2-Hydroxyestrone
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2-Hydroxyestrone
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CAS No:
362-06-1
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Formula:
C18H22O3
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Chemical Name:
2-Hydroxyestrone
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Synonyms:
Estra-1,3,5(10)-trien-17-one,2,3-dihydroxy-;2,3-Dihydroxyestra-1,3,5(10)-trien-17-one;2-Hydroxyestrone;Catecholestrone
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CAS No:
Description
Off-White to Tan Solid
Solid
2-hydroxyestrone is a 2-hydroxy steroid that is estrone substituted by a hydroxy group at position 2. It has a role as a human metabolite. It is a 2-hydroxy steroid and a member of catechols. It derives from an estrone.|2-Hydroxyestrone is a metabolite formed during the catabolism of estrone by the liver through the hydroxylation of the carbon at position 2 by cytochrome P450 (CYP) enzymes, including CYP1A1 and 1A2, with potential anticarcinogenic activity. The mechanism of action for the antitumor activity of 2-hydroxyestrone is not known but this metabolic product has minimal estrogenic activity compared to the parent compound and other estrone metabolites. Additionally, O-methylation of this compound produces 2-methoxyestradiol (2-MeOE2), which is a potent inhibitor of both cell proliferation and angiogenesis.
Characteristics
57.5
3.52300
Solid
1.241g/cm3
194-196 °C @ Solvent: Benzene
481.3ºC at 760 mmHg
259ºC
1.609
Safety Information
22-36
Xn
P201, P202, P281, P308+P313, P405, P501
H351
|Warning|H351 (100%): Suspected of causing cancer [Warning Carcinogenicity]|P201, P202, P281, P308+P313, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory.
Drug Information
Agents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved. (See all compounds classified as Anticarcinogenic Agents.)
2-hydroxyestrone has known human metabolites that include 2-Methoxyestrone, 3-O-methoxyestrone, and Estrone 2-O-glucuronide.
2-hydroxyestrone
2-Hydroxyestrone Use and Manufacturing
A metabolite of Estradiol
Lipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C18 steroids (estrogens) and derivatives [ST0201]
Computed Properties
Molecular Weight:286.4
XLogP3:2.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Exact Mass:286.15689456
Monoisotopic Mass:286.15689456
Topological Polar Surface Area:57.5
Heavy Atom Count:21
Complexity:448
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes