362-08-3

Basic information

• Product Name: 2-METHOXYESTRONE
• Synonyms: 2,3-DIHYDROXY-1,3,5[10]-ESTRATRIEN-17-ONE 2-METHYL ETHER;2-METHOXYESTRONE;2-HYDROXYESTRONE 2-METHYL ETHER;1,3,5(10)-ESTRATRIEN-2,3-DIOL-17-ONE 2-METHYL ETHER;3-HYDROXY-2-METHOXY-1,3,5[10]-ESTRATRIEN-17-ONE;3-hydroxy-2-methoxyestra-1,3,5(10)-trien-17-one;3-hydroxy-2-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one;2,3-Dihydroxy-1,3,5(10)-estratrien-17-one 2-methyl ether, 2-Hydroxyestrone 2-methyl ether, 3-Hydroxy-2-methoxy-1,3,5(10)-estratrien-17-one
• CAS NO: 362-08-3
• Molecular Formula: C19H24O3
• Molecular Weight: 300.39
• EINECS: 206-645-6
• Product Categories: Isolabel
• Mol File: 362-08-3.mol
• Article Data: 29

Chemical Properties

• Melting Point: 187.0-189.5 °C
• Boiling Point: 463.5°Cat760mmHg
• Flash Point: 165.9°C
• Appearance: /
• Density: 1.172g/cm³
• Vapor Pressure: 3.27E-09mmHg at 25°C
• Refractive Index: 1.575
• Storage Temp.: 2-8°C
• PKA: 10.27±0.40(Predicted)
• CAS DataBase Reference: 2-METHOXYESTRONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHOXYESTRONE(362-08-3)
• EPA Substance Registry System: 2-METHOXYESTRONE(362-08-3)

Safety Data

• Hazard Codes: Xn,N
• Statements: 40-50/53
• Safety Statements: 22-36-61-60
• RIDADR: UN3077 9/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 362-08-3(Hazardous Substances Data)

Usage

Description

2-Methoxyestrone, also known as 2-MEO, is a 17-oxo steroid that is estrone in which the hydrogen at position 2 is substituted by a methoxy group. It is an endogenous estrogen metabolite derived from the metabolism of estrogen in the body. 2-METHOXYESTRONE plays a significant role in various physiological processes and has been linked to the development and progression of certain health conditions.

Uses

Used in Medical Applications:
2-Methoxyestrone is used as a breast cancer biomarker for assessing the risk factors for the development of breast cancer. Its detection can help in early diagnosis and timely intervention, potentially improving the prognosis and treatment outcomes for patients.
Used in Research and Development:
As an endogenous estrogen metabolite, 2-Methoxyestrone is used in research to study the effects of estrogen on various physiological processes and its role in the development of hormone-related health conditions. This knowledge can contribute to the development of targeted therapies and personalized treatment strategies for patients with hormone-sensitive conditions.
Used in Drug Development:
Understanding the role of 2-Methoxyestrone in hormone-related conditions can aid in the development of new drugs or therapies that target estrogen metabolism or its effects on the body. This can lead to the creation of more effective treatments for conditions such as breast cancer and other hormone-sensitive diseases.

InChI:InChI=1/C19H24O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-16(20)17(22-2)10-14(11)12/h9-10,12-13,15,20H,3-8H2,1-2H3/t12-,13+,15-,19-/m0/s1

Upstream product

• 1728-46-7 2-tert-butylcyclohexanone 
• 83274-89-9 (13S,17S)-17-hydroxy-2-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl acetate 
• 26357-05-1 Acetic acid (8R,9S,13S,14S)-3-benzyloxy-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-2-yl ester 
• 26357-04-0 2-acetyl-3-benzyloxyestra-1,3,5⁽¹⁰⁾-trien-17-one 
• 26357-06-2 (8R,9S,13S,14S)-3-Benzyloxy-2-hydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one 
• 1624-62-0 estrone 3-methyl ether 
• 26357-03-9 2-acetyl-3-methoxy-estra-1,3,5⁽¹⁰⁾-trien-17-one 
• 26357-02-8 2-acetyl-3-hydroxyestra-1,3,5⁽¹⁰⁾-trien-17-one 
• 901-93-9 estrone acetate 
• 217792-90-0 (8R,9S,13S,14S,17S)-2-methoxy-3,17-bis(methoxymethoxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene 
• 217792-89-7 (8R,9S,13S,14S,17S)-3,17-bis(methoxymethoxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-2-ol 
• 113680-55-0 (8R,9S,13S,14S,17S)-3,17-bis(methoxymethoxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene 
• 53-16-7 Estrone 
• 700369-39-7 2-formyl-3-O-methoxymethyl-17,17-ethylenedioxyestrone 

Downstream Products

• 1620910-45-3 2-methoxy-17-(1-(3,4,5-trimethoxybenzyl)-1H-1,2,3-triazol-4-yl)estradiol 
• 1620910-43-1 2-methoxy-17-(1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)estradiol 
• 1620910-41-9 2-methoxy-17-(1-(4-(trifluoromethoxyl)phenyl)-1H-1,2,3-triazol-4-yl)estradiol 
• 1620910-39-5 2-methoxy-17-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,3-triazol-4-yl)estradiol 
• 1620910-37-3 2-methoxy-17-(1-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazol-4-yl)estradiol 
• 1620910-35-1 2-methoxy-17-(1-(4-methoxyphenyl)-1H-1,2,3-triazol-4-yl)estradiol 
• 1620910-33-9 2-methoxy-17-(1-(4-bromophenyl)-1H-1,2,3-triazol-4-yl)estradiol 
• 1620910-30-6 2-methoxy-17-(1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)estradiol 

