74385-27-6

Usage

Molecular structure

A central carbon atom bonded to two methyl groups (CH3) and two phenol groups (C6H4OH), with the phenol groups connected to the central carbon through an ethyl bridge (C2H4)

Physical state

Solid at room temperature

Uses

Production of epoxy resins and polycarbonate plastics

Similarity

Closely related to bisphenol-A (BPA), with an additional methyl group on each carbon atom

Advantage

Often used as a replacement for BPA due to its lower estrogenic activity

Health concerns

Potential endocrine-disrupting properties, similar to BPA

Research status

Ongoing research on safety and potential health effects

Regulatory status

Regulations regarding its use in consumer products vary by region

Upstream product

• 32445-98-0 2,3-bis(4-methoxyphenyl)-2,3-dimethylbutane 
• 7428-99-1 2-(4-methoxyphenyl)propan-2-ol 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 121-98-2 methyl 4-methoxybenzoate 

Relevant academic research and scientific papers

Diradical Rearrangements: An Unusual 1,2-Shift in a Photochemically Generated 1,3-Diradical. Mechanistic and Exploratory Organic Photochemistry

The triplet photochemistry of 2,5-dianisyl-2,5-dimethyl-hex-3-ene was explored in a study of the behavior of diradical species occuring in the di-?-methane rearrangement.It was observed that the penultimate species, the 1,3-diradical, closes more rapidly

Ring-substituted 1,1,2,2-tetraalkylated 1,2-bis(hydroxyphenyl)ethanes. 4. Synthesis, estrogen receptor binding affinity, and evaluation of antiestrogenic and mammary tumor inhibiting activity of symmetrically disubstituted 1,1,2,2-tetramethyl-1,2-bis(hydroxyphenyl)ethanes

The syntheses of symmetrically 2,2'-disubstituted derivatives of 1,1,2,2-tetramethyl-1,2bis(4-hydroxyphenyl)ethane (1) are and of 5,5'-, and 6,6'-disubstituted derivatives of 1,1,2,2-tetramethyl-1,2-bis(3-hydroxyphenyl)ethane (6) are described (1 and 6 are strong antiestrogens with mammary tumor inhibiting activity exhibiting only slight estrogenic properties): (2,2'-substituents) F (2), Cl (3), OCH3 (4), CH3 (5); (5,5'-substituents) Cl (7); (6,6'-substituents) F (8), Cl (9), OCH3 (10), CH3 (11). The synthesis of 1-11 was accomplished by reductive coupling of the corresponding 2-phenyl-2-propanols with TiCl3 and LiAlH4. The binding affinity of the compounds to the calf uterine estrogen receptor was measured relative to that of [3H]estradiol by a competitive binding assay. With the exception of 7 and 10 all other compounds showed relative binding affinity (RBA) values between 0.5 and 6.4% that of estradiol, 2 (RBA value 6.4), and 8 and 9 (4.0 and 3.5), exceeding those of the corresponding unsubstituted 1 and 6 (3.6 and 3.0). Compounds exhibiting RBA values of >2.5% were evaluated in the mouse uterine weight test. The substituted derivatives showed an increase in uterotrophic and a decrease in antiuterotrophic activity compared to 1 and 6. Compound 2 showed a strong, dose-dependent inhibition on the DMBA-induced hormone-dependent mammary tumor of the SD-rat, exceeding that of the parent compound 1. At a dose of 5 mg/kg per day, 2 reduced total tumor area by 47% and caused a complete remission in 74% of the tumors.

Antiestrogens. Synthesis and Evaluation of Mammary Tumor Inhibiting Activity of 1,1,2,2-Tetraalkyl-1,2-diphenylethanes

Among the newly synthesized 1,1,2,2-tetraalkyl-1,2-diphenylethanes, 1,1,2,2-tetramethyl-1,2-bis(4'-hydroxyphenyl)ethane (23) and 1,1,2,2-tetramethyl-1,2-bis(3'-hydroxyphenyl)ethane (26) were the most active compounds regarding estradiol receptor affinity, exhibiting Ka values of 0.73*108 and 0.67*108 M-1, respectively.In vivo, 23 and 26 showed only very small uterotrophic activity in the mouse.They strongly inhibited (73percent) the estrone-stimulated mouse uterine growth.Tested on the 9,10-dimethyl-1,2-benzanthracene induced hormone-dependent mammary adenocarcinoma of the Sprague-Dawley rat, compounds 23 and 26 exhibited a dose-dependent inhibition of the tumor growth, having a strong effect at a dose of 20 (mg/kg)/day (compound 23).