1690-62-6

Basic information

• Product Name: 3-HYDROXY-9-METHOXYCOUMESTAN
• Synonyms: 3-HYDROXY-9-METHOXYCOUMESTAN;7-HYDROXY-12-METHOXYCOUMESTAN;9-O-METHYLCOUMESTROL;4'-O-methylcoumesterol;4'-O-Methylcoumestrol;9-Methoxycoumestrol
• CAS NO: 1690-62-6
• Molecular Formula: C16H10O5
• Molecular Weight: 282.25
• Product Categories: Coumarins
• Mol File: 1690-62-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 338-339 °C
• Boiling Point: 519.5°C at 760 mmHg
• Flash Point: 268°C
• Appearance: /
• Density: 1.462g/cm³
• Vapor Pressure: 2.07E-11mmHg at 25°C
• Refractive Index: 1.695
• PKA: 8.27±0.20(Predicted)
• CAS DataBase Reference: 3-HYDROXY-9-METHOXYCOUMESTAN(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDROXY-9-METHOXYCOUMESTAN(1690-62-6)
• EPA Substance Registry System: 3-HYDROXY-9-METHOXYCOUMESTAN(1690-62-6)

Safety Data

• Hazardous Substances Data: 1690-62-6(Hazardous Substances Data)

Usage

General Description

3-Hydroxy-9-methoxycoumestan is a compound belonging to the coumestan class of phytoestrogens, which are naturally occurring plant compounds with estrogenic properties. It is derived from plants such as red clover and has been researched for its potential estrogenic and antiestrogenic activity. 3-HYDROXY-9-METHOXYCOUMESTAN has been studied for its potential use in the treatment of menopausal symptoms, osteoporosis, and breast cancer. Additionally, 3-hydroxy-9-methoxycoumestan has been investigated for its antioxidant and anti-inflammatory properties, as well as its potential role in regulating cholesterol levels. Further research is needed to fully understand the properties and potential applications of this compound.

InChI:InChI=1/C16H10O5/c1-19-9-3-5-10-13(7-9)20-15-11-4-2-8(17)6-12(11)21-16(18)14(10)15/h2-7,17H,1H3

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Relevant articles and documents

3, 9-di-O-substituted coumestrols incorporating basic amine side chains act as novel apoptosis inducers with improved pharmacological selectivity

There is much interest in the use of phytoestrogens such as coumestrol in breast cancer intervention due to their antiestrogenic activity and multiple modes of tumor cell death. However, the clear beneficial effects of naturally occurring estrogen mimetic coumestrol remain controversial due to experimental evidence that it has been shown to stimulate MCF-7 cell proliferation via agonist effect on estrogen receptor at low concentration. Herein, to disconnect the ER interaction and apoptosis-specific mechanism of coumestrol, various 3, 9-di-O-substituted coumestrols (7a-7e) and their furan ring-opened analogs (5a-5e) were synthesized and assessed for antiproliferative properties. Attachment of a dimethylamine-containing side chain to 3-O of coumestrol led to the most promising compound 7e with improved antiproliferative activity (1.7-fold increase) against MCF-7 cells, decreased estrogen activity (>20 times weaker ERα binder) and a novel action to induce apoptosis. Mechanistic studies revealed that 7e is a tubulin polymerization inhibitor, which could arrest cell cycle at G2/M phase and induce apoptosis along with the decrease of mitochondrial membrane potential. In summary, such subtle modifications to the 3, 9-di-hydroxyl groups of coumestrol allow the generation of a novel apoptosis inducer with distinct pharmacological properties, providing an excellent starting point to future development of novel tumor-vascular disrupting agents targeting tubulin.

Copper-catalyzed intramolecular cross dehydrogenative coupling approach to coumestans from 2′-hydroxyl-3-arylcoumarins

A copper-catalyzed intramolecular cross dehydrogenative C-O coupling reaction of 2′-hydroxyl-3-arylcoumarins was developed. This protocol provided a facile and efficient strategy for the construction of natural coumestans and derivatives in moderate to high yields. This transformation exhibited good functional group compatibility and was amenable to substrates with free phenolic hydroxyl groups.

Copper-mediated synthesis of coumestans via C(sp2)-H functionalization: Protective group free route to coumestrol and 4′-O-methylcoumestrol

A simple and efficient two step synthesis of coumestans is described. The key reaction in the synthesis is the use of easily available Cu(OAc)2 for C[sbnd]H functionalization of 3-(2-hydroxyphenyl)coumarin to give coumestan ring system via formal oxidative cyclization. This approach provided a short protective group free route to naturally occurring coumestrol and 4′-O-methylcoumestrol.