2-Hydroxyestradiol

Names

[ CAS No. ]:
362-05-0

[ Name ]:
2-Hydroxyestradiol

[Synonym ]:
Estra-1,3,5(10)-triene-2,3,17β-triol
2-Hydroxy-17b-estradiol
2-hydroxy-17β-estradiol
2-hydroxy-17beta-estradiol
MFCD00010490
(17β)-Estra-1(10),2,4-triene-2,3,17-triol
Estra-1,3,5(10)-triene-2,3,17-triol, (17β)-
2-Hydroxyestradiol
2,3,17b-Trihydroxyestra-1,3,5(10)-triene
estra-1(10),2,4-triene-2,3,17-triol, (17β)-
Estra-1,3,5(10)-triene-2,3,17-β-triol
(17b)-Estra-1(10),2,4-triene-2,3,17-triol
(17β)-Estra-1,3,5(10)-triene-2,3,17-triol
2-hydroxy-estradiol
2-Oh-estradiol
Estra-1,3,5(10)-triene-2,3,17b-triol
2-Hydroxy-17-estradiol

Biological Activity

[Description]:

2-Hydroxyestradiol, a metabolite of 17β-estradiol with minimal estrogenic activity, possesses antioxidant effects and reacts with DNA to form stable adducts and exerts genotoxicity[1][3].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Metabolic Disease

[In Vitro]

2-Hydroxyestradiol induces phenotypical changes indicative of neoplastic transformation[1]. 2-Hydroxyestradiol (2-OHE2) is capable of in vitro transforming a HBEC, MCF-10F cell line, that is estrogen receptor-a (ERα) negative and ERβ positive[1]. 2-Hydroxyestradiol induces oxidative DNA damage and apoptosis in human mammary epithelial cells[3].

[In Vivo]

2-Hydroxyestradiol attenuated the development of obesity and improved endothelial function, decreased nephropathy, decreased the severity of diabetes, lowered arterial blood pressure, and reduced plasma cholesterol[2].

[References]

[1]. C H Van Aswegen, et al. Binding of 2-hydroxyestradiol and 4-hydroxyestradiol to estrogen receptors from human breast cancers. J Steroid Biochem. 1989 Apr;32(4):485-92.

[2]. S P Tofovic, et al. 2-Hydroxyestradiol attenuates the development of obesity, the metabolic syndrome, and vascular and renal dysfunction in obese ZSF1 rats. J Pharmacol Exp Ther. 2001 Dec;299(3):973-7.

[3]. Yeon-Jin Hurh, et al. 2-Hydroxyestradiol induces oxidative DNA damage and apoptosis in human mammary epithelial cells. J Toxicol Environ Health A. 2004 Dec;67(23-24):1939-53.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
481.5±45.0 °C at 760 mmHg

[ Melting Point ]:
96-104°C

[ Molecular Formula ]:
C₁₈H₂₄O₃

[ Molecular Weight ]:
288.38

[ Flash Point ]:
227.6±23.3 °C

[ Exact Mass ]:
288.172546

[ PSA ]:
60.69000

[ LogP ]:
3.53

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.622

[ Storage condition ]:
−20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: KG7675000

CHEMICAL NAME :: Estra-1,3,5(10)-triene-2,3,17-beta-triol

CAS REGISTRY NUMBER :: 362-05-0

BEILSTEIN REFERENCE NO. :: 2219367

LAST UPDATED :: 199709

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C18-H24-O3

MOLECULAR WEIGHT :: 288.42

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 1280 ng/kg

SEX/DURATION :: male 8 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - other effects on male Endocrine - androgenic

REFERENCE :: ANDRDQ Andrologia. (Grosse Verlag GmbH, Kurfuerstenstr. 112-113, D-1000 Berlin 30, Fed. Rep. Ger.) V.6- 1974- Volume(issue)/page/year: 23,339,1991

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 10 ug/kg

SEX/DURATION :: female 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina

REFERENCE :: EXPEAM Experientia. (Birkhaeuser Verlag, POB 133, CH-4010 Basel, Switzerland) V.1- 1945- Volume(issue)/page/year: 42,165,1986

Safety Information

[ Symbol ]:

GHS08

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H351

[ Precautionary Statements ]:
P281

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
40

[ Safety Phrases ]:
S22;S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
KG7675000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

A methoxyflavonoid, chrysoeriol, selectively inhibits the formation of a carcinogenic estrogen metabolite in MCF-7 breast cancer cells.

J. Steroid Biochem. Mol. Biol. 118(1-2) , 70-6, (2010)

A 17beta-estradiol (E(2)) is hydrolyzed to 2-hydroxy-E(2) (2-OHE(2)) and 4-hydroxy-E(2) (4-OHE(2)) via cytochrome P450 (CYP) 1A1 and 1B1, respectively. In estrogen target tissues including the mammary...

Impact of induced fit on ligand binding to the androgen receptor: a multidimensional QSAR study to predict endocrine-disrupting effects of environmental chemicals.

J. Med. Chem. 48 , 5666-74, (2005)

We investigated the influence of induced fit of the androgen receptor binding pocket on free energies of ligand binding. On the basis of a novel alignment procedure using flexible docking, molecular d...

Norethisterone acetate alters coagulation gene expression in vitro in human cell culture.

Thromb. Res. 131(1) , 72-7, (2013)

Both oestrogen and progestin and the route of administration have been implicated in cardiovascular and thromboembolic risk in post menopausal hormone users. Transdermal preparations have been reporte...