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Merck
CN

P4203

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

lyophilized powder

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
UNSPSC Code:
51191904
PubChem Substance ID:
329820202
MDL number:
MFCD00171671

Key Documents

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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

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 key

PUDHBQQGURLBGJ-IVFHWKNFSA-N

assay

≥95% (TLC), ≥97% (GC)

form

lyophilized powder

functional group

phospholipid

lipid type

phosphoglycerides

shipped in

ambient

storage temp.

−20°C

Quality Level

200

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Packaging

Packaged under Argon.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
110M5208
048K5204
065K5208
100K5240
087H8027

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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
N Leitinger et al.
Advances in experimental medicine and biology, 433, 379-382 (1997-01-01)
Our group has previously demonstrated that oxidized phospholipids derived from mildly oxidized low density lipoprotein (MM-LDL) or oxidized 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphorylcholine (oxPAPC) increase monocyte-endothelial interactions. There are indications that the effects of these phospholipids are receptor mediated. Oxidized phospholipids have previously been
S Paglin et al.
The Journal of biological chemistry, 268(16), 11697-11702 (1993-06-05)
Hormonally regulated and particulate-associated phospholipase A2 (PLA2) was detected in endothelial cells from bovine pulmonary artery. The enzyme was solubilized and subjected to initial characterization. PLA2 activity was determined in subcellular fractions from bradykinin (BK)-stimulated and nonstimulated cells by following
A E Drobnies et al.
Biochemistry, 38(47), 15606-15614 (1999-11-26)
The enzyme CTP:phosphocholine cytidylyltransferase (CT) binds reversibly to membranes and is active only in its membrane-bound form. Membrane lipid composition influences the equilibrium between its soluble and membrane-bound forms. Whereas the enzyme is not activated by phosphatidylcholine (PC) vesicles, it
N Khaselev et al.
Journal of lipid research, 41(4), 564-572 (2000-04-01)
Plasmenyl phospholipids are a structurally unique class of lipids that contain a vinyl ether substituent at the sn-1 position of the glycerol backbone, imparting unique susceptibility to oxidative reactions that may take place at the cell membrane lipid bilayer. Several
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