ChemicalBook > CAS DataBase List > 2-HYDROXYESTRADIOL

2-HYDROXYESTRADIOL

CAS No.362-05-0
Chemical Name:2-HYDROXYESTRADIOL
CBNumber:CB7767256
Molecular Formula:C18H24O3
Formula Weight:288.38
MOL File:362-05-0.mol

2-HYDROXYESTRADIOL Property

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)
EWG's Food Scores 1
FDA UNII AYU2L67YUU
UNSPSC Code 12352200
NACRES NA.77

Safety

Hazard Codes :Xn
Risk Statements :40
Safety Statements :22-36
WGK Germany :3
RTECS :KG7675000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H351
Precautionary statements P281

2-HYDROXYESTRADIOL Chemical Properties,Usage,Production

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).