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Key Documents

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:
Molecular Weight:
435.62
Beilstein:
3694312
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
Pricing and availability is not currently available.

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[1], induces apoptosis in three human leukemic cell lines[2].

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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B B Lundberg
Anti-cancer drug design, 12(6), 503-513 (1997-10-06)
This study investigated the relevance of combining lipophilic anti-cancer drugs intercalated into the phospholipid bilayer of liposomes. The cytotoxic interaction of two ether lipids, octadecylphosphocholine and ET-18-OCH3, and the chemotherapeutic drugs teniposide and paclitaxel on cancer cells in vitro was
J D Hille et al.
Biochemistry, 20(14), 4068-4073 (1981-07-07)
Porcine pancreatic phospholipase A2 interacts with micelles of the substrate analogue n-octadecylphosphocholine to form a specific complex over considerably wide concentration ranges of both lipid and protein. UV absorption difference spectroscopy measurements indicate that the ratio of lipid to protein
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
James McBride et al.
Journal of clinical microbiology, 43(2), 629-634 (2005-02-08)
We have developed and optimized a 96-well microtiter plate assay, based on the reduction of alamarBlue, to assess the efficacies of much needed new antimicrobials against Acanthamoeba species. This assay has been optimized for determination of drug efficacy against two
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

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