227947-06-0

Basic information

• Product Name: BISPHENOL A-(3-CHLORO-2-HYDROXYPROPYL)-&
• Synonyms: BISPHENOL A-(3-CHLORO-2-HYDROXYPROPYL)-&;BISPHENOL A 3-CHLORO-2-HYDROXYPROPYL DIH;2-[4-(3-chloro-2-hydroxypropyloxy)phenyl]-2-[4-(2,3-dihydroxypropyloxy)phenyl]propane;BADGE-HCl-H2O, 2-[4-(3-Chloro-2-hydroxypropyloxy)phenyl]-2-[4-(2,3-dihydroxypropyloxy)phenyl]propane;Bisphenol A (3-chloro-2-hydroxypropyl) (2,3-dihydroxypropyl) ether,2-[4-(3-Chloro-2-hydroxypropyloxy)phenyl]-2-[4-(2,3-dihydroxypropyloxy)phenyl]propane, BADGE-HCl-H2O;BADGE-HCl-H2O;EPI-001;3-[4-[1-[4-(3-Chloro-2-hydroxypropoxy)phenyl]-1-methylethyl]phenoxy]-1,2-propanediol
• CAS NO: 227947-06-0
• Molecular Formula: C₂₁H₂₇ClO₅
• Molecular Weight: 394.892
• EINECS: 200-258-5
• Mol File: 227947-06-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: 67 °C
• Boiling Point: 601 °C at 760 mmHg
• Flash Point: 317.2 °C
• Appearance: white to beige/
• Density: 1.228 g/cm³
• Vapor Pressure: 2.72E-15mmHg at 25°C
• Refractive Index: 1.571
• Storage Temp.: 2-8°C
• Solubility: DMSO: soluble15mg/mL, clear
• PKA: 13.13±0.20(Predicted)
• CAS DataBase Reference: BISPHENOL A-(3-CHLORO-2-HYDROXYPROPYL)-&(CAS DataBase Reference)
• NIST Chemistry Reference: BISPHENOL A-(3-CHLORO-2-HYDROXYPROPYL)-&(227947-06-0)
• EPA Substance Registry System: BISPHENOL A-(3-CHLORO-2-HYDROXYPROPYL)-&(227947-06-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 227947-06-0(Hazardous Substances Data)

Usage

Description

BISPHENOL A-(3-CHLORO-2-HYDROXYPROPYL)-& is a chemical compound with a specific molecular structure that features a bisphenol A core and a 3-chloro-2-hydroxypropyl functional group. BISPHENOL A-(3-CHLORO-2-HYDROXYPROPYL)-& is known for its unique properties and potential applications in various industries.

Uses

Used in Pharmaceutical Industry:
BISPHENOL A-(3-CHLORO-2-HYDROXYPROPYL)-& is used as a selective peroxisome proliferator-activated receptor-gamma modulator for inhibiting androgen receptor expression and activity in prostate cancer. It serves as a novel androgen receptor antagonist with the potential for treating prostate cancer.
Used in Chemical Synthesis:
BISPHENOL A-(3-CHLORO-2-HYDROXYPROPYL)-& can be utilized as a key intermediate in the synthesis of various chemical products, such as polymers, resins, and other specialty chemicals. Its unique functional groups allow for further chemical modifications and the development of new materials with tailored properties.
Used in Research and Development:
Due to its specific molecular structure, BISPHENOL A-(3-CHLORO-2-HYDROXYPROPYL)-& may be employed in research and development for studying the effects of structural modifications on the properties and applications of bisphenol A-based compounds. This can lead to the discovery of new compounds with improved characteristics and broader applications.

Biological Activity

epi-001 is a small-molecule inhibitor of androgen receptor n-terminal domain. epi-001 could target the amino terminal domain of the ar and inhibit the protein-protein interactions which are necessary for ar transcriptional activity. the androgen receptor (ar) is involved in mediating the actions of male sex steroids. amplification and over-expression of androgen receptor gene may result in hormone-refractory prostate cancer [1].

in vitro

epi-001 inhibited the ligand-dependent argal4 transcriptional activity in lncap cells and the ligand-independent argal4 transcriptional activity in the crpc c4-2 cell line. in a panel of cell lines, epi-001 treatment decreased the mrna expression level of ar protein after 8 and 16 h treatment, such as androgen sensitive pca, crpc, lncap, c4-2, and lapc4 cell line. epi-001 dose-dependently inhibited the pca/crpc cell growth [2].

in vivo

intravenous injection of epi-001 significantly reduced the weight of benign prostates and blocked the growth of prostate cancer xenograft from noncastrated mature mice. epi-001 caused tumor regression of crpc. in male mice bearing lncap xenografts, after treated with epi- 001 by i.v. injection for 2 weeks, the tumor size was less than half of the control group [3].

references

andersen r j, mawji n r, wang j, et al. regression of castrate-recurrent prostate cancer by a small-molecule inhibitor of the amino-terminus domain of the androgen receptor[j]. cancer cell, 2010, 17(6): 535-546.brand l j, olson m e, ravindranathan p, et al. epi-001 is a selective peroxisome proliferator-activated receptor-gamma modulator with inhibitory effects on androgen receptor expression and activity in prostate cancer[j]. oncotarget, 2015, 6(6): 3811.sadar m d. small molecule inhibitors targeting the “achilles' heel” of androgen receptor activity[j]. cancer research, 2011, 71(4): 1208-1213.

InChI:InChI=1/C21H27ClO5/c1-21(2,15-3-7-19(8-4-15)26-13-17(24)11-22)16-5-9-20(10-6-16)27-14-18(25)12-23/h3-10,17-18,23-25H,11-14H2,1-2H3

Upstream product

• 4809-35-2 1-chloro-3-[4-[2-[4-(3-chloro-2-hydroxypropoxy)phenyl] propan-2-yl]phenoxy]propan-2-ol 
• 13634-08-7 C₁₈H₂₂O₄ 
• 5581-32-8 3-[4-[1-[4-(2,3-dihydroxypropoxy)phenyl]-1-methylethyl]phenoxy]propane-1,2-diol 

Downstream Products

• 1203490-40-7 C₄₂H₆₀ClN₃O₁₄ 

Relevant articles and documents

Process for manufacturing an alpha-dihydroxy derivative and epoxy resins prepared therefrom

A process for manufacturing an α-dihydroxy derivative from an aryl allyl ether wherein such α-dihydroxy derivative can be used to prepare an α-halohydrin intermediate and an epoxy resin prepared therefrom including epoxidizing an α-halohydrin intermediate produced from a halide substitution of an α-dihydroxy derivative which has been obtained by a dihydroxylation reaction of an aryl allyl ether in the presence of an oxidant or in the presence of an oxidant and a catalyst.