4-hydroxyestrone

Names

[ Name ]:
4-hydroxyestrone

[Synonym ]:
4-Hydroxy Estrone
MFCD00079358
(8R,9S,13S,14S)-3,4-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
4-HydroxyEstrone

Biological Activity

[Description]:

4-Hydroxyestrone (4-OHE1), an estrone metabolite, has strong neuroprotective effect against oxidative neurotoxicity. 4-Hydroxyestrone increases cytoplasmic translocation of p53 resulting from SIRT1-mediated deacetylation of p53. 4-Hydroxyestrone has little estrogenic activity[1].

[Related Catalog]:

Research Areas >> Neurological Disease

[Target]

Human Endogenous Metabolite

[References]

[1]. Hye Joung Choi, et al. 4-Hydroxyestrone, an Endogenous Estrogen Metabolite, Can Strongly Protect Neuronal Cells Against Oxidative Damage. Sci Rep. 2020 Apr 29;10(1):7283.

Chemical & Physical Properties

[ Density]:
1.241g/cm3

[ Boiling Point ]:
468.2ºC at 760mmHg

[ Melting Point ]:
260-263ºC

[ Molecular Formula ]:
C₁₈H₂₂O₃

[ Molecular Weight ]:
286.36500

[ Flash Point ]:
251.1ºC

[ Exact Mass ]:
286.15700

[ PSA ]:
57.53000

[ LogP ]:
3.52300

[ Index of Refraction ]:
1.61

[ Storage condition ]:
2-8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: KG7749500

CHEMICAL NAME :: Estra-1,3,5(10)-trien-17-one, 3,4-dihydroxy-

CAS REGISTRY NUMBER :: 3131-23-5

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C18-H22-O3

MOLECULAR WEIGHT :: 286.40

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 30 mg/kg

SEX/DURATION :: female 1-6 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

REFERENCE :: STEDAM Steroids. (Holden-Day Inc., 4432 Telegraph Ave., Oakland, CA 94609) V.1- 1963- Volume(issue)/page/year: 30,343,1977

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
KG7749500

Precursor & DownStream

Precursor

DownStream

Articles

Improved profiling of estrogen metabolites by orbitrap LC/MS.

Steroids 99 , 84-90, (2015)

Estrogen metabolites are important biomarkers to evaluate cancer risks and metabolic diseases. Due to their low physiological levels, a sensitive and accurate method is required, especially for the qu...

Redox cycling of catechol estrogens generating apurinic/apyrimidinic sites and 8-oxo-deoxyguanosine via reactive oxygen species differentiates equine and human estrogens.

Chem. Res. Toxicol. 23(8) , 1365-73, (2010)

Metabolic activation of estrogens to catechols and further oxidation to highly reactive o-quinones generates DNA damage including apurinic/apyrimidinic (AP) sites. 4-Hydroxyequilenin (4-OHEN) is the m...

Menstrual cycle effects on urinary estrogen metabolites.

J. Clin. Endocrinol. Metab. 84(11) , 3914-8, (1999)

Endogenous estrogen metabolism may play an important role in the pathogenesis of hormone-related cancers, most notably breast cancer. Despite the importance of estrogen metabolism, little is known abo...