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Merck
CN

850397C

Avanti

20:4 (Cis) PC

Avanti Research™ - A Croda Brand

Synonym(s):

1,2-di-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine; DAPC; PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))

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About This Item

Empirical Formula (Hill Notation):
C48H80NO8P
CAS Number:
17688-29-8
Molecular Weight:
830.12
MDL number:
MFCD00171670
UNSPSC Code:
51191904
NACRES:
NA.25

Key Documents

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Product Name

20:4 (Cis) PC, 1,2-diarachidonoyl-sn-glycero-3-phosphocholine, chloroform

SMILES string

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

InChI

1S/C48H80NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-47(50)54-44-46(45-56-58(52,53)55-43-42-49(3,4)5)57-48(51)41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h14-17,20-23,26-29,32-35,46H,6-13,18-19,24-25,30-31,36-45H2,1-5H3/b16-14-,17-15+,22-20-,23-21-,28-26-,29-27-,34-32-,35-33-/t46-/m1/s1

InChI key

LZLVZIFMYXDKCN-HLKGGLNDSA-N

assay

>99% (TLC)

form

liquid

packaging

pkg of 1 × 2.5 mL (850397C-25mg)
pkg of 2 × 4 mL (850397C-200mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 850397C

concentration

10 mg/mL (850397C-25mg)
25 mg/mL (850397C-200mg)

lipid type

cardiolipins
phospholipids

shipped in

dry ice

storage temp.

−20°C

Application

20:4 (cis) PC or 1,2-diarachidonoyl-sn-glycero-3-phosphocholine might be used:
  • in lipid bilayer, to study its effect on membrane vesiculation by dynamin and endophilin
  • as a phosphatidylcholine (PC) standard to compare the extraction efficiency of the three tested solvent systems prior to liquid chromatography electrospray ionization tandem mass spectrometry (LC-ESI-MS/MS) analysis
  • in low density lipid (LDL)-mimicking liposome as an alternative to LDL for evaluating the LDL-oxidation preventing antioxidants

General description

20:4 (cis) PC or 1,2-diarachidonoyl-sn-glycero-3-phosphocholine is an unsaturated glycerophospholipid, with substitution of two chains of arachidonic acid at sn-1 and sn-2 positions of the glycerol backbone, along with choline as a headgroup.
The list of Phosphatidylcholine products offered by Avanti is designed to provide compounds having a variety of physical properties. Products available include short chain (C3-C8 are water soluble and hygroscopic), saturated, multi-unsaturated and mixed acid PC′s. All of the products are purified by HPLC, and special precautions are taken to protect the products for oxidization and hydrolysis.

Packaging

5 mL Clear Glass Sealed Ampule (850397C-200mg)
5 mL Clear Glass Sealed Ampule (850397C-25mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

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

target_organs

Liver,Kidney, Respiratory system

Storage Class

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

wgk

WGK 3

flash_point_f

does not flash

flash_point_c

does not flash

Regulatory Information

危险化学品
易制毒化学品（2类）
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Seiji Takeda et al.
Biochemical and biophysical research communications, 513(1), 275-279 (2019-04-08)
Oxidation of low-density lipoproteins (LDL) causes atherosclerosis. Detection of oxidation of LDL-mimetic liposomes using an electrode might serve as a convenient tool in the search of antioxidants for the prevention of atherosclerosis. This report proposes a reaction mechanism between LDL-mimetic
Ana Gonzálvez et al.
Analytical and bioanalytical chemistry, 396(8), 2965-2975 (2010-02-27)
A zirconia (ZrO(2))-modified solid-phase extraction sorbent has been evaluated for selective extraction of phosphatidylcholines from biological samples, followed by analysis of the isolated solutes by reversed-phase liquid chromatography-electrospray ionization-tandem mass spectrometry. The clean-up process was optimized using seven standard phosphatidylcholines
Marco M Manni et al.
eLife, 7 (2018-03-16)
Phospholipid membranes form cellular barriers but need to be flexible enough to divide by fission. Phospholipids generally contain a saturated fatty acid (FA) at position sn1 whereas the sn2-FA is saturated, monounsaturated or polyunsaturated. Our understanding of the impact of

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