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04449

Sigma-Aldrich

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:
65956-63-0
Molecular Weight:
435.62
Beilstein:
3694312
MDL number:
MFCD00171405
UNSPSC Code:
12352211
PubChem Substance ID:
329747927

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 Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCBF0098V
BCBC1875V
BCBC1875

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R Zeisig et al.
Anti-cancer drugs, 2(4), 411-417 (1991-08-01)
Hexadecylphosphocholine (HPC) and its analogs with a longer alkyl chain (C18 and C20) were examined for antineoplastic activity in the murine tumor models P388 leukemia, B 16 melanoma, the mammary carcinoma C3H and Ca 755, and the human MT-1 mammary
V Brochez et al.
Lipids, 34(5), 511-516 (1999-06-24)
The determination of cellular content of octadecylphosphocholine (D-19391) and hexadecylphosphocholine (HePC, D-18506), two anticancer agents of the alkylphosphocholine group, using capillary gas chromatography is described. The compounds' cytotoxicity was first determined by the MTT [3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyltetrazolium] assay, being indicative for 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
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 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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