CAS 1428-67-7|2,3-bis(4-hydroxyphenyl)propionitrile

Introduction：Basic information about CAS 1428-67-7|2,3-bis(4-hydroxyphenyl)propionitrile, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. 2,3-bis(4-hydroxyphenyl)propionitrile BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Articles14
7. Synonyms

Common Name	2,3-bis(4-hydroxyphenyl)propionitrile
CAS Number	1428-67-7	Molecular Weight	239.269
Density	1.3±0.1 g/cm3	Boiling Point	449.4±35.0 °C at 760 mmHg
Molecular Formula	C₁₅H₁₃NO₂	Melting Point	203°C
MSDS	USA	Flash Point	225.6±25.9 °C
Symbol	GHS07, GHS09	Signal Word	Warning

Names

Name	2,3-bis(4-hydroxyphenyl)propionitrile
Synonym	More Synonyms

2,3-bis(4-hydroxyphenyl)propionitrile BiologicalActivity

Description	Diarylpropionitrile(DPN) is a non-steroidal estrogen receptor β(ER β) selective ligand.IC50 value:Target: ER β ligandin vitro: Pre-treatment with 1-100 nM DPN significantly decreased neuronal cell death by increasing cell viability through a significant attenuation in the reactive oxygen species level, downregulation of pro-apoptotic activated caspase-3 and Bax, and upregulation of anti-apoptotic Bcl-2, thereby mitigating apoptotic morphological alterations. DPN pre-treatment decreased the expression levels of pro-inflammatory cytokines IL-1β and IL-6 through attenuation of Aβ1-42-induced phosphorylation of mitogen-activated protein kinases JNK and p38. In addition, DPN enhanced ERK1/2 and Akt phosphorylation depressed by Aβ1-42 [1]. ERβ was expressed in RAW264.7 cells, and DPN statistically significantly decreased LPS-induced RANTES production in RAW264.7 cells. Small interfering RNA targeting the ERβ gene inhibited the effect of DPN on RANTES production. In addition, DPN inhibited nuclear translocation and phosphorylation of p65 by inhibiting IκB degradation and thus prohibited the activation of nuclear factor κB (NF-κB) [3].in vivo: DPN treatment during EAE did not attenuate demyelination, only partially improved axon conduction, and did not activate the phosphatidylinositol 3-kinase/serine-threonine-specific protein kinase/mammalian target of rapamycin signaling pathway in ERβ CKO mice [2].
Related Catalog	Signaling Pathways >>Others >>Estrogen Receptor/ERRResearch Areas >>Neurological Disease
References	[1]. Suwanna N, et al. Neuroprotective effects of diarylpropionitrile against β-amyloid peptide-induced neurotoxicity in rat cultured cortical neurons. Neurosci Lett. 2014 Aug 22;578:44-9. [2]. Khalaj AJ, et al. Estrogen receptor (ER) β expression in oligodendrocytes is required for attenuation of clinical disease by an ERβ ligand. Proc Natl Acad Sci U S A. 2013 Nov 19;110(47):19125-30. [3]. Huang SY, et al. Estrogen receptor β agonist diarylpropionitrile inhibits lipopolysaccharide-induced regulated on activation normal T cell expressed and secreted (RANTES) production in macrophages by repressing nuclear factor κB activation. Fertil Steril.

Description

Diarylpropionitrile(DPN) is a non-steroidal estrogen receptor β(ER β) selective ligand.IC50 value:Target: ER β ligandin vitro: Pre-treatment with 1-100 nM DPN significantly decreased neuronal cell death by increasing cell viability through a significant attenuation in the reactive oxygen species level, downregulation of pro-apoptotic activated caspase-3 and Bax, and upregulation of anti-apoptotic Bcl-2, thereby mitigating apoptotic morphological alterations. DPN pre-treatment decreased the expression levels of pro-inflammatory cytokines IL-1β and IL-6 through attenuation of Aβ1-42-induced phosphorylation of mitogen-activated protein kinases JNK and p38. In addition, DPN enhanced ERK1/2 and Akt phosphorylation depressed by Aβ1-42 [1]. ERβ was expressed in RAW264.7 cells, and DPN statistically significantly decreased LPS-induced RANTES production in RAW264.7 cells. Small interfering RNA targeting the ERβ gene inhibited the effect of DPN on RANTES production. In addition, DPN inhibited nuclear translocation and phosphorylation of p65 by inhibiting IκB degradation and thus prohibited the activation of nuclear factor κB (NF-κB) [3].in vivo: DPN treatment during EAE did not attenuate demyelination, only partially improved axon conduction, and did not activate the phosphatidylinositol 3-kinase/serine-threonine-specific protein kinase/mammalian target of rapamycin signaling pathway in ERβ CKO mice [2].

