Triphenylethylene

Triphenylethylene

Identifiers
IUPAC name 1,2-Diphenylethenylbenzene
CAS Number	58-72-0
PubChem CID	6025
ChemSpider	5803
Chemical and physical data
Formula	C20H16
Molar mass	256.34104 g/mol
3D model (Jmol)	Interactive image
SMILES C1=CC=C(C=C1)C=C(C2=CC=CC=C2)C3=CC=CC=C3
InChI 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 Key:MKYQPGPNVYRMHI-UHFFFAOYSA-N

Triphenylethylene (TPE) is a simple aromatic hydrocarbon that possesses weak estrogenic activity. Its estrogenic effects were discovered in 1937. TPE was derived from structural modification of the more potent estrogen diethylstilbestrol, which is a member of the stilbestrol group of non-steroidal estrogens.

TPE is the parent compound of a group of non-steroidal estrogen receptor ligands. It includes the estrogens chlorotrianisene, estrobin (DBE), 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.