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SML1355

PHTPP

Name: PHTPP
Brand: SIGMA

≥98% (HPLC), estrogen receptor β antagonist, powder

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

UNSPSC Code:

51111800

PubChem Substance ID:

329825810

NACRES:

NA.77

MDL number:

MFCD09971112

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

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Product Name

PHTPP, ≥98% (HPLC)

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

Related Categories

Bioactive Small Molecules

Biochem/physiol Actions

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).

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 a selective estrogen receptor β (ERβ) full antagonist.

pictograms

GHS06

signalword

Danger

hcodes

H301

pcodes

P264 - P270 - P301 + P310 - P405 - P501

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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

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Repeated Exposure to 4-Methyl-2,4-bis(4-hydroxyphenyl)pent-1-ene (MBP), an Active Metabolite of Bisphenol A, Aggressively Stimulates Breast Cancer Cell Growth in an Estrogen Receptor β (ERβ)-Dependent Manner.

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

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)

Estrogen receptor beta mediates hepatotoxicity induced by perfluorooctane sulfonate in mouse.

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

Estrogen prevent atherosclerosis by attenuating endothelial cell pyroptosis via activation of estrogen receptor α-mediated autophagy.

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

Estrogen receptor β upregulates CCL2 via NF-κB signaling in endometriotic stromal cells and recruits macrophages to promote the pathogenesis of endometriosis.

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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Global Trade Item Number

SKU	GTIN
SML1355-25MG	04061832868516
SML1355-5MG	04061837107863

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