Relevant articles and documents

A-ring-substituted estrogen-3-O-sulfamates: Potent multitargeted anticancer agents

Efficient and flexible syntheses of 2-substituted estrone, estradiol and their 3-O-sulfamate (EMATE) derivatives have been developed using directed ortho-lithiation methodology. 2-Substituted EMATEs display a similar antiproliferative activity profile to the corresponding estradiols against a range of human cancer cell lines. 2-Methoxy (3, 4), 2-methylsulfanyl (20, 21) and 2-ethyl EMATEs (32, 33) proved the most active compounds with 2-ethylestradiol-3-O-sulfamate (33), displaying a mean activity over the NCI 55 cell line panel 80-fold greater than the established anticancer agent 2-methoxyestradiol (2). 2-Ethylestradiol-3-O-sulfamate (33) was also an effective inhibitor of angiogenesis using three in vitro markers, and various 2-substituted EMATEs also proved to be inhibitors of steroid sulfatase (STS), a therapeutic target for the treatment of hormone-dependent breast cancer. The potential of this novel class of multimechanism anticancer agents was confirmed in vivo with good activity observed in the NCI hollow fiber assay and in a MDA-MB-435 xenograft mouse model.

Discovery of chalcone-modified estradiol analogs as antitumour agents that Inhibit tumour angiogenesis and epithelial to mesenchymal transition

Angiogenesis plays an essential role in tumourigenesis and tumour progression, and anti-angiogenesis therapies have shown promising antitumour effects in solid tumours. 2-Methoxyestradiol (2ME2), an endogenous metabolite of estradiol, has been regarded as a potential antitumour agent mainly targeting angiogenesis. Here we synthesized a novel series of chalcones based on 2-methoxyestradiol and evaluated their potential activities against tumours. Compound 11e was demonstrated to have potent antiangiogenic activity. Further studies showed that 11e suppressed tumour growth in human breast cancer (MCF-7)xenograft models without obvious side effects. Evaluation of the mechanism revealed that 11e targeted the epithelial to mesenchymal transition (EMT)process in MCF-7 cells and inhibited HUVEC migration and then contributed to hindrance of angiogenesis. Thus, 11e may be a promising antitumour agent with excellent efficacy and low toxicity.

Synthesis and antimitotic activity of novel 2-methoxyestradiol analogs. Part III

The syntheses and antimitotic activity of several novel analogs of 2-methoxyestradiol are described. Structural modifications include ring-D homologation, aromatization of the six-membered ring-D to a chrysine type molecule, and introduction of unsaturation in five-membered ring-D along with substitution of alkyl and ethynyl groups for the 17β-hydroxy function. Of nine analogs synthesized, five have demonstrated superior antiproliferative activities compared to 2-methoxyestradiol.

For female steroid nucleus to 2 bit or 16 substituted chalcone derivative and its preparation and use

The invention belongs to the field of medicinal chemicals, and relates to a 2/16-site-substituted chalcone derivative taking estrogen as a mother nucleus and a preparation method and application of the derivative. The preparation method comprises the following step: combining chalcone structural fragments on an estrogen body in parallel, thereby keeping or improving the activity of anti-tumor cells and inhibiting activity of tumor cell angiogenesis. The structural formula of the 2/16-site-substituted chalcone derivative is as shown in the specification. The in-vitro anti-tumor cell proliferation activity test and the chick embryo allantois test show that the derivative has certain anti-tumor cell proliferation activity and inhibiting activity of tumor cell angiogenesis; and the dose-effect relationship study shows that the tumor cell inhibition function of the derivative is prior to that of 2-methoxy estradiol with broad-spectrum anti-tumor activity, and moreover the half-life period can be prolonged.

Preparation and Catalytic Property of Multi-walled Carbon Nanotubes Supported Keggin-Typed Tungstosilicic Acid for the Baeyer-Villiger Oxidation of Ketones

Multi-walled carbon nanotubes (MWCNTs) supported HSiW/MWCNTs was successfully prepared and characterized by Fourier transform infrared spectoscopy, X-ray powder diffraction, transmission electron microscopy and N2 adsorption-desorption test. Its catalytic performance for the catalytic Baeyer-Villiger oxidation of cyclic ketones with 30 % H2O2 as oxidants was investigated. It was found that HSiW/MWCNTs was very efficient to transform of some cycloketones to the corresponding lactones with high conversions as well as selectivities. Factors affecting the oxidations and the reusability of the catalyst were also investigated. It was found that the catalyst can be reused seven times in the catalytic oxidation reaction of cyclopentanone without obviously catalytic activity losing in the oxidation. Graphical Abstract: A supported solid acid of HSiW/MWCNTs was used as efficient catalyst for the Baeyer-Villiger oxidation of ketones. High cyclopentanone conversion (98 %) and ε- valerolactone selectivity (99 %) were obtained. The catalyst can be reused at least seven runs in the oxidation of cyclopentanone.