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H5915

Sigma-Aldrich

2,3-Bis(4-hydroxyphenyl)propionitrile

≥98% (HPLC)

Synonym(s):

DPN, Diarylpropionitrile, SC-4473

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About This Item

Empirical Formula (Hill Notation):
C15H13NO2
CAS Number:
1428-67-7
Molecular Weight:
239.27
MDL number:
MFCD01695412
UNSPSC Code:
51111800
PubChem Substance ID:
329815224
NACRES:
NA.77

sterility

non-sterile

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 10 mg/mL, clear

shipped in

ambient

storage temp.

−20°C

SMILES string

Oc1ccc(CC(C#N)c2ccc(O)cc2)cc1

InChI

1S/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

InChI key

GHZHWDWADLAOIQ-UHFFFAOYSA-N

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.

Features and Benefits

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H319,H400

Precautionary Statements

P273 - P305 + P351 + P338

Hazard Classifications

Aquatic Acute 1 - Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Chew Leng Lim et al.
eLife, 9 (2020-07-25)
There is strong evidence that the pro-inflammatory microenvironment during post-partum mammary involution promotes parity-associated breast cancer. Estrogen exposure during mammary involution drives tumor growth through neutrophils' activity. However, how estrogen and neutrophils influence mammary involution are unknown. Combined analysis of
L Hases et al.
Scientific reports, 10(1), 16160-16160 (2020-10-02)
There is a strong association between obesity and colorectal cancer (CRC), especially in men, whereas estrogen protects against both the metabolic syndrome and CRC. Colon is the first organ to respond to high-fat diet (HFD), and estrogen receptor beta (ERβ)
Konstantin Yakimchuk et al.
Endocrine connections, 7(12), 1472-1479 (2018-11-30)
Well-defined physiological functions of estrogens are mediated via nuclear estrogen receptors α (ESR1) and β (ESR2). With regard to hematological malignancies, expression of ESR2 has been found in both B and T cell lymphomas. In addition to endogenous estrogens or
Thomas J Lechuga et al.
Biology of reproduction, 100(2), 514-522 (2018-10-03)
Endogenous hydrogen sulfide (H2S) is a potent vasodilator and proangiogenic second messenger synthesized from L-cysteine by cystathionine β-synthase (CBS) and cystathionine γ-lyase (CTH). Estrogens are potent vasodilators that stimulate H2S biosynthesis in uterine arteries (UA) in vivo; however, the underlying
Luiz F Ferrari et al.
Scientific reports, 6, 31221-31221 (2016-08-09)
Hyperalgesic priming, an estrogen dependent model of the transition to chronic pain, produced by agonists at receptors that activate protein kinase C epsilon (PKCε), occurs in male but not in female rats. However, activation of second messengers downstream of PKCε
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