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P6412

Sigma-Aldrich

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

≥99%

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Synonym(s):
1,2-Ditetradecanoyl-sn-glycero-3-phospho-(1′-rac-glycerol) sodium salt, L-α-Phosphatidyl-DL-glycerol, dimyristoyl, L-α-Phosphatidyl-DL-glycerol, dimyristoyl sodium salt, DMPG, DMPG-Na, PG(14:0/14:0), Tetradecanoic acid 1-[[[(2,3-dihydroxypropoxy)hydroxyphosphinyl]oxy]methyl]-1,2-ethanediyl ester monosodium salt
Linear Formula:
C34H66O10PNa
CAS Number:
200880-40-6
Molecular Weight:
688.85
MDL number:
MFCD00056649
UNSPSC Code:
12352211
PubChem Substance ID:
24898765
NACRES:
NA.25

biological source

synthetic (organic)

Quality Level

200

Assay

≥99%

form

powder

functional group

ester

lipid type

phosphoglycerides

shipped in

ambient

storage temp.

−20°C

SMILES string

[H][C@@](COP([O-])(OCC(O)CO)=O)(OC(CCCCCCCCCCCCC)=O)COC(CCCCCCCCCCCCC)=O.[Na+]

InChI

1S/C34H67O10P.Na/c1-3-5-7-9-11-13-15-17-19-21-23-25-33(37)41-29-32(30-43-45(39,40)42-28-31(36)27-35)44-34(38)26-24-22-20-18-16-14-12-10-8-6-4-2;/h31-32,35-36H,3-30H2,1-2H3,(H,39,40);/q;+1/p-1/t31?,32-;/m1./s1

InChI key

QLNOOKSBAYIHQI-SKZICHJRSA-M

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General description

1,2-Dimyristoyl-sn-glycero-3-phospho-rac-(1-glycerol) sodium salt (DMPG) is a 14C atoms containing anionic saturated phospholipid. It is predominantly present in the gram-positive bacterial membranes and comprises two chains. To mimic bacterial membranes, DMPG is combined with zwitterionic phospholipids. At low salt, DMPG forms leaky vesicles in gel and fluid phases. It displays gel−fluid transition at high salt. DMPG is used as a model system for peptide−lipid interaction studies and in temperature based membrane structural studies.

Application

1,2-Dimyristoyl-sn-glycero-3-phospho-rac-(1-glycerol) sodium salt has been used as an internal standard in reverse phase high performance liquid chromatography(RP-HPLC). It has also been used as a component of foam films (FFs) for diffusion studies.
Prototype for the preparation of liposomes with negatively charged hydrophilic head groups. Phase transitions, close-packing ratios, and ion permeability are all strongly affected by the presence of a stoichiometric amount (1:2) of divalent cations.

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Pricing

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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The peculiar thermo-structural behavior of the anionic lipid DMPG
Lamy-Freund MT and Riske KA
Chemistry and Physics of Lipids, 122(1-2), 19-32 (2003)
Aqueous dispersions of DMPG in low salt contain leaky vesicles
Barroso RP, et al.
Chemistry and Physics of Lipids, 165(2), 169-177 (2012)
Molecular mobility in the monolayers of foam films stabilized by porcine lung surfactant
Lalchev ZI, et al.
Biophysical Journal, 71(5), 2591-2601 (1996)
Effects of pure n-alkanes and crude oil on bacterial phospholipid classes and molecular species determined by electrospray ionization mass spectrometry
Mazzella N, et al.
Journal of Chromatography. B, Biomedical Sciences and Applications, 822(1-2), 40-53 (2005)
Nicolas Bertram et al.
Langmuir : the ACS journal of surfaces and colloids, 31(30), 8386-8391 (2015-07-15)
Nanodisc films are a promising approach to study the equilibrium conformation of membrane bound proteins in native-like environment. Here we compare nanodisc formation for NADPH-dependent cytochrome P450 oxidoreductase (POR) using two different scaffold proteins, MSP1D1 and MSP1E3D1. Despite the increased
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