4-HYDROXYESTRADIOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H24O3
Molecular Weight	288.3814
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@]12CC[C@H]3[C@@H](CCC4=C(O)C(O)=CC=C34)[C@@H]1CC[C@@H]2O

InChI

InChIKey=QOZFCKXEVSGWGS-ZHIYBZGJSA-N

InChI=1S/C18H24O3/c1-18-9-8-11-10-4-6-15(19)17(21)13(10)3-2-12(11)14(18)5-7-16(18)20/h4,6,11-12,14,16,19-21H,2-3,5,7-9H2,1H3/t11-,12-,14+,16+,18+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C18H24O3
Molecular Weight	288.3814
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Preferential growth stimulation of mammary glands over uterine endometrium in female rats by a naturally occurring estradiol-17beta-fatty acid ester.	2001 Aug 1	11479213
In situ hybridization and immunohistochemical analysis of cytochrome P450 1B1 expression in human normal tissues.	2001 Feb	11156691
Gas chromatographic determination of catecholestrogens following isolation by solid-phase extraction.	2001 Jul 15	11486823
Analysis of potential biomarkers of estrogen-initiated cancer in the urine of Syrian golden hamsters treated with 4-hydroxyestradiol.	2001 Jun	11375897
In vitro generation of peroxynitrite by 2- and 4-hydroxyestrogens in the presence of nitric oxide.	2001 May	11368553
Catecholestrogen sulfation: possible role in carcinogenesis.	2002 Mar 29	11906176
The cancer preventative agent resveratrol is converted to the anticancer agent piceatannol by the cytochrome P450 enzyme CYP1B1.	2002 Mar 4	11875742
Characterization of human soluble high and low activity catechol-O-methyltransferase catalyzed catechol estrogen methylation.	2002 Oct	12360102
Endogenous estradiol metabolites stimulate the in vitro proliferation of human osteoblastic cells.	2003 Apr	12708603
Increased estrogen formation and estrogen to androgen ratio in the synovial fluid of patients with rheumatoid arthritis.	2003 Dec	14719200
Sequential action of phase I and II enzymes cytochrome p450 1B1 and glutathione S-transferase P1 in mammary estrogen metabolism.	2003 Dec 1	14679015
2-Methoxyestradiol, a promising anticancer agent.	2003 Feb	12587805
Medical hypothesis: hyperhomocysteinemia is a risk factor for estrogen-induced hormonal cancer.	2003 Mar	12579301
A gas chromatography/mass spectrometry assay to measure estradiol, catecholestradiols, and methoxyestradiols in plasma.	2004 Apr	15183691
Lack of association of CYP1 B1*3 polymorphism and ovarian cancer in a Caucasian population.	2004 Apr-Jun	15255550
Microsomal estrogen metabolism in channel catfish.	2004 Aug-Dec	15178071
Metabolism and DNA binding studies of 4-hydroxyestradiol and estradiol-3,4-quinone in vitro and in female ACI rat mammary gland in vivo.	2004 Feb	14578156
Dietary indole-3-carbinol promotes endometrial adenocarcinoma development in rats initiated with N-ethyl-N'-nitro-N-nitrosoguanidine, with induction of cytochrome P450s in the liver and consequent modulation of estrogen metabolism.	2004 Nov	15240508
In vitro model of mammary estrogen metabolism: structural and kinetic differences between catechol estrogens 2- and 4-hydroxyestradiol.	2004 Sep	15377160
Mitogenic estrogen metabolites alter the expression of 17beta-estradiol-regulated proteins including heat shock proteins in human MCF-7 breast cancer cells.	2005 Dec 31	16404153
Invasiveness of breast cancer cells MDA-MB-231 through extracellular matrix is increased by the estradiol metabolite 4-hydroxyestradiol.	2005 Feb 20	15499624
Effect of catecholestrogen administration during adriamycin-induced cardiomyopathy in ovariectomized rat.	2005 Sep	16087475
Estradiol and its metabolites 4-hydroxyestradiol and 2-hydroxyestradiol induce mutations in human breast epithelial cells.	2006 Apr 15	16287077
Comparison of possible carcinogenic estradiol metabolites: effects on proliferation, apoptosis and metastasis of human breast cancer cells.	2006 Apr 20	16213115
Catechol estrogen quinones as initiators of breast and other human cancers: implications for biomarkers of susceptibility and cancer prevention.	2006 Aug	16675129
Regioselective 2-hydroxylation of 17beta-estradiol by rat cytochrome P4501B1.	2006 Nov 1	16893557
Potential biomarker for early risk assessment of prostate cancer.	2006 Oct 1	16894534
Etheno-DNA adduct formation in rats gavaged with linoleic acid, oleic acid and coconut oil is organ- and gender specific.	2007 Nov 1	17521682
HPLC for stress-free screening of potential prostate cancer marker catechol estrogens in urine using a diamond-electrode electrochemical and a fluorescence detector.	2007 Sep	17668912
Soy isoflavones decrease the catechol-O-methyltransferase-mediated inactivation of 4-hydroxyestradiol in cultured MCF-7 cells.	2008 Feb	18192686
Reduction of estrogen-induced transformation of mouse mammary epithelial cells by N-acetylcysteine.	2008 Mar	18226522
Leu432Val polymorphism in CYP1B1 as a susceptible factor towards predisposition to primary open-angle glaucoma.	2008 May 8	18483560
Hydroxyestrogens inhibit angiogenesis in swine ovarian follicles.	2008 Oct	18662972
CYP1B1 variants are associated with prostate cancer in non-Hispanic and Hispanic Caucasians.	2008 Sep	18544568

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:53:51 GMT 2025` Edited by `admin` on `Mon Mar 31 17:53:51 GMT 2025`
Record UNII	C3ZO03450E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

1,3,5(10)-ESTRATRIENE-3,4,17.BETA.-TRIOL

Preferred Name

English

4-HYDROXYESTRADIOL

Common Name

English

ESTRADIOL METABOLITE (4-HYDROXYESTRADIOL)

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C347