| Identification | Back Directory | [Name]
2-HYDROXYESTRADIOL | [CAS]
362-05-0 | [Synonyms]
C05301
2-OH-E2α
NSC 61711
2-Oh-estradiol
2-HYDROXYESTRADIOL
2-Hydroxyestradiol-17α
2-Hydroxy-17-estradiol
2-Hydroxy-17β-estradiol
2-Hydroxy-17b-estradiol
(17β)-2-Hydroxyestradiol
2-Hydroxyestradiol-17beta
2-HYDROXY 17-BETA-ESTRADIOL
1,3,5(10)-estratriene-2,3-17β-triol
Estra-1,3,5(10)-triene-2,3,17-triol
Estra-1,3,5(10)-triene-2,3,17b-triol
Estra-1(10),2,4-triene-2,3,17β-triol
1,3,5(10)-ESTRATRIEN-2,3,17-BETA-TRIOL
1,3,5[10]-ESTRATRIENE-2,3-17BETA-TRIOL
2,3,17-Trihydroxyestra-1,3,5(10)-triene
2,3,17b-Trihydroxyestra-1,3,5(10)-triene
(17)-Estra-1,3,5(10)-triene-2,3,17-triol
estra-1,3,5(10)-triene-2,3,17-beta-triol
(17b)-Estra-1,3,5(10)-triene-2,3,17-triol
2,3,17BETA-TRIHYDROXY-1,3,5[10]-ESTRATRIENE
Estra-1,3,5(10)-triene-2,3,17-triol, (17β)-
1,3,5(10)-Estratriene-2,3-17β-triol, Estra-1,3,5(10)-triene-2,3,17-triol | [Molecular Formula]
C18H24O3 | [MDL Number]
MFCD00010490 | [MOL File]
362-05-0.mol | [Molecular Weight]
288.38 |
| Chemical Properties | Back Directory | [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 ]
neat |
| Hazard Information | Back Directory | [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). |
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