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2-羟基-17β-雌二醇

2-羟基-17β-雌二醇用途

2-羟基雌二醇是17β-雌二醇的代谢产物,具有最低的雌激素活性,具有抗氧化作用,与DNA反应形成稳定的加合物,并具有遗传毒性[1][3]。

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2-羟基-17β-雌二醇名称

[ CAS 号 ]:
362-05-0

[ 中文名 ]:
雌甾-1,3,5(10)-三烯2,3,17-三醇

[ 英文名 ]:
2-Hydroxyestradiol

[中文别名 ]:

[英文别名 ]:

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)-

2-羟基-17β-雌二醇生物活性

[ 描述 ]:

2-羟基雌二醇是17β-雌二醇的代谢产物,具有最低的雌激素活性,具有抗氧化作用,与DNA反应形成稳定的加合物,并具有遗传毒性[1][3]。

[ 相关类别 ]:

信号通路 >> 其他 >> 其他

研究领域 >> 代谢疾病

[体外研究]

2-羟基雌二醇诱导指示肿瘤转化的表型变化[1]。2-羟基雌二醇(2-OHE2)能够在体外转化HBEC、MCF-10F细胞系,即雌激素受体a(ERα)阴性和ERβ阳性[1]。2-羟基雌二醇诱导人乳腺上皮细胞DNA氧化损伤和凋亡[3]。

[体内研究]

2-羟基雌二醇可以减轻肥胖的发展,改善内皮功能,减少肾病,降低糖尿病的严重程度,降低动脉血压,降低血浆胆固醇[2]。

[参考文献]

[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.

2-羟基-17β-雌二醇物理化学性质

[ 密度 ]:
1.2±0.1 g/cm3

[ 沸点 ]:
481.5±45.0 °C at 760 mmHg

[ 熔点 ]:
96-104°C

[ 分子式 ]:
C₁₈H₂₄O₃

[ 分子量 ]:
288.38

[ 闪点 ]:
227.6±23.3 °C

[ 精确质量 ]:
288.172546

[ PSA ]:
60.69000

[ LogP ]:
3.53

[ 蒸汽压 ]:
0.0±1.3 mmHg at 25°C

[ 折射率 ]:
1.622

[ 储存条件 ]:
−20°C

2-羟基-17β-雌二醇MSDS

2-羟基-17β-雌二醇毒性和生态

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

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2-羟基-17β-雌二醇安全信息

[ 符号 ]:

GHS08

[ 信号词 ]:
Warning

[ 危害声明 ]:
H351

[ 警示性声明 ]:
P281

[ 个人防护装备 ]:
dust mask type N95 (US);Eyeshields;Gloves

[ 危害码 (欧洲) ]:
Xn: Harmful;

[ 风险声明 (欧洲) ]:
40

[ 安全声明 (欧洲) ]:
S22;S36

[ 危险品运输编码 ]:
NONH for all modes of transport

[ WGK德国 ]:
3

[ RTECS号 ]:
KG7675000

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2-羟基-17β-雌二醇文献

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...

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