91221-46-4

Basic information

• Product Name: 1,1-bis(4-hydroxyphenyl)-2-phenylbut-1-ene
• Synonyms: 1,1-bis(4-hydroxyphenyl)-2-phenylbut-1-ene;1,1-Bis(4-hydroxyphenyl)-2-phenyl-1-butene;4,4'-(2-Phenyl-1-butenylidene)bisphenol
• CAS NO: 91221-46-4
• Molecular Formula: C₂₂H₂₀O₂
• Molecular Weight: 316.393
• Product Categories: Aromatics;Miscellaneous Reagents
• Mol File: 91221-46-4.mol
• Article Data: 25

Chemical Properties

• Melting Point: 202°C(lit.)
• Boiling Point: 457.7°Cat760mmHg
• Flash Point: 207.2°C
• Appearance: /
• Density: 1.161g/cm³
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Methanol
• CAS DataBase Reference: 1,1-bis(4-hydroxyphenyl)-2-phenylbut-1-ene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-bis(4-hydroxyphenyl)-2-phenylbut-1-ene(91221-46-4)
• EPA Substance Registry System: 1,1-bis(4-hydroxyphenyl)-2-phenylbut-1-ene(91221-46-4)

Safety Data

• Hazardous Substances Data: 91221-46-4(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Upstream product

• 850256-19-8 E/Z-1-(4-hydroxyphenyl)-1-(4-methoxyphenyl)-2-phenylbutene 
• 32770-66-4 1-(1-phenylpropylidene)hydrazine 
• 93-55-0 1-phenyl-propan-1-one 
• 71597-85-8 (p-hydroxyphenyl)boronic acid 
• 144108-80-5 1-(1,1-dibromobut-1-en-2-yl)benzene 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 82413-27-2 1-(3-methoxyphenyl)-2-phenyl-butan-1-one 
• 100-66-3 methoxybenzene 
• 1023-17-2 4-methoxyphenyl benzyl ketone 
• 103-80-0 phenylacetyl chloride 
• 78423-10-6 1-(4-methoxyphenyl)-2-phenylbutan-1-one 
• 40595-34-4 (E)-trimethyl(3-phenylallyl)silane 
• 95592-67-9 4-pivaloyloxybenzaldehyde 
• 886463-36-1 4-(4-methoxyphenyl)-4-[4-(pivaloyloxy)phenyl]-3-phenylbut-1-ene 

Downstream Products

• 82333-70-8 1,1-Bis(4'-acetoxyphenyl)-2-phenyl-but-1-en 
• 1388825-74-8 (S)-tert-butyl 2-((4-(1-(4-hydroxyphenyl)-2-phenylbut-1-enyl)phenoxy)methyl)pyrrolidine-1-carboxylate 
• 1020853-03-5 2-phenyl-1,1-bis{4-[2-(azepan-1-yl)ethoxy]phenyl}but-1-ene 
• 1217237-98-3 4-(1-(4-(2-aminoethoxy)phenyl)-2-phenylbut-1-en-1-yl)phenol 
• 68392-35-8 4-hydroxytamoxifen 
• 147323-02-2 E/Z-1-[4-(2-bromoethoxy)phenyl]-1-(4-hydroxyphenyl)-2-phenylbutene 
• 141777-00-6 (E,Z)-4-<1-(p-hydroxyphenyl)-2-phenyl-1-butenyl>phenoxyacetic acid 
• 1440533-05-0 (E)-2-(4-(1-(4-hydroxyphenyl)-2-phenylbut-1-enyl)phenoxy)acetamide 
• 1440533-04-9 (Z)-2-(4-(1-(4-hydroxyphenyl)-2-phenylbut-1-enyl)phenoxy)acetamide 
• 1370699-82-3 (4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenylbut-1-en-1-yl)phenyl)boronic acid 
• 1371574-63-8 potassium [4-(1-{4-[2-(dimethylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl)phenyl]trifluoroboranuide 
• 1370699-81-2 N,N-dimethyl-2-(4-(2-phenyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)but-1-en-1-yl)phenoxy)ethanamine 
• 1370699-80-1 (E,Z)-4-(1-{4-[2-(dimethylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl)phenyl trifluoromethanesulfonate 
• 1290637-40-9 1,1-bis(4-palmitoyloxyphenyl)-2-phenylbut-1-ene 

