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Merck
CN

O9262

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
NACRES:
NA.77
PubChem Substance ID:
24898067
UNSPSC Code:
12352202
MDL number:
MFCD00063527

Key Documents

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InChI key

MHFRGQHAERHWKZ-HHHXNRCGSA-N

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

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

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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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
SLCC8287
SLCC2998
SLBZ1269
SLBR6644V
SLBQ8509V

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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.
Molecular and cellular biochemistry, 398(1-2), 73-81 (2014-09-10)
In anuran amphibians, larval red blood cells (RBCs) are replaced by adult-type RBCs during metamorphosis. We previously showed that tumor necrosis factor-related apoptosis-inducing ligand 1 (TRAIL1) induces apoptosis in larval-, but not adult-type RBCs in Xenopus laevis. We also found
Vítezslav Bryja et al.
Journal of cell science, 120(Pt 4), 586-595 (2007-01-25)
Previously, we have shown that Wnt-5a strongly regulates dopaminergic neuron differentiation by inducing phosphorylation of Dishevelled (Dvl). Here, we identify additional components of the Wnt-5a-Dvl pathway in dopaminergic cells. Using in vitro gain-of-function and loss-of-function approaches, we reveal that casein
M R Pabbidi et al.
PloS one, 11(12), e0168505-e0168505 (2016-12-16)
We previously reported in atrial myocytes that inhibition of cAMP-dependent protein kinase (PKA) by laminin (LMN)-integrin signaling activates β2-adrenergic receptor (β2-AR) stimulation of cytosolic phospholipase A2 (cPLA2). The present study sought to determine the signaling mechanisms by which inhibition of
Cristián Ibarra et al.
Molecular oncology, 13(2), 202-211 (2018-10-26)
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