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

Safety Information

Hazard Codes 

Xn

Risk Statements 

40

Safety Statements 

22-36

WGK Germany 

3

RTECS 

KG7675000

MSDS

• Language:English Provider:SigmaAldrich

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(362-05-0)Related Product Information

• Estriol
• 2-Hydroxyestradiol 2-Methyl Ether
• 4-hydroxyestradiol approx. 90% (hplc),4-HYDROXYESTRADIOL,4-hydroxyestradiol-17bet
• 16BETA-HYDROXYESTRADIOL,16b-Hydroxyestradiol
• β-Estradiol
• 1,3,5(10)-ESTRATRIEN-2,3-DIOL-17-ONE 2-METHYL ETHER 3-ACETATE 17-ETHYLENEKETAL
• 1,3,5(10)-ESTRATRIEN-2,3,16ALPHA,17BETA-TETROL 2-METHYL ETHER
• 2-HYDROXYESTRIOL
• 2-METHOXYESTRADIOL [6,7-3H]
• 2-METHOXY-17BETA-ESTRADIOL-1,4,16,16,17-D5
• 2-Hydroxyestradiol-1,4,16,16,17-d5
• 2-HYDROXY-3,17BETA-O-BIS(METHOXYMETHYL)ESTRADIOL
• 1,3,5(10)-ESTRATRIEN-2,3-DIOL-17-ONE 3-METHYL ETHER 17-ETHYLENEKETAL
• 2-HYDROXYESTRADIOL
• 17a-Ethynyl-2-hydroxyestradiol 3-Methyl Ether
• 6A-hydroxyestradiol,6ALPHA-HYDROXYESTRADIOL,6α-Hydroxyestradiol
• 15α-Hydroxyestradiol,15ALPHA-HYDROXYESTRADIOL
• 2-Hydroxyestradiol 2-Methyl-d3 Ether