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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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
J Kötting et al.
Cancer chemotherapy and pharmacology, 30(2), 105-112 (1992-01-01)
Hexadecylphosphocholine (HPC) and octadecylphosphocholine (OPC) show very potent antitumor activity against autochthonous methylnitrosourea-induced mammary carcinomas in rats. The longer-chain and unsaturated homologue erucylphosphocholine (EPC) forms lamellar structures rather than micelles, but nonetheless exhibits antineoplastic activity. Methylnitrosourea was used in the
H Naundorf et al.
Breast cancer research and treatment, 23(1-2), 87-95 (1992-01-01)
The human mammary carcinomas MT-1 and MT-3 originate from surgical material and were transplanted in nude mice. Both tumors have been classified as estradiol- and progesterone receptor-negative. Therapeutic doses of hormones and anti-hormones remained without growth inhibitory effect. MT-1 and
S M Konstantinov et al.
Cancer chemotherapy and pharmacology, 41(3), 210-216 (1998-01-27)
Alkylphosphocholines (APC) represent a new group of ether-lipid-related compounds with remarkable activity against transformed cells in vitro and good tolerability in vivo. Their mechanism of action remains unknown. The aim of the present study was to investigate the effects of
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 115002-5G | 04061833376300 |
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