53084-11-0

Basic information

• Product Name: 3'-O-METHYLPRATENSEIN
• Synonyms: 5,7-DIHYDROXY-3',4'-DIMETHOXYISOFLAVONE;3'-O-METHYLPRATENSEIN;OROBOL 3',4'-DIMETHYL ETHER
• CAS NO: 53084-11-0
• Molecular Formula: C₁₇H₁₄O₆
• Molecular Weight: 314.29
• Product Categories: Miscellaneous Natural Products
• Mol File: 53084-11-0.mol

Chemical Properties

• Boiling Point: 538.3°Cat760mmHg
• Flash Point: 201.3°C
• Appearance: /
• Density: 1.402g/cm³
• Vapor Pressure: 3.35E-12mmHg at 25°C
• Refractive Index: 1.645
• PKA: 6.44±0.20(Predicted)
• CAS DataBase Reference: 3'-O-METHYLPRATENSEIN(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-O-METHYLPRATENSEIN(53084-11-0)
• EPA Substance Registry System: 3'-O-METHYLPRATENSEIN(53084-11-0)

Safety Data

• Hazardous Substances Data: 53084-11-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C17H14O6/c1-21-13-4-3-9(5-14(13)22-2)11-8-23-15-7-10(18)6-12(19)16(15)17(11)20/h3-8,18-19H,1-2H3

Upstream product

• 122775-35-3 3,4-Dimethoxyphenylboronic acid 
• 31721-94-5 5,7-dihydroxy-chromen-4-one 
• 1236208-89-1 3-(N,N-dimethylamino)-1-(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)prop-2-en-1-one 
• 93-17-4 3,4-dimethoxyphenylacetonitrile 
• 108-73-6 3,5-dihydroxyphenol 
• 53084-06-3 2-(3,4-dimethoxyphenyl)-1-(2,4,6-trihydroxyphenyl)-ethanone 
• 68-12-2 N,N-dimethyl-formamide 
• 446-72-0 5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on 

Downstream Products

• 480-23-9 orobol 

Relevant articles and documents

Identification of ortho catechol-containing isoflavone as a privileged scaffold that directly prevents the aggregation of both amyloid β plaques and tau-mediated neurofibrillary tangles and its in vivo evaluation

In this study, polyhydroxyisoflavones that directly prevent the aggregation of both amyloid β (Aβ) and tau were expediently synthesized via divergent Pd(0)-catalyzed Suzuki-Miyaura coupling and then biologically evaluated. By preliminary structure–activity relationship studies using thioflavin T (ThT) assays, an ortho-catechol containing isoflavone scaffold was proven to be crucial for preventing both Aβ aggregation and tau-mediated neurofibrillary tangle formation. Additional TEM experiment confirmed that ortho-catechol containing isoflavone 4d significantly prevented the aggregation of both Aβ and tau. To investigate the mode of action (MOA) of 4d, which possesses an ortho-catechol moiety, 1H-15N HSQC NMR analysis was thoroughly performed and the result indicated that 4d could directly inhibit both the formation of Aβ42 fibrils and the formation of tau-derived neurofibrils, probably through the catechol-mediated nucleation of tau. Finally, 4d was demonstrated to alleviate cognitive impairment and pathologies related to Alzheimer's disease in a 5XFAD transgenic mouse model.

Cytosine N-isoflavone compound as well as preparation method and application thereof

The invention relates to a cytosine N-isoflavone compound as well as a preparation method and application thereof. The compound has a structural formula as shown in the specification, wherein R1 is selected from one of hydroxyl, alkoxy, amido or halo, R2 is selected from one of hydrogen, alkyl or aryl, and R3 is selected from one or a combination of several of hydroxyl, alkoxy, amido or halo. Compared with the prior art, the cytosine N-isoflavone compound has the characteristic that an isoflavone compound serving as a structural unit is spliced to N on the 12th position of cytosine by using acombined synthesis technology, so that a series of cytosine-isoflavone derivatives are synthesized, and a novel active pharmacological action is exerted.

Synthesis of analogs of natural isoflavonoids containing phloroglucinol

Analogs of the natural isoflavonoids biochanin A and orobol were synthesized. Alkylation involving phenolic hydroxyls and the chromone ring was studied.

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.