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SML1355

Sigma-Aldrich

PHTPP

≥98% (HPLC)

Synonym(s):

2-Phenyl-3-(4-hydroxyphenyl)-5,7-bis(trifluoromethyl)-pyrazolo[1,5-a]pyrimidine, 4-[2-Phenyl-5,7-bis(trifluoromethyl)pyrazolo[1,5-a]-pyrimidin-3-yl]phenol

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About This Item

Empirical Formula (Hill Notation):
C20H11F6N3O
CAS Number:
805239-56-9
Molecular Weight:
423.31
MDL number:
MFCD09971112
UNSPSC Code:
51111800
PubChem Substance ID:
329825810
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

yellow to orange

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

OC(C=C1)=CC=C1C(C(C2=CC=CC=C2)=N3)=C4N3C(C(F)(F)F)=CC(C(F)(F)F)=N4

InChI

1S/C20H11F6N3O/c21-19(22,23)14-10-15(20(24,25)26)29-18(27-14)16(11-6-8-13(30)9-7-11)17(28-29)12-4-2-1-3-5-12/h1-10,30H

InChI key

AEZPAUSGTAHLOQ-UHFFFAOYSA-N

Biochem/physiol Actions

PHTPP is a selective estrogen receptor β (ERβ) full antagonist with 36-fold selectivity for ERβ over ERα. PHTPP has been used to distinguish the various activites of the two estrogen receptors. Estrogen can have opposite effects in some tumors expressing ERα compared to Erβ, with Erα enhancing and Erβ suppressing tumor cell growth. PHTPP, a selective ERβ antagonist, significantly enhanced cell growth in ovarian cancer cell lines SKOV3 and OV2008 that express both receptors.
PHTPP is also termed as 4-[2–phenyl-5,7–bis (trifluoromethyl) pyrazolo [1,5-a]-pyrimidin-3-yl] phenol (PHTPP). It blocks hypoglycemic augmentation of norepinephrine (NE) in the hypothalamic arcuate (ARH).

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Hindbrain estrogen receptor-beta antagonism normalizes reproductive and counter-regulatory hormone secretion in hypoglycemic steroid-primed ovariectomized female rats.
Briski KP and Shrestha PK
Neuroscience, 331, 62-71 (2016)
Masayo Hirao-Suzuki et al.
Molecular pharmacology, 95(3), 260-268 (2018-12-16)
Bisphenol A (BPA), recognized as an endocrine disruptor, is thought to exert its activity through a mechanism involving the activation of estrogen receptors (ERs) α/β However, a major problem is that very high concentrations of BPA are required (i.e., those
Cheng Xu et al.
Environmental science and pollution research international, 24(15), 13414-13423 (2017-04-08)
Perfluorooctane sulfonate (PFOS), an artificial fluorosurfactant and global contaminant, is used widely in various consumer products. In this study, we investigated the function of estrogen receptor β (ERβ) in PFOS-induced bile acid and cholesterol metabolism disorders and gut microbiome using
Qinghai Meng et al.
Journal of advanced research, 28, 149-164 (2020-12-29)
Excessive inflammation and the pyroptosis of vascular endothelial cells caused by estrogen deficiency is one cause of atherosclerosis in post-menopausal women. Because autophagy is highly regulated by estrogen, we hypothesized that estrogen can reduce vascular endothelial cell pyroptosis through estrogen
Yanling Gou et al.
Human reproduction (Oxford, England), 34(4), 646-658 (2019-03-07)
How is the activation of estrogen receptor β (ERβ) in endometriotic stromal cells (ESCs) involved in macrophage recruitment to promote the pathogenesis of endometriosis? ERβ modulates the production of C-C motif chemokine ligand 2 (CCL2) via nuclear factor kappa-light-chain-enhancer of
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