1428-67-7

Basic information

• Product Name: 2,3-BIS(4-HYDROXYPHENYL)-PROPIONITRILE
• Synonyms: 2,3-BIS(4-HYDROXYPHENYL)-PROPIONITRILE;DPN;2,3-bis(p-hydroxyphenyl)propionitrile;propionitrile,2,3-bis(p-hydroxyphenyl);2,3-Bis(4-hydroxyphenyl)propanenitrile;2,3-Bis(4-hydroxyphenyl)propiononitrile;Diarylpropionitrile;SC-4473
• CAS NO: 1428-67-7
• Molecular Formula: C₁₅H₁₃NO₂
• Molecular Weight: 239.27
• Product Categories: Miscellaneous;Intracellular receptor;Nuclear Receptors;Diarylpropionitrile
• Mol File: 1428-67-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 200.0 to 204.0 °C
• Boiling Point: 449.4 °C at 760 mmHg
• Flash Point: 225.6 °C
• Appearance: white to beige/
• Density: 1.256 g/cm³
• Vapor Pressure: 1.08E-08mmHg at 25°C
• Refractive Index: 1.639
• Storage Temp.: Desiccate at -20°C
• Solubility: DMSO: soluble10mg/mL, clear
• Water Solubility: Soluble in 1eq. NaOH (30 mM), ethanol (100 mM), DMSO (100 mM), DMF (~30 mg/ml), and water (0.5 mg/ml at 25°C).
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.
• CAS DataBase Reference: 2,3-BIS(4-HYDROXYPHENYL)-PROPIONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-BIS(4-HYDROXYPHENYL)-PROPIONITRILE(1428-67-7)
• EPA Substance Registry System: 2,3-BIS(4-HYDROXYPHENYL)-PROPIONITRILE(1428-67-7)

Safety Data

• Hazard Codes: Xi,N
• Statements: 36-50
• Safety Statements: 26-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• RTECS: UG0900000
• HazardClass: 9
• Hazardous Substances Data: 1428-67-7(Hazardous Substances Data)

Usage

Description

DPN (1428-67-7) is a potent estrogen ERβ receptor agonist. Displays a 70-fold selectivity over ERα, EC50 = 0.85 and 66 nM, respectively.1 Regulates expression of GluR1, 2 and 3 in rat hippocampus.2 Ameliorates portal hypertension in a carbon tetrachloride-induced liver cirrhosis rat model.3 Stimulates proliferation of androgen-independent prostate cancer cell line PC-3 via a novel pathway involving ERβ-mediated activation of β-catenin.4 A useful tool for elucidating the biological function of ERβ.5

Uses

2,3-Bis(4-hydroxyphenyl)propionitrile is an estrogen receptor β and α specific with pro- and anti-nociceptive actions in mice.

Definition

ChEBI: A nitrile that is acetonitrile in which one of the hydrogens is replaced by a 4-hydroxyphenyl group while a second hydrogen is replaced by a 4-hydroxybenzyl group. It is a specific agonist for estrogen receptor beta (ERbeta).

Biological Activity

Highly potent estrogen ER β receptor agonist with a 70-fold selectivity over ER α (EC 50 values are 0.85 and 66 nM respectively). Relaxes mesenteric arteries in vitro .

Biochem/physiol Actions

2,3-Bis(4-hydroxyphenyl)-propionitrile (Diarylprepionitrile, DPN) is an ERβ-selective agonist; IC50 = 15nM. DPN protects WT and ARKO mice and significantly decreases IL-1β following LPS treatment in young adult-derived microglia. PPT (Cat. No.H6036, ERa agonist) enhances cell proliferation, while DPN inhibits it. PPT increases Bcl-2 expression, while DPN decreases it. DPN also elevates Bax expression. DPN induces a dose-dependent increase on vitellogenin synthesis. PPT and DPN are effective in dynamically, but differentially regulating intracellular calcium signaling in hippocampal neurons. DPN is more efficacious than PPT in potentiating a physiological concentration of glutamate-induced intracellular Ca2+ rise in these neurons. DPN prevents the development of prostatic hyperplasia and inflammation in testosterone-treated LuRKO mice.

References

1) Meyers et al. (2001), Estrogen receptor-beta potency-selective ligands: structure-activity relationship studies of diarylpropionitriles and their acetylene and polar analogues; J. Med. Chem., 44 4230 2) Waters et al. (2009), Estrogen receptor alpha and beta specific agonists regulate expression of synaptic proteins in rat hippocampus; Brain Res., 1290 1 3) Zhang et al. (2016), Role of estrogen receptor beta selective agonist in ameliorating portal hypertension in rats with CC14-induced liver cirrhosis; World J. Gastroenterol., 22 4484 4) Lombardi et al. (2016), Estrogen receptor beta (ERβ) mediates expression of β-catenin and proliferation in prostate cancer cell line PC-3; Mol. Cell. Endocrin. 430 12 5) Harrington et al. (2003), Activities of estrogen receptor alpha- and beta-selective ligands at diverse estrogen responsive gene sites mediating transactivation and transrepression; Mol. Cell. Endocrinol., 206 13

InChI:InChI=1/C15H13NO2/c16-10-13(12-3-7-15(18)8-4-12)9-11-1-5-14(17)6-2-11/h1-8,13,17-18H,9H2

Upstream product

• 72035-46-2 2,3-bis(4-methoxyphenyl)propanenitrile 
• 123-11-5 4-methoxy-benzaldehyde 
• 104-47-2 p-methoxybenzylnitrile 
• 6443-74-9 p-methoxy-α-p-methoxyphenylcinnamonitrile 
• 2746-25-0 p-Methoxybenzyl bromide 

Relevant articles and documents

Synthetic method 2,3 - bis (4 - hydroxyphenyl) propionitrile

2 Is disclosed. 3 - Bis (4 - hydroxyphenyl) propionitrile synthesis method relates to the technical field of electrolyte additives. To the scheme, methoxybenzene acetonitrile is dissolved in an organic solvent,5 - 0 °C of sodium hydride is added,5 - 0 °C

Diarylpropionitrile (DPN) enantiomers: Synthesis and evaluation of estrogen receptor β-selective ligands

Two estrogen receptor (ER) subtypes, ERα and ERβ, mediate the actions of estrogens in diverse reproductive and nonreproductive target tissues. ER subtype-selective ligands, which bind to and activate these subtypes differentially, have proved to be useful