04449
O-(Octadecylphosphoryl)choline
≥98% (TLC)
Synonym(s):
Octadecylphosphocholine, Phosphocholine octadecyl ester
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About This Item
Empirical Formula (Hill Notation):
C23H50NO4P
CAS Number:
Molecular Weight:
435.62
PubChem Substance ID:
UNSPSC Code:
12352211
Beilstein/REAXYS Number:
3694312
MDL number:
assay
≥98% (TLC)
lipid type
phospholipids
storage temp.
−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
InChI key
ZBNJXSZNWZUYCI-UHFFFAOYSA-N
Application
Antitumor phospholipid, induces apoptosis in three human leukemic cell lines.
Biochem/physiol Actions
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.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Storage Class
13 - Non Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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
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
New cytostatics with experimentally different toxic profiles.
M R Berger et al.
Cancer treatment reviews, 14(3-4), 307-317 (1987-12-01)
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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 115002-5G | 04061833376300 |
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