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Merck

840475P

Avanti

18:1 (Δ9-Cis) PG

Avanti Research™ - A Croda Brand

Synonym(s):

1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1′racglycerol) (sodium salt); DOPG; PG(18:1(9Z)/18:1(9Z))

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About This Item

Empirical Formula (Hill Notation):
C42H78O10PNa
CAS Number:
67254-28-8
Molecular Weight:
797.03
MDL number:
MFCD33403202
UNSPSC Code:
51191904
NACRES:
NA.25

Key Documents

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InChI

1S/C42H79O10P.Na/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(45)49-37-40(38-51-53(47,48)50-36-39(44)35-43)52-42(46)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2;/h17-20,39-40,43-44H,3-16,21-38H2,1-2H3,(H,47,48);/q;+1/p-1/b19-17-,20-18-;/t39?,40-;/m

InChI key

IUVFCFQZFCOKRC-IPKKNMRRSA-M

SMILES string

[H][C@@](COP([O-])(OCC(O)CO)=O)(OC(CCCCCCC/C=C\CCCCCCCC)=O)COC(CCCCCCC/C=C\CCCCCCCC)=O.[Na+]

description

1,2-dioleoyl-sn-glycero-3-phospho-(1′-rac-glycerol) (sodium salt)

assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 1 g (840475P-1g), pkg of 2 × 100 mg (840475P-200mg), pkg of 5 × 100 mg (840475P-500mg), pkg of 1 × 25 mg (840475P-25mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand

lipid type

cardiolipins
phospholipids

shipped in

dry ice

storage temp.

−20°C

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General description

Phosphoglyceride (PG) are also referred as glycerophospholipid. It is an important component of membrane bilayers. It has three-carbon backbone of glycerol, two long-chain fatty acids, esterified to hydroxyl groups on carbons 1 and 2 of the glycerol and phosphoric acid esterified to the C3 hydroxyl group of glycerol. It is found at high levels in the membranes of all cells and at low levels in fat stores. 1,2-dioleoyl-sn-glycero-3-phospho-(1′-rac-glycerol) (DOPG)/18:1 (Δ9-Cis) PG has two hydroxyl groups in its head group. It is an anionic lipid.

Application

18:1 (Δ9-Cis) PG has been used:
  • in the preparation of giant unilamellar vesicle (GUV)
  • in the preparation 200 nm large unilamellar vesicles (LUV)
  • as a supplement in native macrophage membranes to generate membrane liposomes with an artificially modified electrical charge

Biochem/physiol Actions

Phosphoglycerides (PG)/glycerophospholipids play a key role in cell signaling systems. It also serves as an anchor for proteins in cell membranes.

Packaging

5 mL Clear Glass Sealed Ampule (840475P-200mg)
5 mL Clear Glass Sealed Ampule (840475P-25mg)
5 mL Clear Glass Sealed Ampule (840475P-500mg)
60 mL Amber Wide Mouth Screw Cap Glass Bottle (840475P-1g)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Membrane Structure and Dynamics
Cell Biology, 227- 239 (2017)
Using protein-fatty acid complexes to improve vitamin D stability
Pedersen JN, et al.
Journal of Dairy Science, 99(10), 7755-7767 (2016)
Tripartite Chimeras Comprising Functional Domains Derived from the Cytosolic NADPH Oxidase Components p47phox, p67phox, and Rac1 Elicit Activator-independent Superoxide Production by Phagocyte Membranes AN ESSENTIAL ROLE FOR ANIONIC MEMBRANE PHOSPHOLIPIDS
Berdichevsky Y, et al.
The Journal of biological chemistry, 282(30), 22122- 22139 (2007)
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