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T82805

Sigma-Aldrich

Triphenylethylene

99%

Synonym(s):

1,1,2-Triphenylethene, 1,1,2-Triphenylethylene, 1,1′,1′′-(1-Ethenyl-2-ylidene)tris[benzene], 1,2-Diphenylethenylbenzene, Benzilidenediphenylmethane, Ethene-1,1,2-triyltribenzene

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About This Item

Linear Formula:
C6H5CH=C(C6H5)2
CAS Number:
58-72-0
Molecular Weight:
256.34
Beilstein:
1867462
EC Number:
200-395-1
MDL number:
MFCD00004765
UNSPSC Code:
12352100
PubChem Substance ID:
24900519
NACRES:
NA.22

Assay

99%

mp

69-71 °C (lit.)

SMILES string

c1ccc(cc1)\C=C(/c2ccccc2)c3ccccc3

InChI

1S/C20H16/c1-4-10-17(11-5-1)16-20(18-12-6-2-7-13-18)19-14-8-3-9-15-19/h1-16H

InChI key

MKYQPGPNVYRMHI-UHFFFAOYSA-N

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Application

Triphenylethylene is an aromatic hydrocarbon, which can be used as a starting material to prepare 2,2,3-triphenyloxirane by asymmetric epoxidation reaction using fluorous chiral manganese complex as a catalyst. It is also used to prepare dihydro-4,5,5-triphenyl-2(3H)-furanone by reacting with acetic anhydride in the presence of MnO2 and NaOAc.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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H Wiseman et al.
Chemico-biological interactions, 79(2), 229-243 (1991-01-01)
The azole antifungal drug ketoconazole was found to inhibit Fe(III)-ascorbate dependent lipid peroxidation using either rat liver microsomes or ox-brain phospholipid liposomes as the substrate. It also inhibited microsomal peroxidation induced by the Fe(III)-ADP/NADPH system. The related azoles, miconazole and
Speculation on the mechanism of action of triphenylethylene antioestrogens.
C D van den Koedijk et al.
Biochemical pharmacology, 47(11), 1927-1937 (1994-06-01)
Yuliya Dobrydneva et al.
Journal of cardiovascular pharmacology, 50(4), 380-390 (2007-12-01)
The anti-estrogenic drug tamoxifen, which is used therapeutically for treatment and prevention of breast cancer, can lead to the development of thrombosis. We found that tamoxifen rapidly increased intracellular free calcium [Ca2+]i in human platelets from both male and female
S J Gatley et al.
International journal of radiation applications and instrumentation. Part B, Nuclear medicine and biology, 18(7), 769-775 (1991-01-01)
A triphenylethylene compound [1,1-bis(4-hydroxyphenyl)-2-iodo-2-phenylethylene; IBHPE] has been labeled by halodestannylation with 123I at a specific radioactivity of 13,200 Ci/mmol (by in vitro receptor assay) after HPLC purification. The corresponding 80mBr-labeled compound (BrBHPE), which has a 3-fold higher affinity for the
E Bignon et al.
FEBS letters, 271(1-2), 54-58 (1990-10-01)
The activation of type I (gamma), II (beta) and III (alpha) protein kinase C (PKC) subspecies by phosphatidylserine (PS) and diacylglycerol (DAG) is inhibited by micromolar concentrations of triphenylacrylonitrile (TPE) antiestrogens. TPE A (with p-hydroxy and p-diethylaminoethoxy groups on the
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