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4-hydroxy Estrone

(Synonyms: 4-羟基雌酮; 4-OHE1) 目录号 : GC48824

A metabolite of estrone

4-hydroxy Estrone Chemical Structure

Cas No.:3131-23-5

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产品描述

4-hydroxy Estrone is a metabolite of the endogenous estrogen estrone .1 It is formed from estrone primarily by the cytochrome P450 (CYP) isoforms CYP1B1, CYP1A2, and CYP1A1. 4-hydroxy Estrone (5 µM) induces nuclear translocation of phosphorylated p53 and is protective against glutamate-induced oxidative death in HT22 hippocampal neuronal cells.2 It reduces neurodegeneration induced by kainic acid in the rat hippocampus and improves working memory in the Y-maze in rats when administered at a dose of 10 µg/animal. 4-hydroxy Estrone also inhibits proliferation of MCF-7 and MDA-MB-231 breast cancer cells with IC50 values of 30 and 38 µM, respectively.3

1.Cribb, A.E., Knight, M.J., Dryer, D., et al.Role of polymorphic human cytochrome P450 enzymes in estrone oxidationCancer Epidemiol. Biomarkers Prev.15(3)551-558(2006) 2.Choi, H.J., Lee, A.J., Kang, K.S., et al.4-Hydroxyestrone, an endogenous estrogen metabolite, can strongly protect neuronal cells against oxidative damageSci. Rep.10(1)7283(2020) 3.Seeger, H., Huober, J., Wallwiener, D., et al.Inhibition of human breast cancer cell proliferation with estradiol metabolites is as effective as with tamoxifenHorm. Metab. Res.36(5)277-280(2004)

Chemical Properties

Cas No. 3131-23-5 SDF
别名 4-羟基雌酮; 4-OHE1
Canonical SMILES C[C@@]12[C@](CCC2=O)([H])[C@@]3([H])[C@@](CC1)([H])C4=CC=C(O)C(O)=C4CC3
分子式 C18H22O3 分子量 286.4
溶解度 DMSO: slightly soluble,Ethanol: slightly, sonicated 储存条件 -20°C
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1 mg 5 mg 10 mg
1 mM 3.4916 mL 17.4581 mL 34.9162 mL
5 mM 0.6983 mL 3.4916 mL 6.9832 mL
10 mM 0.3492 mL 1.7458 mL 3.4916 mL
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Research Update

Occurrence, seasonal variation and risk evaluation of selected endocrine disrupting compounds and their transformation products in Jiulong river and estuary, China

Mar Pollut Bull 2019 Aug;145:370-376.PMID:31590799DOI:10.1016/j.marpolbul.2019.05.016.

In the present study, 13 endocrine disrupting compounds (EDCs) and their transformation products (TPs) were monitored in Jiulong River and its estuary, China in different seasons. The analytes included antimicrobials [triclosan (TCS) and triclocarbon (TCC)]; estrogens [estrone (E1), estradiol (E2), estriol (E3) and ethinylestradiol (EE2)]; alkylphenol ethoxylates [4-n-nonylphenol (NP) and 4-n-octylphenol (OP)] and the TPs [methyl triclosan (MeTCS), carbanilide (NCC), dichlorocarbanilide, 4-hydroxy Estrone (4-OH E1) and 4-hydroxy estradiol (4-OH E2)]. A significant seasonal variation was observed for most EDCs. Approximately, 79% of the total E2 residues were detected in the normal season in comparison with the wet season to indicate recalcitrant behavior of E2 during the normal season. Risk assessment revealed that E2 was most potent among the EDCs to cause highest risk to both vertebrate and invertebrate aquatic species, whereas, E1, EE2, MeTCS and TCS also showed relatively high risk for some surface water aquatic species.