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O9262

Sigma-Aldrich

1-O-Octadecyl-2-O-methyl-sn-glycero-3-phosphorylcholine

≥99% (TLC), waxy solid

Synonym(s):

ET-18-OCH3

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About This Item

Empirical Formula (Hill Notation):
C27H58NO6P
Molecular Weight:
523.73
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77

assay

≥99% (TLC)

form

waxy solid

color

white

solubility

ethanol: soluble 15 mg/mL at 45 °C
chloroform: soluble >25 mg/mL
DMSO: soluble

shipped in

wet ice

storage temp.

−20°C

SMILES string

[O-]P(OCC[N+](C)(C)C)(OC[C@]([H])(OC)COCCCCCCCCCCCCCCCCCC)=O

InChI

1S/C27H58NO6P/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-23-32-25-27(31-5)26-34-35(29,30)33-24-22-28(2,3)4/h27H,6-26H2,1-5H3/t27-/m1/s1

InChI key

MHFRGQHAERHWKZ-HHHXNRCGSA-N

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Biochem/physiol Actions

Phosphoinositide-specific phospholipase C (PI-PLC) inhibitor.

Features and Benefits

This compound is featured on the Phospholipase C page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Preparation Note

1-O-Octadecyl-2-O-methyl-sn-glycero-3- phosphorylcholine is soluble in ethanol at 15 mg/ml and in chloroform at 25 mg/ml.
The following steps are for the preparation of a DMSO stock solution.
1. Solubilize 1-O-Octadecyl-2-O-methyl-sn-glycero-3-phosphorylcholine in chloroform.
2. Deposit a thin film of the compound on the sides of a container by evaporating the chloroform with a stream of nitrogen or argon.
3. Add DMSO and vortex mix to dissolve the compound from the sides of the container. The DMSO or ethanol solutions may be diluted at least 1000-fold directly into stirred aqueous cell culture medium.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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I Baburina et al.
The Journal of biological chemistry, 273(4), 2169-2173 (1998-01-27)
A HeLa cell line was constructed for the regulation of CTP:phosphocholine cytidylyltransferase (CCT) expression via a tetracycline-responsive promoter to test the role of CCT in apoptosis triggered by exposure of cells to the antineoplastic phospholipid 1-O-octadecyl-2-O-methyl-rac-glycero-3-phosphocholine (ET-18-OCH3). Basal CCT expression
Kei Tamura et al.
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