2-hydroxyestrone

Modify Date: 2025-08-25 10:54:27

2-hydroxyestrone Structure
2-hydroxyestrone structure
Common Name 2-hydroxyestrone
CAS Number 362-06-1 Molecular Weight 286.36500
Density 1.241g/cm3 Boiling Point 481.3ºC at 760 mmHg
Molecular Formula C18H22O3 Melting Point 199-201ºC
MSDS N/A Flash Point 259ºC

 Use of 2-hydroxyestrone


2-Hydroxyestrone (Catecholestrone) is a specific receptor-mediated antiestrogenic agent. 2-Hydroxyestrone is anticarcinogenic[1][2].

 Names

Name 2-hydroxyestrone
Synonym More Synonyms

 2-hydroxyestrone Biological Activity

Description 2-Hydroxyestrone (Catecholestrone) is a specific receptor-mediated antiestrogenic agent. 2-Hydroxyestrone is anticarcinogenic[1][2].
Related Catalog
Target

Human Endogenous Metabolite

Estrogen receptor

In Vitro 2-Hydroxyestrone exhibits antiestrogen action on MCF-7 human breast cancer cells. Addition of 2-Hydroxyestrone to the cell cultures in concentration of 1-1000 nM has no effect on cell growth and proliferation because of rapid O-methylation of the catechol estrogen by catechol O-methyltransferase which is highly active in these cells. In the presence of quinalizarin, a potent catechol O-methyltransferase inhibitor which reduces the O-methylation of the steroid, 10 and 100 nM 2-Hydroxyestrone markedly suppresses the growth and proliferation of the cells[2]. Cell Proliferation Assay[2] Cell Line: Human breast cancer cell lines MCF-7, MDA-MB-231, and MDA-MB-330 Concentration: 1-1000 nM Incubation Time: 6 days Result: 10 and 100 nM markedly suppressed the growth and proliferation of the cells in the presence of quinalizarin. The tumor cell growth-inhibitory action of the catechol estrogen was neutralized by the presence of 1 nM estradiol.
In Vivo Levels of both 2-Hydroxyestrone (2-OHE1; 2 mg/kg; administered ip.) and  2-Hydroxyestrone 4-N-acetylcysteine thioether (2-OHE1 4SR) in rats treated with 2-Hydroxyestrone were significantly different between the induced and noninduced groups[3]. Animal Model: Female and male Sprague-Dawley rats (6 weeks old)[3] Dosage: 2 mg/kg Administration: Administered i.p. Result: Levels of both 2-OHE1 and  2-OHE1 4SR in rats treated with 2-OHE1 were significantly different between the induced and noninduced groups.
References

[1]. H L Bradlow, et al. 2-Hydroxyestrone: the 'good' estrogen. J Endocrinol. 1996 Sep;150 Suppl:S259-65.

[2]. J Schneider, et al. Antiestrogen action of 2-Hydroxyestrone on MCF-7 human breast cancer cells. J Biol Chem. 1984 Apr 25;259(8):4840-5.

[3]. M Nakagomi, et al. Quantitation of catechol estrogens and their N-acetylcysteine conjugates in urine of rats and hamsters. Chem Res Toxicol. 2000 Dec;13(12):1208-13.

 Chemical & Physical Properties

Density 1.241g/cm3
Boiling Point 481.3ºC at 760 mmHg
Melting Point 199-201ºC
Molecular Formula C18H22O3
Molecular Weight 286.36500
Flash Point 259ºC
Exact Mass 286.15700
PSA 57.53000
LogP 3.52300
Index of Refraction 1.609
Storage condition 2-8°C

 Safety Information

Hazard Codes Xi

 Synonyms

3-Methoxypicolinimidamidehydrochloride
3-O-Methyl 17|A-Estradiol
2-hydroxyestron
2-Hydroxyestrone
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