotic lesions, were
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