36190-95-1

Basic information

• Product Name: 3''-METHOXYOROBOL
• Synonyms: -O-Methylorobol;3'-Methoxy-4',5,7-trihydroxyisoflavone;5,7-Dihydroxy-3-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one;4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)-
• CAS NO: 36190-95-1
• Molecular Formula: C₁₆H₁₂O₆
• Molecular Weight: 300.26288
• Product Categories: Miscellaneous Natural Products
• Mol File: 36190-95-1.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3''-METHOXYOROBOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3''-METHOXYOROBOL(36190-95-1)
• EPA Substance Registry System: 3''-METHOXYOROBOL(36190-95-1)

Safety Data

• Hazardous Substances Data: 36190-95-1(Hazardous Substances Data)

Usage

Uses

3''-Methoxy-4'',5,7-trihydroxyisoflavone is a derivative of Genistein (G350000); a compound that exhibits specific inhibitory activity against tyrosine kinases, including autophosphorylation of epidermal growth factor receptor kinase (IC50 - 2.6uM). Also inhibits other protein kinases through competitive inhibition of ATP. Inhibits tumor cell proliferation and induces tumor cell differentiation. Produces cell-cycle arrest and apoptosis in Jurat T-leukemia cells. However, it prevents anti-CD3 monoclonal antibody-induced thymic apoptosis. Genistein also inhibits topoisomerase II activity in vitro. Genistein has also been shown to inhibit the action of GABA on recombinant GABAA receptors 2.

Upstream product

• 446-72-0 5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on 
• 480-23-9 orobol 
• 446-71-9 homoeriodictyol 

Relevant articles and documents

Microbial hydroxylation and methylation of genistein by Streptomycetes

Streptomyces griseus (ATCC 10137) and Streptomyces catenulae (ATCC 23893) were used to convert genistein-5,7,4'- trihydroxyisoflavone (1)-a major isoflavone found in soybeans, into five metabolites, four of which were previously unknown. These were 5,7,3',4'-tetrahydroxy-8-methylisoflavone (3), 5,7,3',4'-tetrahydroxy-8-methylisoflavanone (4), 5,7,4'- trihydroxy-3'-methoxyisoflavone (5), 5,7,8,3',4'-pentahy- droxyisoflavone (7), and the known compound, 5,7-dihydroxy-3',4'- dimethoxyisoflavone (6). Identities of these metabolites were established by HRFABMS and 1D and 2D NMR correlation spectroscopy.

A Versatile Microbial System for Biosynthesis of Novel Polyphenols with Altered Estrogen Receptor Binding Activity

Isoflavonoids possess enormous potential for human health with potential impact on heart disease and cancer, and some display striking affinities for steroid receptors. Synthesized primarily by legumes, isoflavonoids are present in low and variable abundance within complex mixtures, complicating efforts to assess their clinical potential. To satisfy the need for controlled, efficient, and flexible biosynthesis of isoflavonoids, a three-enzyme system has been constructed in yeast that can convert natural and synthetic flavanones into their corresponding isoflavones in practical quantities. Based on the determination of the substrate requirements of isoflavone synthase, a series of natural and nonnatural isoflavones were prepared and their binding affinities for the human estrogen receptors (ERα and ERβ) were determined. Structure activity relationships are suggested based on changes to binding affinities related to small variations on the isoflavone structure.