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Merck
CN

850400C

Avanti

22:6 (Cis) PC

Avanti Research™ - A Croda Brand

Synonym(s):

1,2-di-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine; PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))

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About This Item

Empirical Formula (Hill Notation):
C52H80NO8P
CAS Number:
99296-81-8
Molecular Weight:
878.17
MDL number:
MFCD00674317
UNSPSC Code:
51191904
NACRES:
NA.25

Key Documents

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Product Name

22:6 (Cis) PC, 1,2-didocosahexaenoyl-sn-glycero-3-phosphocholine, chloroform

SMILES string

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

InChI

1S/C52H80NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-42-44-51(54)58-48-50(49-60-62(56,57)59-47-46-53(3,4)5)61-52(55)45-43-41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h8-11,14-17,20-23,26-29,32-35,38-41,50H,6-7,12-13,18-19,24-25,30-31,36-37,42-49H2,1-5H3/b10-8-,11-9-,16-14-,17-15-,22-20-,23-21-,28-26-,29-27-,34-32-,35-33-,40-38-,41-39-/t50-/m1/s1

InChI key

XLKQWAMTMYIQMG-SVUPRYTISA-N

assay

>99% (TLC)

form

liquid

packaging

pkg of 1 × 2.5 mL (850400C-25mg)
pkg of 5 × 4 mL (850400C-500mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 850400C

concentration

10 mg/mL (850400C-25mg)
25 mg/mL (850400C-500mg)

lipid type

cardiolipins
phospholipids

shipped in

dry ice

storage temp.

−20°C

Application

22:6 (cis) PC or 1,2-didocosahexaenoyl-sn-glycero-3-phosphocholine might be used:
  • in liposomes, to study its effect on membrane vesiculation by dynamin and endophilin
  • in multi-lamellar vesicles (MLVs) to analyze its effect on the biophysical properties of lipid membranes and on its interaction with a fragment of the Aβ peptide
  • in lipid bilayers to study the influence of cholesterol on lateral segregation of saturated and unsaturated phospholipids

General description

22:6 (cis) PC or 1,2-didocosahexaenoyl-sn-glycero-3-phosphocholine is an unsaturated glycerophospholipid, with substitution of two chains of docosahexaenic acid at sn-1 and sn-2 positions of the glycerol backbone, along with choline as a headgroup. It is an omega-3 lipid.

Packaging

5 mL Clear Glass Sealed Ampule (850400C-25mg)
5 mL Clear Glass Sealed Ampule (850400C-500mg)

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 - Aquatic Chronic 3 - Carc. 2 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 1 - STOT SE 3

target_organs

Central nervous system, Liver,Kidney

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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Oskar Engberg et al.
Biophysical journal, 111(3), 546-556 (2016-08-11)
Saturated and unsaturated phospholipids (PLs) can segregate into lateral domains. The preference of cholesterol for saturated acyl chains over monounsaturated, and especially polyunsaturated ones, may also affect lateral segregation. Here we have studied how cholesterol influenced the lateral segregation of
Giuseppe Vitiello et al.
Langmuir : the ACS journal of surfaces and colloids, 29(46), 14239-14245 (2013-10-23)
Polyunsaturated omega-3 fatty acids are increasingly proposed as dietary supplements able to reduce the risk of development or progression of the Alzheimer's disease (AD). To date, the molecular mechanism through which these lipids act has not been yet univocally identified.
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
Philippe Calvez et al.
Journal of the American Chemical Society (2016-10-01)
Recoverin undergoes a calcium-myristoyl switch during visual phototransduction. Indeed, calcium binding by recoverin results in the extrusion of its myristoyl group, which allows its membrane binding. However, the contribution of particular lipids and of specific amino acids of recoverin in

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