66422-18-2

Usage

Molecular structure

A phenylethylene molecule with two hydroxyphenyl groups attached to the carbon atoms at positions 1 and 2

Usage

Widely used in the production of polycarbonate plastics and epoxy resins

Applications

Found in food containers, water bottles, dental sealants, and thermal paper receipts

Health concerns

Potential health effects due to leaching from products

Presence in humans

Detected in human urine, blood, and breast milk

Health risks

Linked to hormonal imbalances, reproductive issues, and an increased risk of certain cancers

Current interest

Growing interest in finding alternative compounds to replace bisphenol A in products due to its potential health risks

Upstream product

• 1023-17-2 4-methoxyphenyl benzyl ketone 
• 103-80-0 phenylacetyl chloride 
• 100-66-3 methoxybenzene 
• 31067-04-6 1,1-bis(4-methoxyphenyl)-2-phenylethanol 
• 10035-10-6 hydrogen bromide 
• 64-19-7 acetic acid 
• 7664-93-9 sulfuric acid 
• 611-99-4 4,4'-Dihydroxybenzophenone 
• 874005-02-4 1,1-bis-(4-isopropoxy-phenyl)-2-phenyl-ethene 
• 26642-57-9 1,1-bis(4-methoxyphenyl)-2-phenylethene 

Downstream Products

• 6192-24-1 1,1-bis-(4-acetoxy-phenyl)-2-bromo-2-phenyl-ethene 
• 106692-20-0 1-bromo-2,2-bis-(4-hydroxy-phenyl)-1-phenyl-ethene 

Relevant academic research and scientific papers

Investigations on estrogen receptor binding. The estrogenic, antiestrogenic, and cytotoxic properties of C2-alkyl-substituted 1,1-bis(4-hydroxyphenyl)-2-phenylethenes

C2-Alkyl-substituted 1,1-bis(4-hydroxyphenyl)-2-phenylethenes were synthesized and assayed for estrogen receptor binding in a competition experiment with radiolabeled estradiol ([3H]-E2) using calf uterine cytosol. The relative binding affinity decreased with the length of the side chain R = H (3a: 35.2%) > Me (3b: 32.1%) 2CF3 (3d: 5.95%) > n-Pr (3e: 2.09%) > Bu (3f: 0.62%). Agonistic and antagonistic effects were evaluated in the luciferase assay with MCF-7-2a cells stably transfected with the plasmid EREwtcluc. All compounds showed high antiestrogenic activity without significant agonistic potency. The comparison of the IC50 values for the inhibition of E2 (1 nM) documented the dependence of the antagonistic effects on the kind of the side chain: 3a (IC50 = 150 nM), 3b (IC50 = 30 nM), and 3f (IC50 = 500 nM) were weak antagonists, while 3c (IC50 = 15 nM), 3d (IC50 = 9 nM), and 3e (IC50 = 50 nM) were full antiestrogens and antagonized the effect of E2 completely. The most active compound 3d possessed the same antagonistic potency as 4-hydroxytamoxifen (40HT: IC50= 7 nM) without bearing a basic side chain. 3d as well as all other 1,1-bis(4-hydroxyphenyl)-2-phenylalkenes were not able to influence the proliferation of hormone dependent MCF-7 cells despite the antagonistic mode of action. In this assay tamoxifen (TAM) and 40HT reduced the cell growth concentration dependent up to T/Ccorr = 15% and 25%, respectively.