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雌三醇

雌三醇用途

Estriol是G蛋白偶联雌激素受体拮抗剂,可作用于雌激素受体阴性乳腺癌细胞。

雌三醇名称

[ CAS 号 ]:
50-27-1

[ 中文名 ]:
雌三醇

[ 英文名 ]:
Estriol

[中文别名 ]:

[英文别名 ]:

16α-Estriol
OVESTIN
TRIOVEX
(16a,17b)-Estra-1,3,5(10)-triene-3,16,17-triol
16a-Hydroxyestradiol
Tridestrin
Oestriol
Thulol
Ovo-Vinces
Colpogyn

雌三醇生物活性

[ 描述 ]:

Estriol是G蛋白偶联雌激素受体拮抗剂,可作用于雌激素受体阴性乳腺癌细胞。

[ 相关类别 ]:

信号通路 >> 其他 >> 雌激素受体/ERR

天然产物 >> 其他

研究领域 >> 癌症

[ 靶点 ]

Human Endogenous Metabolite

[参考文献]

[1]. Morinaga, A., et al., Effects of sex hormones on Alzheimer's disease-associated beta-amyloid oligomer formation in vitro. Exp Neurol, 2011. 228(2): p. 298-302.

[2]. Begum, M., et al., Neonatal estrogenic exposure suppresses PTEN-related endometrial carcinogenesis in recombinant mice. Lab Invest, 2006. 86(3): p. 286-96.

[3]. Hewitt, S.C. and K.S. Korach, Estrogenic activity of bisphenol A and 2,2-bis(p-hydroxyphenyl)-1,1,1-trichloroethane (HPTE) demonstrated in mouse uterine gene profiles. Environ Health Perspect, 2011. 119(1): p. 63-70.

[相关活性小分子]

雌三醇物理化学性质

[ 密度 ]:
1.3±0.1 g/cm3

[ 沸点 ]:
469.0±45.0 °C at 760 mmHg

[ 熔点 ]:
280-282 °C(lit.)

[ 分子式 ]:
C₁₈H₂₄O₃

[ 分子量 ]:
288.381

[ 闪点 ]:
220.8±23.3 °C

[ 精确质量 ]:
288.172546

[ PSA ]:
60.69000

[ LogP ]:
2.94

[ 外观性状 ]:
白色结晶粉末

[ 蒸汽压 ]:
0.0±1.2 mmHg at 25°C

[ 折射率 ]:
1.624

[ 储存条件 ]:
-20°C Freezer

[ 水溶解性 ]:
水溶性：不溶；可溶于：甲醇；微溶：二噁烷,乙醇；不溶：乙醚

雌三醇MSDS

雌三醇毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: KG8225000

CHEMICAL NAME :: Estriol

CAS REGISTRY NUMBER :: 50-27-1

BEILSTEIN REFERENCE NO. :: 2508172

LAST UPDATED :: 199612

DATA ITEMS CITED :: 31

MOLECULAR FORMULA :: C18-H24-O3

MOLECULAR WEIGHT :: 288.42

WISWESSER LINE NOTATION :: L E5 B666TTT&J E1 FQ GQ OQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Implant

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 26 mg/kg

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Skin and Appendages - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Implant

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 20 mg/kg

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Reproductive - Tumorigenic effects - uterine tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Implant

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 480 mg/kg/64W-C

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

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Implant

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 34 mg/kg

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Skin and Appendages - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 17500 ug/kg

SEX/DURATION :: female 35 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 3 mg/kg

SEX/DURATION :: female 1-4 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 577 ug/kg

SEX/DURATION :: female 16-19 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - urogenital system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 8440 ng/kg

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

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 5 mg/kg

SEX/DURATION :: female 5 day(s) after conception

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 250 ug/kg

SEX/DURATION :: female 4-8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 50 ug/kg

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

TOXIC EFFECTS :: Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Fertility - abortion

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 350 ug/kg

SEX/DURATION :: female 7 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Effects on Newborn - stillbirth

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 500 ug/kg

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

TOXIC EFFECTS :: Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Maternal Effects - uterus, cervix, vagina Reproductive - Fertility - other measures of fertility

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 400 ug/kg

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

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 85 ug/kg

SEX/DURATION :: female 7 day(s) pre-mating female 1-10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Parenteral

DOSE :: 105 ug/kg

SEX/DURATION :: female 1-7 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intrauterine

DOSE :: 1500 ng/kg

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

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 100 mg/kg

SEX/DURATION :: male 10 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 60 ug/kg

SEX/DURATION :: female 1-3 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 25 ug/kg

SEX/DURATION :: female 1-3 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - other measures of fertility

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intrauterine

DOSE :: 760 ng/kg

SEX/DURATION :: female 28 day(s) pre-mating female 1-10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 3200 ug/kg

SEX/DURATION :: female 2-5 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)

