Triphenylethylene
Chemical compound
From Wikipedia, the free encyclopedia
Triphenylethylene (TPE) is the organic compound with the formula (C6H5)2C=CH(C6H5). It is a colorless solid.
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| Names | |
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| IUPAC name
1,1',1''-(Ethene-1,1,2-triyl)tribenzene | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.000.359 |
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| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C20H16 | |
| Molar mass | 256.348 g·mol−1 |
| Appearance | white solid |
| Density | 1.163 g/cm3[1] |
| Melting point | 65–67.5 °C (149.0–153.5 °F; 338.1–340.6 K) |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H302, H319, H410 | |
| P264, P264+P265, P270, P273, P280, P301+P317, P305+P351+P338, P330, P337+P317, P391, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis and reactions
The compound is prepared in two steps from benzophenone via the intermediacy of 1,2,2-triphenylethanol.[2] Triphenylethylene reacts with iodine to give 9-phenylphenanthroline.[3] Epoxidation gives the chiral oxirane.[4]
Bioactivity
Triphenylethylene possesses weak estrogenic activity.[5][6] Its estrogenic effects were discovered in 1937.[7] TPE was derived from structural modification of the more potent estrogen diethylstilbestrol, which is a member of the stilbestrol group of nonsteroidal estrogens.[8]
TPE is the parent compound of a group of nonsteroidal estrogen receptor ligands.[5][6][9] It includes the estrogens chlorotrianisene, desmethylchlorotrianisene, estrobin (DBE), M2613, triphenylbromoethylene, triphenylchloroethylene, triphenyliodoethylene, triphenylmethylethylene; the selective estrogen receptor modulators (SERMs) afimoxifene, brilanestrant, broparestrol, clomifene, clomifenoxide, droloxifene, endoxifen, etacstil, fispemifene, idoxifene, miproxifene, miproxifene phosphate, nafoxidine, ospemifene, panomifene, and toremifene. The antiestrogen ethamoxytriphetol (MER-25) is also closely related, but is technically not a derivative of TPE and is instead a triphenylethanol derivative. The tamoxifen metabolite and aromatase inhibitor norendoxifen is also a TPE derivative. In addition to their estrogenic activity, various TPE derivatives like tamoxifen and clomifene have been found to act as protein kinase C inhibitors.[10]
The affinity of triphenylethylene for the rat estrogen receptor is about 0.002% relative to estradiol.[11][12] For comparison, the relative binding affinities of derivatives of triphenylethylene were 1.6% for tamoxifen, 175% for afimoxifene (4-hydroxytamoxifen), 15% for droloxifene, 1.4% for toremifene (4-chlorotamoxifen), 0.72% for clomifene, and 0.72% for nafoxidine.[13][11][12]