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Merck

840067C

Avanti

22:6 PS

Avanti Research™ - A Croda Brand

Synonym(s):

1,2-di-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phospho-L-serine (sodium salt); PS(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):
C50H73NO10PNa
CAS Number:
474943-19-6
Molecular Weight:
902.08
UNSPSC Code:
51191904
NACRES:
NA.25

Key Documents

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Product Name

22:6 PS, 1,2-didocosahexaenoyl-sn-glycero-3-phospho-L-serine (sodium salt), chloroform

Assay

>99% (TLC)

form

liquid

packaging

pkg of 1 × 2.5 mL (840067C-25mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 840067C

concentration

10 mg/mL (840067C-25mg)

lipid type

cardiolipins
phospholipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

[H][C@@](COP([O-])(OC[C@](C([O-])=O)([H])[NH3+])=O)(OC(CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)=O)COC(CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)=O.[Na+]

InChI

1S/C50H74NO10P.Na/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-39-41-48(52)58-43-46(44-59-62(56,57)60-45-47(51)50(54)55)61-49(53)42-40-38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2;/h5-8,11-14,17-20,23-26,29-32,35-38,46-47H,3-4,9-10,15-16,21-22,27-28,33-34,39-45,51H2,1-2H3,(H,54,55)(H,56,57);/q;+1/p-1/b7-5-,8-6-,13-11-,14-12-,19-17-,20-18-,25-23-,26-24-,31-29-,32-30-,37-35-,38-36-;/t46-,47+;/m1./s1

InChI key

PRXSBBKPUZKCDC-CHKVJERNSA-M

General description

22:6 PS or 1,2-didocosahexaenoyl-sn-glycero-3-phospho-L-serine is a sodium salt of glycerophospholipid, with substitution of two chains of docosahexaenic acid at the sn-1 and sn-2 positions and phospho-L-serine at the sn-3 position of the glycerol backbone.

Application

22:6 PS or 1,2-didocosahexaenoyl-sn-glycero-3-phospho-L-serine (sodium salt) has been used as an internal lipid standard in lipid extraction by Bligh-Dyer method. It has also been used in liposome preparation to study the effects of the fatty acid (FA) profile of phospholipids on membrane vesiculation by dynamin and endophilin.

Packaging

5 mL Clear Glass Sealed Ampule (840067C-25mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

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

WGK

WGK 3

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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
Peter A Leventis et al.
Annual review of biophysics, 39, 407-427 (2010-03-03)
Phosphatidylserine (PS) is the most abundant negatively charged phospholipid in eukaryotic membranes. PS directs the binding of proteins that bear C2 or gamma-carboxyglutamic domains and contributes to the electrostatic association of polycationic ligands with cellular membranes. Rather than being evenly

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