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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

EU REACH Annex XVII (Restriction List)

CAS No.

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Certificates of Analysis (COA)

Lot/Batch Number
090K5226
066H8386
066H8359
043H84522
039H5189

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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
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
Richard M Epand et al.
Biochemistry, 43(46), 14778-14783 (2004-11-17)
We compared the diacylglycerol kinase (DGK) catalyzed phosphorylation of 1-O-hexanoyl-2-oleoylglycerol (HOG) with 1-O-hexanoyl-2-arachidonoylglycerol (HAG). We assayed the activity of DGKalpha and DGKzeta using a liposomal-based assay system. Liposomal assays show that the DGKalpha and, to a lesser extent, DGKzeta preferentially
M J Pete et al.
Biochimica et biophysica acta, 1299(3), 325-332 (1996-02-16)
Phosphatidylcholine (PC) metabolism was investigated using cytosol (fraction I) and particulate fractions of bovine brain that were enriched with microsomes (fraction II), plasma membranes (fraction III) or mitochondria (fraction IV). Fractions I-III incubated with 1-palmitoyl-2-[14C]arachidonoyl-sn-glycero-3-phosphocholine yielded [14C]arachidonic acid at near
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
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