MUTATION DATA

TYPE OF TEST :: Sex chromosome loss and nondisjunction

TEST SYSTEM :: Rodent - hamster Fibroblast

DOSE/DURATION :: 75 umol/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 171,31,1986 *** REVIEWS *** IARC Cancer Review:Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 21,327,1979 TOXICOLOGY REVIEW CANCAR Cancer (Philadelphia). (Lippincott/Harper, Journal Fulfillment Dept., 2350 Virginia Ave., Hagerstown, MD 21740) V.1- 1948- Volume(issue)/page/year: 40,1825,1977 TOXICOLOGY REVIEW CLECAP Clinical Endocrinology (Oxford). (Blackwell Scientific Pub. Ltd., POB 88, Oxford, UK) V.1- 1972- Volume(issue)/page/year: 4,551,1975 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 80409 No. of Facilities: 68 (estimated) No. of Industries: 1 No. of Occupations: 6 No. of Employees: 2770 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 80409 No. of Facilities: 316 (estimated) No. of Industries: 3 No. of Occupations: 7 No. of Employees: 3694 (estimated) No. of Female Employees: 2675 (estimated)

雌三醇安全信息

[ 符号 ]:

GHS08

[ 信号词 ]:
Danger

[ 危害声明 ]:
H351-H360

[ 警示性声明 ]:
P201-P281-P308 + P313

[ 个人防护装备 ]:
Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ 危害码 (欧洲) ]:
T: Toxic;

[ 风险声明 (欧洲) ]:
R60

[ 安全声明 (欧洲) ]:
S53-S22-S36/37/39-S45-S36/37

[ 危险品运输编码 ]:
2811.0

[ WGK德国 ]:
3

[ RTECS号 ]:
KG8225000

[ 危险类别 ]:
6.1

雌三醇合成路线

雌三醇上下游产品

雌三醇上游产品

雌三醇下游产品

雌三醇制备

1.自人胎盘组织、孕妇尿中提取或化学合成制得的雌激素。

2.工业上用雌酚酮为原料生产。

4.制法：

1,2,5（10）-雌三醇-16a，17a-环氧-3,17β-二醇双醋酸酯（3）：于装有搅拌器、温度计、滴液漏斗、回流冷凝器的反应瓶中，加入1,3,5（10），16-雌四烯-3,17-二醇双醋酸酯（2）10g（28mmol），二氯乙烷100mL，无水碳酸钠10g，无水硫酸钠13g，搅拌下滴加过氧乙酸（20%～30%）27g与无水醋酸钠13g配成的溶液，控制反应温度不超过20℃，约20min加完。继续搅拌反应4h。放置过夜。过滤，滤饼用二氯乙烷洗涤。合并滤液和洗涤液，以碳酸氢钠水溶液洗涤，再水洗至中性。无水硫酸钠干燥，减压蒸出二氯乙烷。析出结晶后静置过夜。抽滤，乙醇洗涤，干燥，得1,3,5（10）-雌三醇-16a，17a-环氧-3,17β-二醇双蜡酸酯（3）9.0g，收率86%。此三醇（1）：于装有搅拌器、温度计、滴液漏斗、回流冷凝器的反应瓶中，加入化合物（3）5g，乙醇100mL，搅拌下滴加由硼氢化钾1g，氢氧化钾4g，水20mL配成的溶液，控制反应温度在25～30℃，约0.5h加完，而后继续搅拌反应1h。反应完后用冰醋酸调至弱酸性。减压浓缩至干。加入适量的水，抽滤，滤饼用水洗涤至中性，于80℃干燥，得雌三醇粗品。粗品以20倍的95%的乙醇精制一次，再用乙酸乙酯精制三次，得雌三醇（1），收率50%。

雌三醇文献

Development of a novel magnetic molecularly imprinted polymer coating using porous zeolite imidazolate framework-8 coated magnetic iron oxide as carrier for automated solid phase microextraction of estrogens in fish and pork samples.

J. Chromatogr. A. 1365 , 35-44, (2014)

A high-performance magnetic molecularly imprinted polymer (MIP) coating using zeolite imidazolate framework-8 coated magnetic iron oxide (Fe3O4@ZIF-8) as a carrier was developed for simultaneous autom...

Highly sensitive Fe₃O₄ nanobeads/graphene-based molecularly imprinted electrochemical sensor for 17β-estradiol in water.

Anal. Chim. Acta 884 , 106-13, (2015)

A novel molecularly imprinted electrochemical sensor based on Fe3O4 nanobeads immobilized on graphene (Fe3O4-MIP@RGO) has been developed for detecting 17β-estradiol (17β-E2) in water using reversible ...

Water-compatible magnetic imprinted nanoparticles served as solid-phase extraction sorbents for selective determination of trace 17beta-estradiol in environmental water samples by liquid chromatography.

J. Chromatogr. A. 1396 , 7-16, (2015)

Endocrine disrupting compounds (EDCs) are a potential risk for wildlife and humans for their existence in water. The efficient extraction and clean-up steps are required before detection of low concen...

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雌三醇