530-22-3

Basic information

• Product Name: 5-(3-Hydroxypropyl)-7-methoxy-2-(3,4-methylenedioxyphenyl)benzofuran
• Synonyms: 5-(3-Hydroxypropyl)-7-methoxy-2-(3,4-methylenedioxyphenyl)benzofuran;Egonol;2-(1,3-Benzodioxol-5-yl)-7-methoxy-5-benzofuran-(1-propanol);3-[2-(1,3-Benzodioxol-5-yl)-7-methoxybenzofuran-5-yl]-1-propanol
• CAS NO: 530-22-3
• Molecular Formula: C₁₉H₁₈O₅
• Molecular Weight: 326.34322
• Mol File: 530-22-3.mol
• Article Data: 12

Chemical Properties

• Melting Point: 118°C
• Boiling Point: 424.39°C (rough estimate)
• Flash Point: 265.6°C
• Appearance: /
• Density: 1.2068 (rough estimate)
• Vapor Pressure: 1.88E-11mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• CAS DataBase Reference: 5-(3-Hydroxypropyl)-7-methoxy-2-(3,4-methylenedioxyphenyl)benzofuran(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(3-Hydroxypropyl)-7-methoxy-2-(3,4-methylenedioxyphenyl)benzofuran(530-22-3)
• EPA Substance Registry System: 5-(3-Hydroxypropyl)-7-methoxy-2-(3,4-methylenedioxyphenyl)benzofuran(530-22-3)

Safety Data

• Hazardous Substances Data: 530-22-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C19H18O5/c1-21-18-8-12(3-2-6-20)7-14-10-16(24-19(14)18)13-4-5-15-17(9-13)23-11-22-15/h4-5,7-10,20H,2-3,6,11H2,1H3

Upstream product

• 164414-67-9 7-methoxy-2-(3,4-methylenedioxyphenyl)-5-(3-tetrahydropyranyloxypropyl)benzofuran 
• 23343-24-0 9'-nor-7,8-dehydro-Isolicarin B 
• 107365-53-7 benzo[1,3]dioxol-5-yl-chloro-acetic acid ethyl ester 
• 25054-53-9 3,4-(methylenedioxy)benzoyl chloride 
• 110057-59-5 4-allyl-2-(hydroxymethyl)-6-methoxyphenol 
• 85614-43-3 2-hydroxy-3-methoxy-5-(2-propeny)benzoic acid, methyl ester 
• 22934-51-6 5-allyl-2-hydroxy-3-methoxybenzaldehyde 
• 23343-06-8 2-allyloxy-3-methoxy-benzaldehyde 
• 210229-45-1 5-allyl-2-hydroxy-3-methoxybenzyl chloride 
• 20037-38-1 4-bromo-2-formyl-6-methoxyphenylacetic acid 
• 164414-62-4 5-bromo-7-methoxybenzofuran 
• 164414-63-5 7-methoxy-5-(3-tetrahydropyranyloxopropyl)benzofuran 
• 15434-00-1 3-(2-(benzo[d][1,3]dioxol-5-yl)-7-methoxybenzo[b]furan-5-yl)propyl acetate 
• 1336884-95-7 egonol-9(Z),12(Z)-linoleate 

Relevant articles and documents

NEW BENZOFURANS RELATED TO EGONOL FROM IMMATURE SEEDS OF STYRAX OBASSIA

Three new benzofurans have been isolated from immature seeds of Styrax obassia.Their structures have been established as 5--7-methoxy-2-(3',4'-methylene dioxyphenyl)benzofuran (3), 5--2-(3',4'-methylenedioxy-phenyl)benzofuran (5), and 5--7-methoxy-2-(3',4'-methylenedioxyphenyl)benzofuran (6), respectively, based on their chemical and spectroscopic properties and enzymatic reaction.Egonol acetate (2) were also identified.Key Word Index - Styrax obassia; styrocaceae; egonol; benzofuran; glucoside; 2-methylbutanoate.

Synthesis and Cytotoxicity Studies of Bioactive Benzofurans from Lavandula agustifolia and Modified Synthesis of Ailanthoidol, Homoegonol, and Egonol

2-Aryl/alkylbenzofurans, which constitute an important subclass of naturally occurring lignans and neolignans, have attracted extensive synthetic efforts due to their useful biological activities and significant pharmacological potential. Herein, we report a general and efficient approach to divergent 2-arylbenzofurans through a one-pot synthesis of versatile 2-bromobenzofurans as key intermediates. Using this approach, the first total synthesis of a series of trisubstituted and tetrasubstituted benzofurans bearing the hydroxyethyl unit, including the natural compounds isolated from Lavandula agustifolia (1-3) and their non-natural derivatives (4-8), was accomplished. We also report a modified synthesis of ailanthoidol, homoegonol, and egonol that enables the divergent synthesis of their derivatives for future exploration. Among these, the representative phenolic natural compound 2 and its derivatives 7 and 5 induced apoptotic cell death related poly(ADP-ribose) polymerase (PARP) cleavage in MCF74, A549, PC3, HepG2, and Hep3B cancer cell lines. Additionally, the tumor suppressor protein p53 was also induced in p53 wild type cancer cells.

An alternate method for the synthesis of 2-aryl/alkyl-5-bromo-7-methoxy benzofurans; application to the synthesis of Egonol, Homoegonol, and analogs via Heck reaction

We herein report the general, versatile, and convenient method for the synthesis of 2-arly/alkyl-5-bromo-7-methoxy benzofurans from easily available o-Vanillin in five steps. These benzofurans was successfully converted into biological active natural products Egonol, Homoegonol, and analogous on applying Heck reaction using ethyl/methyl acrylate in the presence of palladium catalyst.