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SMB00611

Sigma-Aldrich

1,2-Dilauroyl-sn-glycero-3-phosphorylglycerol sodium salt

≥98%

Synonym(s):

1,2-Didodecanoyl-sn-glycero-3-phosphorylglycerol sodium, 1-[[[(2,3-Dihydroxypropoxy)hydroxyphosphinyl]oxy]methyl]-1,2-ethanediyl ester-dodecanoic acid sodium

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About This Item

Empirical Formula (Hill Notation):
C30H58O10PNa
CAS Number:
73548-69-3
Molecular Weight:
632.74
UNSPSC Code:
12352211
PubChem Substance ID:
329825078
NACRES:
NA.25

assay

≥98%

form

powder

functional group

carboxylic acid

lipid type

phosphoglycerides

shipped in

wet ice

storage temp.

−20°C

InChI

1S/C30H59O10P.Na/c1-3-5-7-9-11-13-15-17-19-21-29(33)37-25-28(26-39-41(35,36)38-24-27(32)23-31)40-30(34)22-20-18-16-14-12-10-8-6-4-2;/h27-28,31-32H,3-26H2,1-2H3,(H,35,36);/q;+1/p-1/t27-,28+;/m0./s1

InChI key

CIRSYGHBBDDURM-DUZWKJOOSA-M

Biochem/physiol Actions

In nature, phosphatidylglycerol is a ubiquitous phospholipid that has specialized structural and functional properties in membranes. Although rare in mammalian membranes, it is highly prevalent in thylakoid membranes of cyanobacteria and higher plants, and it plays a role in photosynthesis. Phosphatidylglycerol may also have a role in bioactive sphingolipid signaling.

Phosphatidylglycerols are used in in silico studies of model membranes. Under specific experimental conditions, they exhibit similar phase transition properties as zwitterionic phosphatidylcholines. Lipid-based particle drug delivery studies using dispersions of dilauroylphosphatidylethanolamine (DLPE) and dilauroylphosphatidylglycerol (DLPG) have been shown to exhibit a metastable state which allows for the manipulation of delayed nucleation; thus providing new avenues in the design of novel modalities for the drug delivery of therapeutic payloads.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Guy Jacoby et al.
Scientific reports, 5, 9481-9481 (2015-03-31)
The metastable-to-stable phase-transition is commonly observed in many fields of science, as an uncontrolled independent process, highly sensitive to microscopic fluctuations. In particular, self-assembled lipid suspensions exhibit phase-transitions, where the underlying driving mechanisms and dynamics are not well understood. Here
Silvia Vaena de Avalos et al.
The Journal of biological chemistry, 280(8), 7170-7177 (2004-12-22)
Inositolsphingolipid phospholipase C (Isc1p) is the Saccharomyces cerevisiae member of the extended family of neutral sphingomyelinases that regulates the generation of bioactive ceramides. Recently, we reported that Isc1p is post-translationally activated in the post-diauxic phase of growth and that it
R M Epand et al.
Biophysical journal, 63(2), 327-332 (1992-08-01)
Dilauroyl and dimyristoylphosphatidylglycerol (DMPG) form a more stable gel state when aqueous suspensions are incubated several days at low temperature (0-2 degrees C), pH 7.4 with 0.15 M NaCl. This gel state is characterized by a higher transition temperature and
Jianjun Pan et al.
Biochimica et biophysica acta, 1818(9), 2135-2148 (2012-05-16)
We have determined the molecular structures of commonly used phosphatidylglycerols (PGs) in the commonly accepted biologically relevant fluid phase. This was done by simultaneously analyzing small angle neutron and X-ray scattering data, with the constraint of measured lipid volumes. We

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