Related Catalog

Signaling Pathways >>Others >>Estrogen Receptor/ERRResearch Areas >>Neurological Disease

References

[1]. Suwanna N, et al. Neuroprotective effects of diarylpropionitrile against β-amyloid peptide-induced neurotoxicity in rat cultured cortical neurons. Neurosci Lett. 2014 Aug 22;578:44-9.

[2]. Khalaj AJ, et al. Estrogen receptor (ER) β expression in oligodendrocytes is required for attenuation of clinical disease by an ERβ ligand. Proc Natl Acad Sci U S A. 2013 Nov 19;110(47):19125-30.

[3]. Huang SY, et al. Estrogen receptor β agonist diarylpropionitrile inhibits lipopolysaccharide-induced regulated on activation normal T cell expressed and secreted (RANTES) production in macrophages by repressing nuclear factor κB activation. Fertil Steril.

Chemical & Physical Properties

Density	1.3±0.1 g/cm3
Boiling Point	449.4±35.0 °C at 760 mmHg
Melting Point	203°C
Molecular Formula	C₁₅H₁₃NO₂
Molecular Weight	239.269
Flash Point	225.6±25.9 °C
Exact Mass	239.094635
PSA	64.25000
LogP	2.06
Vapour Pressure	0.0±1.1 mmHg at 25°C
Index of Refraction	1.640
InChIKey	GHZHWDWADLAOIQ-UHFFFAOYSA-N
SMILES	N#CC(Cc1ccc(O)cc1)c1ccc(O)cc1
Storage condition	-20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UG0900000

CHEMICAL NAME :: Propionitrile, 2,3-bis(p-hydroxyphenyl)

CAS REGISTRY NUMBER :: 1428-67-7

BEILSTEIN REFERENCE NO. :: 3337109

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C15-H13-N-O2

MOLECULAR WEIGHT :: 239.29

WISWESSER LINE NOTATION :: QR DYCN&1R DQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1500 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - muscle weakness Behavioral - ataxia

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 112,176,1954

Safety Information

Symbol	GHS07, GHS09
Signal Word	Warning
Hazard Statements	H319-H400
Precautionary Statements	P273-P305 + P351 + P338
Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Gloves
RIDADR	UN 3077 9 / PGIII

Articles14

A precisely substituted benzopyran targets androgen refractory prostate cancer cells through selective modulation of estrogen receptors.

Toxicol. Appl. Pharmacol. 283(3) , 187-97, (2015)

Dietary consumption of phytoestrogens like genistein has been linked with lower incidence of prostate cancer. The estradiol-like benzopyran core of genistein confers estrogen receptor-β (ER-β) selecti...

Classical and membrane-initiated estrogen signaling in an in vitro model of anterior hypothalamic kisspeptin neurons.

Endocrinology 156 , 2162-73, (2015)

The neuropeptide kisspeptin is essential for sexual maturation and reproductive function. In particular, kisspeptin-expressing neurons in the anterior rostral periventricular area of the third ventric...

Methyltransferase-like 17 physically and functionally interacts with estrogen receptors.

IUBMB Life 67 , 861-8, (2016)

Estrogen exerts its physiological and pathological functions through two estrogen receptors (ERs), ERα and ERβ, which act as transcription factors. Coregulators, including coactivators and corepressor...

Synonyms

2,3-bis(4-hydroxyphenyl)propionitrile

DPN Diarylpropionitrile SC-4473

2,3-Bis(4-hydroxyphenyl)propanenitrile

Benzenepropanenitrile, 4-hydroxy-α-(4-hydroxyphenyl)-

DPN

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