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:
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
assay
≥98% (TLC)
lipid type
phospholipids
storage temp.
−20°C
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
Regulatory Information
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New cytostatics with experimentally different toxic profiles.
M R Berger et al.
Cancer treatment reviews, 14(3-4), 307-317 (1987-12-01)
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
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
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
M R Berger et al.
Journal of cancer research and clinical oncology, 119(9), 541-548 (1993-01-01)
Alkylphosphocholines, and especially their main representative hexadecylphosphocholine (HPC), show high anticancer activity in methylnitrosourea (MNU)-induced autochthonous rat mammary carcinoma. The regression of MNU-induced rat mammary carcinoma during HPC treatment can be evaluated by computed tomography and sonography. This allows a
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