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
• Article Data: 4

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

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

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.

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.