|
|
| | 2-Hydroxyestradiol Basic information |
| Product Name: | 2-Hydroxyestradiol | | Synonyms: | estra-1,3,5(10)-triene-2,3,17-beta-triol;1,3,5(10)-Estratriene-2,3-17β-triol, Estra-1,3,5(10)-triene-2,3,17-triol;2-Hydroxyestradiol-17α;2-OH-E2α;(17β)-2-Hydroxyestradiol;Estra-1(10),2,4-triene-2,3,17β-triol;2-HYDROXY 17-BETA-ESTRADIOL;2,3,17BETA-TRIHYDROXY-1,3,5[10]-ESTRATRIENE | | CAS: | 362-05-0 | | MF: | C18H24O3 | | MW: | 288.38 | | EINECS: | | | Product Categories: | Metabolites & Impurities;Steroids | | Mol File: | 362-05-0.mol |  |
| | 2-Hydroxyestradiol Chemical Properties |
| Melting point | 96-104°C | | Boiling point | 370.61°C (rough estimate) | | density | 1.1285 (rough estimate) | | refractive index | 1.5000 (estimate) | | storage temp. | −20°C | | solubility | ≤20mg/ml in ethanol;20mg/ml in DMSO;20mg/ml in dimethyl formamide | | form | Solid | | color | White to light yellow | | biological source | synthetic (organic) | | InChI | 1S/C18H24O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,17,19-21H,2-7H2,1H3/t11-,12+,14-,17-,18-/m0/s1 | | InChIKey | DILDHNKDVHLEQB-XSSYPUMDSA-N | | SMILES | C[C@]12CC[C@H]3[C@@H](CCc4cc(O)c(O)cc34)[C@@H]1CC[C@@H]2O |
| Hazard Codes | Xn | | Risk Statements | 40 | | Safety Statements | 22-36 | | WGK Germany | 3 | | RTECS | KG7675000 | | Storage Class | 13 - Non Combustible Solids | | Hazard Classifications | Carc. 2 |
| | 2-Hydroxyestradiol Usage And Synthesis |
| Chemical Properties | Pale Yellow Solid | | Uses | A metabolite of Estradiol | | Definition | ChEBI: A 2-hydroxy steroid that consists of 17beta-estradiol having an additional hydroxy group at position 2. | | Biological Activity | 2-hydroxyestradiol is an angiogenesis inhibitor via the hif-1a pathway.hif-1a, a basic helix-loop-helix pas domain containing protein, is reported as the master transcriptional regulator of cellular and developmental response to hypoxia. | | in vitro | in vitro evidences suggested that most of the cellular effects of 2-hydroxyestradiol were mediated by 2-methoxyestradiol, a metabolite of 2-hydroxyestradiol as an anti-cancer agent acting as an angiogenesis inhibitor via the hif-1a pathway. inhibition of catechol-o-methyltransferase (comt), the enzyme methylating 2-hydroxyestradiol to 2-methoxyestradiol, blocked the ability of 2-hydroxyestradiol to inhibit growth of vascular smooth muscle cells, cardiac fibroblasts, as well as renal mesangial cells. moreover, 2-hydroxyestradiol could inhibit vascular smooth muscle cell growth in cells obtained from wild-type mice but not in cells cultured from comt knockout mice. in contrast to 2ohe, treatment of vascular smooth muscle cells with 2-methoxyestradiol inhibited serum-induced growth of cells from both wild-type and comtknockout mice [1]. | | in vivo | animal study showed that after administration of 2-hydroxyestradiol, plasma levels of 2-hydroxyestradiol declined extremely rapidly. concomitant with the disappearance of 2-hydroxyestradiol, 2-methoxyestradiol occurred and then declined. after administration of 2-methoxyestradiol, plasma levels of 2meoe declined with a plasma cl of 50 ml min(-1) kg(-1). we could not detect 2-hydroxyestradiol in plasma from rats receiving 2-methoxyestradiol. thus, the authors conclude that the conversion of 2-hydroxyestradiol to 2-methoxyestradiol was so efficient, and the administration of 2-hydroxyestradiol is bioequivalent to administration of 2-methoxyestradiol itself [1]. | | references | [1] zacharia, l. c.,piché, c.a.,fielding, r.m., et al. 2-hydroxyestradiol is a prodrug of 2-methoxyestradiol. journal of pharmacology and experimental therapeutics 309(3), 1093-1097 (2004). |
| | 2-Hydroxyestradiol Preparation Products And Raw materials |
|