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P6412

Sigma-Aldrich

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

≥99%

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

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About This Item

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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Storage Class

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flash_point_f

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flash_point_c

Not applicable

ppe

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Certificates of Analysis (COA)

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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)
Molecular mobility in the monolayers of foam films stabilized by porcine lung surfactant
Lalchev ZI, et al.
Biophysical Journal, 71(5), 2591-2601 (1996)
Aqueous dispersions of DMPG in low salt contain leaky vesicles
Barroso RP, et al.
Chemistry and Physics of Lipids, 165(2), 169-177 (2012)
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)
Matthew G K Benesch et al.
Biochimica et biophysica acta, 1848(11 Pt A), 2878-2888 (2015-08-16)
The thermotropic phase behavior and organization of model membranes composed of binary mixtures of the quadruple-chained, nominally dianionic phospholipid tetramyristoylcardiolipin (TMCL) with the double-chained, monoanionic phospholipid dimyristoylphosphatidylglycerol (DMPG) were examined by differential scanning calorimetry (DSC) and Fourier-transform infrared (FTIR) spectroscopy.
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