4-hydroxyestradiol

Names

[ Name ]:
4-hydroxyestradiol

[Synonym ]:
4-Hydroxy-17β-estradiol
MFCD00063335
4-HYDROXYESTRADIOL
4-hydroxy-17beta-estradiol

Biological Activity

[Description]:

4-Hydroxyestradiol (4-Hydroxy-17β-estradiol) is an endogenous metabolite of Estradiol (HY-B0141). 4-Hydroxyestradiol is carcinogenic and shows mutagenic activity in breast epithelial cells. 4-Hydroxyestradiol inhibits the binding of Estradiol to the estrogen receptor in a competitive manner, with a Ki of 0.48 nM[1][2].

[Related Catalog]:

Research Areas >> Cancer

[References]

[1]. Fernandez SV, et al. Estradiol and its metabolites 4-hydroxyestradiol and 2-hydroxyestradiol induce mutations in human breast epithelial cells. Int J Cancer. 2006 Apr 15;118(8):1862-8. doi: 10.1002/ijc.21590.

[2]. Van Aswegen CH, 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.

Chemical & Physical Properties

[ Density]:
1.248g/cm3

[ Boiling Point ]:
468.6ºC at 760 mmHg

[ Melting Point ]:
>210ºC (dec.)

[ Molecular Formula ]:
C₁₈H₂₄O₃

[ Molecular Weight ]:
288.38100

[ Flash Point ]:
220.6ºC

[ Exact Mass ]:
288.17300

[ PSA ]:
60.69000

[ LogP ]:
3.31480

[ Index of Refraction ]:
1.622

[ Storage condition ]:
−20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: KG7676000

CHEMICAL NAME :: Estra-1,3,5(10)-triene-3,4,17-beta-triol

CAS REGISTRY NUMBER :: 5976-61-4

LAST UPDATED :: 199712

DATA ITEMS CITED :: 4

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 :: Implant

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 900 mg/kg/90D-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Kidney, Ureter, Bladder - Kidney tumors

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

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

MUTATION DATA

TEST SYSTEM :: Rodent - hamster

DOSE/DURATION :: 14 mg/kg/7D (Continuous)

REFERENCE :: CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House, Southfield Road, Eynsham, Oxford OX8 1JJ, UK) V.1- 1980- Volume(issue)/page/year: 15,997,1994

Safety Information

[ Symbol ]:

GHS08

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H351

[ Precautionary Statements ]:
P281

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
40

[ Safety Phrases ]:
S22;S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
KG7676000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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Related Compounds

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