2,3-BIS(4-HYDROXYPHENYL)-PROPIONITRILE
- Product Name
- 2,3-BIS(4-HYDROXYPHENYL)-PROPIONITRILE
- CAS No.
- 1428-67-7
- Chemical Name
- 2,3-BIS(4-HYDROXYPHENYL)-PROPIONITRILE
- Synonyms
- DPN;SC-4473;Diarylpropionitrile;2,3-bis(p-hydroxyphenyl)propionitrile;2,3-BIS(4-HYDROXYPHENYL)-PROPIONITRILE;propionitrile,2,3-bis(p-hydroxyphenyl);2,3-Bis(4-hydroxyphenyl)propanenitrile;2,3-Bis(4-hydroxyphenyl)propiononitrile;2,3-Bis(4-hydroxyphenyl)propionitrile >Benzenepropanenitrile, 4-hydroxy-α-(4-hydroxyphenyl)-
- CBNumber
- CB2379797
- Molecular Formula
- C15H13NO2
- Formula Weight
- 239.27
- MOL File
- 1428-67-7.mol
2,3-BIS(4-HYDROXYPHENYL)-PROPIONITRILE Property
- Melting point:
- 200.0 to 204.0 °C
- Boiling point:
- 449.4±35.0 °C(Predicted)
- Density
- 1.256±0.06 g/cm3(Predicted)
- RTECS
- UG0900000
- storage temp.
- -20°C
- solubility
- DMSO: soluble10mg/mL, clear
- pka
- 9.41±0.26(Predicted)
- form
- powder
- color
- white to beige
- 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.
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H319Causes serious eye irritation
H400Very toxic to aquatic life
- Precautionary statements
-
P273Avoid release to the environment.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- H5915
- Product name
- 2,3-Bis(4-hydroxyphenyl)propionitrile
- Purity
- ≥98% (HPLC)
- Packaging
- 5mg
- Price
- $51.6
- Updated
- 2024/03/01
- Product number
- H5915
- Product name
- 2,3-Bis(4-hydroxyphenyl)propionitrile
- Purity
- ≥98% (HPLC)
- Packaging
- 25mg
- Price
- $347
- Updated
- 2024/03/01
- Product number
- B4385
- Product name
- 2,3-Bis(4-hydroxyphenyl)propionitrile
- Purity
- >98.0%(GC)
- Packaging
- 10mg
- Price
- $82
- Updated
- 2024/03/01
- Product number
- B4385
- Product name
- 2,3-Bis(4-hydroxyphenyl)propionitrile
- Purity
- >98.0%(GC)
- Packaging
- 50mg
- Price
- $280
- Updated
- 2024/03/01
- Product number
- 10008842
- Product name
- 2,3-bis (4-Hydroxyphenyl) Propionitrile
- Purity
- ≥98%
- Packaging
- 5mg
- Price
- $39
- Updated
- 2024/03/01
2,3-BIS(4-HYDROXYPHENYL)-PROPIONITRILE Chemical Properties,Usage,Production
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.
storage
-20°C (desiccate)
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
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