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04449

Sigma-Aldrich

O-(Octadecylphosphoryl)-cholin

≥98% (TLC)

Synonym(e):

Octadecylphosphocholin, Phosphocholin-octadecylester

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About This Item

Empirische Formel (Hill-System):
C23H50NO4P
CAS-Nummer:
65956-63-0
Molekulargewicht:
435.62
Beilstein:
3694312
MDL-Nummer:
MFCD00171405
UNSPSC-Code:
12352211
PubChem Substanz-ID:
329747927

Assay

≥98% (TLC)

Lipid-Typ

phospholipids

Lagertemp.

−20°C

SMILES String

CCCCCCCCCCCCCCCCCCOP([O-])(=O)OCC[N+](C)(C)C

InChI

1S/C23H50NO4P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-22-27-29(25,26)28-23-21-24(2,3)4/h5-23H2,1-4H3

InChIKey

ZBNJXSZNWZUYCI-UHFFFAOYSA-N

Anwendung

Antitumor phospholipid, induces apoptosis in three human leukemic cell lines.

Biochem./physiol. Wirkung

C18-phosphocholine was the most potent alkylphosphocholine tested in inhibiting phosphatidylcholine biosynthesis. The effect is mediated by interrupting the translocation of the rate-limiting enzyme, CTP:phosphocholine cytidylyltransferase, to membranes, where it is active.

Verpackung

Bottomless glass bottle. Contents are inside inserted fused cone.

Lagerklassenschlüssel

13 - Non Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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M K Jain et al.
Biochimica et biophysica acta, 813(1), 68-76 (1985-02-28)
Properties of the aqueous dispersions of n-octadecylphosphocholine are examined by differential scanning calorimetry, fluorescence depolarization, light scattering, 31P-NMR, pig pancreatic phospholipase A2 binding, and X-ray diffraction. On heating, these dispersions exhibit a sharp lamellar to micelle transition at 20.5 degrees
N Dittrich et al.
Journal of enzyme inhibition, 11(1), 67-75 (1996-08-01)
Alkylphosphate esters were shown to be potent inhibitors of phospholipase D. Using phosphatidyl choline/sodium dodecylsulfate (2:1) as substrate, IC50 values were determined for alkylphosphocholines of different chain length (C10-C18) and for various octadecylphosphate esters with different polar head groups. The
E Posse de Chaves et al.
The Biochemical journal, 312 ( Pt 2), 411-417 (1995-12-01)
At least 50% of the major axonal membrane lipid, phosphatidylcholine, of rat sympathetic neurons is synthesized in situ in axons [Posse de Chaves, Vance, Campenot and Vance (1995) J. Cell Biol. 128, 913-918]. In the same study we reported that
New cytostatics with experimentally different toxic profiles.
M R Berger et al.
Cancer treatment reviews, 14(3-4), 307-317 (1987-12-01)
Janez Mravljak et al.
Journal of medicinal chemistry, 48(20), 6393-6399 (2005-09-30)
Alkylphospholipid analogues of perifosine and miltefosine bearing a nitroxide moiety at different positions on an alkyl chain were synthesized as electron paramagnetic resonance (EPR) probes. Their amphiphilic properties were characterized by determining their critical micelle concentration (cmc) and hemolytic activity
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