Relevant articles and documents

Modification of the estrogenic properties of diphenols by the incorporation of ferrocene. Generation of antiproliferative effects in vitro

We report here the synthesis and the strong and unexpected antiproliferative effect of the organometallic diphenolic compound 1,1-bis(4′-hydroxyphenyl)-2-ferrocenyl-but-1-ene (4) on both hormone-dependent (MCF7) and -independent (MDA-MB231) breast cancer cells (IC50 = 0.7 and 0.6 μM). Surprisingly, 6 [1,2-bis(4′- hydroxyphenyl)-2-ferrocenyl-but-1-ene], the regioisomer of 4, shows only a modest effect on these cell lines. This pertinent organometallic modification seems to trigger an intracellular oxidation of the structurally favorable compound 4, leading to the generation of a potent cytotoxic compound.

Synthesis of Tamoxifen-Artemisinin and Estrogen-Artemisinin Hybrids Highly Potent Against Breast and Prostate Cancer

In the search for new and effective treatments of breast and prostate cancer, a series of hybrid compounds based on tamoxifen, estrogens, and artemisinin were successfully synthesized and analyzed for their in vitro activities against human prostate (PC-3) and breast cancer (MCF-7) cell lines. Most of the hybrid compounds exhibit a strong anticancer activity against both cancer cell lines – for example, EC50 (PC-3) down to 1.07 μM, and EC50 (MCF-7) down to 2.08 μM – thus showing higher activities than their parent compounds 4-hydroxytamoxifen (afimoxifene, 7; EC50=75.1 (PC-3) and 19.3 μM (MCF-7)), dihydroartemisinin (2; EC50=263.6 (PC-3) and 49.3 μM (MCF-7)), and artesunic acid (3; EC50=195.1 (PC-3) and 32.0 μM (MCF-7)). The most potent compounds were the estrogen-artemisinin hybrids 27 and 28 (EC50=1.18 and 1.07 μM, respectively) against prostate cancer, and hybrid 23 (EC50=2.08 μM) against breast cancer. These findings demonstrate the high potential of hybridization of artemisinin and estrogens to further improve their anticancer activities and to produce synergistic effects between linked pharmacophores.

NOVEL COMPOUNDS HAVING ESTROGEN RECEPTOR ALPHA DEGRADATION ACTIVITY AND USES THEREOF

The present disclosure relates to novel compounds having estrogen receptor alpha degradation activity, pharmaceutical compositions containing such compounds, and their use in prevention and treatment of cancer and related diseases and conditions.

New approach based on immunochemical techniques for monitoring of selective estrogen receptor modulators (SERMs) in human urine

Antiestrogenic compounds such as tamoxifen, toremifen and chlomifen are used illegally by athletes to minimize physical impacts such as gynecomastia resulting from the secondary effects of anabolic androgenic steroids, used to increase athletic efficiency unlawfully. The use of these compounds is banned by the World Anti-Doping Agency (WADA) and controls are made through analytical methodologies such as HPLC–MS/MS, which do not fulfil the sample throughput requirements. Moreover, compounds such as tamoxifen are also used to treat hormone receptor-positive breast cancer (ER +).Therapeutic drug monitoring (TDM) of tamoxifen may also be clinically useful for guiding treatment decisions. An accurate determination of these drugs requires a solid phase extraction of patient serum followed by HPLC–MS/MS. In the context of an unmet need of high-throughput screening (HTS) and quantitative methods for antiestrogenic substances we have approached the development of antibodies and an immunochemical assay for the determination of these antiestrogenic compounds. The strategy applied has taken into consideration that these drugs are metabolized and excreted in urine as the corresponding 4-hydroxylated compounds. A microplate-based ELISA procedure has been developed for the analysis of these metabolites in urine with a LOD of 0.15, 0.16 and 0.63 μg/L for 4OH-tamoxifen, 4OH-toremifen and 4OH-clomifen, respectively, much lower than the MRPL established by WADA (20 μg/L).