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P6412

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
NACRES:
NA.25
PubChem Substance ID:
24898765
UNSPSC Code:
12352211
MDL number:
MFCD00056649
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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

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
SLCH8374
SLCG5302
SLBW8632
SLBS0901V
SLBF3193V

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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)
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)
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Global Trade Item Number

SKUGTIN
P6412-100MG04061832797014
P6412-25MG04061834393368
P6412-500MG04061834393375