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Safety Information

SML1876

Sigma-Aldrich

PaPE-1

≥98% (HPLC)

Synonym(s):

(S)-5-(4-Hydroxy-3,5-dimethyl-phenyl)-indan-1-ol

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About This Item

Empirical Formula (Hill Notation):
C17H18O2
CAS Number:
2107327-36-4
Molecular Weight:
254.32
MDL number:
MFCD30723184
UNSPSC Code:
51111800
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 25 mg/mL, clear

storage temp.

2-8°C

SMILES string

O[C@H]1CCC2=C1C=CC(C3=CC(C)=C(O)C(C)=C3)=C2

InChI

1S/C17H18O2/c1-10-7-14(8-11(2)17(10)19)12-3-5-15-13(9-12)4-6-16(15)18/h3,5,7-9,16,18-19H,4,6H2,1-2H3/t16-/m0/s1

Biochem/physiol Actions

PaPE-1 is a "Pathway Preferential Estrogen" that activates the extranuclear signaling pathway without activating the nuclear signaling pathway. PaPE-1 bound 50,000-fold less well to ERα and Erβ estrogen receptors. PaPE-1 activated extranuclear-initiated ER-regulated genes, but showed essentially no activation of nuclear-initiated estrogen receptor (ER) gene targets such as the progesterone receptor. Unlike estradiol (E2), PaPE-1 did not stimulate proliferation of MCF-7 breast cancer cells. Like estradiol, PaPE-1 strongly activated MAPK and mTOR pathway. Instead, it showed preferential estrogen-like activity in non-reproductive (metabolic and vascular) tissues, reducing body weight gain and fat accumulation in ovariectomized mice and accelerating repair of endothelial damage in the vascualture.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

SML1876-VAR:
SML1876-5MG:
SML1876-BULK:
SML1876-25MG:

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Certificates of Analysis (COA)

Lot/Batch Number
017M4623V

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Zeynep Madak-Erdogan et al.
Science signaling, 9(429), ra53-ra53 (2016-05-26)
There is great medical need for estrogens with favorable pharmacological profiles that support desirable activities for menopausal women, such as metabolic and vascular protection, but that lack stimulatory activities on the breast and uterus. We report the development of structurally
Laura Marroqui et al.
Chemosphere, 265, 129051-129051 (2020-12-01)
Bisphenol-S (BPS) and Bisphenol-F (BPF) are current Bisphenol-A (BPA) substitutes. Here we used pancreatic β-cells from wild type (WT) and estrogen receptor β (ERβ) knockout (BERKO) mice to investigate the effects of BPS and BPF on insulin secretion, and the

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