CAS 362-05-0|2-Hydroxyestradiol
| Common Name | 2-Hydroxyestradiol | ||
|---|---|---|---|
| CAS Number | 362-05-0 | Molecular Weight | 288.38 |
| Density | 1.2±0.1 g/cm3 | Boiling Point | 481.5±45.0 °C at 760 mmHg |
| Molecular Formula | C18H24O3 | Melting Point | 96-104°C |
| MSDS | ChineseUSA | Flash Point | 227.6±23.3 °C |
| Symbol | GHS08 | Signal Word | Warning |
Names
| Name | 2-hydroxy-17β-estradiol |
|---|---|
| Synonym | More Synonyms |
2-Hydroxyestradiol BiologicalActivity
| 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 >>OthersResearch 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 |
| InChIKey | DILDHNKDVHLEQB-XSSYPUMDSA-N |
| SMILES | CC12CCC3c4cc(O)c(O)cc4CCC3C1CCC2O |
| Storage condition | −20°C |
Toxicological Information
CHEMICAL IDENTIFICATION |
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 |
Articles34
More 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... |
Synonyms
| 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 |
