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Usage

Uses

Used in Pharmaceutical Industry:
Chalcone is used as a pharmaceutical agent for its potential antioxidant, anti-inflammatory, and antimicrobial properties. Its ability to modulate various biological pathways and exhibit synergistic effects with other drugs makes it a promising candidate for the development of therapeutic agents.
Used in Cosmetic Industry:
Chalcone is used as an active ingredient in cosmetic products for its antioxidant and anti-inflammatory properties. It helps protect the skin from oxidative stress and inflammation, promoting a healthy and youthful appearance.
Used in Food Industry:
Chalcone is used as a natural food additive for its antimicrobial properties. It helps preserve the freshness and quality of food products by inhibiting the growth of harmful microorganisms.
Used in Nutraceutical Industry:
Chalcone is used as a nutraceutical ingredient for its potential health benefits. It can be incorporated into dietary supplements and functional foods to support overall health and well-being.
Used in Agricultural Industry:
Chalcone is used as a natural pesticide in agriculture for its antimicrobial properties. It helps protect crops from diseases and pests, promoting healthy plant growth and increased yield.

Upstream product

• 5034-74-2 5-bromo-3-methoxysalicylaldehyde 
• 1233720-56-3 2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxyprop-1-ynyl)-7-methoxybenzofuran 
• 56897-51-9 5-bromo-7-methoxy-2-nitrobenzofuran 
• 213970-71-9 2-(p-hydroxy-m-methoxyphenyl)-7-methoxy-5-(carbethoxy-1-propen-1-yl)benzo[b]furan 
• 269410-22-2 4-hydroxy-3-methoxyphenylboronic acid pinacol ester 
• 10543-12-1 4-acetoxy-3-methoxybenzoic acid 
• 110057-59-5 4-allyl-2-(hydroxymethyl)-6-methoxyphenol 
• 56681-66-4 3-methoxy-4-acetoxybenzoyl chloride 
• 121-34-6 3-methoxy-4-hydroxybenzoic acid 
• 97-53-0 4-allylguaiacol 
• 947232-07-7 2-(2,2-dibromovinyl)-6-methoxyphenol 
• 7359-14-0 2-hydroxy-5-iodo-3-methoxybenzaldehyde 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 

Relevant academic research and scientific papers

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.

A Convergent Total Synthesis of the Biologically Active Benzofurans Ailanthoidol, Egonol and Homoegonol from Biomass-Derived Eugenol

An efficient, general synthetic protocol for the synthesis of the biologically active benzofurans ailanthoidol, egonol and homoegonol was developed. The key starting material, eugenol, is a naturally occurring and abundant precursor. The protocol, involving sequential acylation and intramolecular Wittig reaction, provides a convenient method for building the benzofuran moiety in good yield.

Rapid Access to Benzofuran-Based Natural Products through a Concise Synthetic Strategy

A concise strategy is described for the synthesis of ailanthoidol (1), egonol (2), homoegonol (3), demethoxyegonol (4), demethoxyhomoegonol (5), and stemofuran A (6). This approach involves a Pd-catalysed domino cyclization/coupling process using triarylbismuth reagents for the generation of the benzofuran core. Subsequent structural modifications then give the final targets. The high yielding synthesis of the recently isolated natural products egonol-9(Z)-12(Z)-linoleate (2a), 7-demethoxyegonol-9(Z)-12(Z)-linoleate (4a), and 7-demethoxy-egonol-9(Z)-oleate (4b) are also reported.

Total synthesis of ailanthoidol, egonol, and related analogues

Efficient and general synthetic protocols were developed for the total synthesis of ailanthoidol, egonol, and some related analogues. The key transformations describe here involve a two-step construction of the benzofuran and a Sonogashira coupling, and proved to be convenient and effective, starting from readily available reagents.

Facile preparation of 2-arylbenzo[b]furan molecules and their anti-inflammatory effects

An efficient and practical preparation of 2-arylbenzo[b]furan molecules including natural egonol, XH-14, ailanthoidol, and unnatural derivatives is demonstrated using Sonogashira coupling, iodine induced cyclization and Wittig reaction. Anti-inflammatory effects of the prepared benzo[b]furans were examined in lipopolysaccharide (LPS)-stimulated RAW 264-7 macrophages. The results showed that ailanthoidol, XH-14 and three other unnatural derivatives (9-10, 13) inhibited significantly the production of inflammatory mediator nitric oxide without showing cytotoxicity.

An expeditious and convergent synthesis of ailanthoidol

An expeditious and concise method has been described for the synthesis of ailanthoidol through convergent route starting from vanillin. The protocol involving intramolecular Wittig as a key reaction afforded ailanthoidol in overall high yield.

Total synthesis of ailanthoidol and precursor XH14 by stille coupling

Ailanthoidol 1, which can be isolated from Chinese herbal medicine, is achieved in which the longest linear sequence is only six steps in 48% overall yield from commercially available 5-bromo-2-hydroxy-3-methoxybenzaldehyde. The key transformations in the

A novel strategy for the synthesis of benzofuran skeleton neolignans: Application to ailanthoidol, XH-14, and obovaten

A convenient and general approach to the synthesis of the benzofuran skeleton compounds ailanthoidol, XH-14, and obovaten was developed. Starting from vanillin, a series of reactions afforded 7 in 71% yield. Treatment of 7 with n-BuLi followed by addition of substituted benzaldehydes resulted in the formation of carbinols 11 and 31. The substituted benzophenones obtained from oxidation of 11 and 31 were treated with trimethylsilyldiazomethane lithium salt to give diphenylacetylenes 15 and 33, respectively. 15 and 33 were then cyclized in the presence of either mercury acetate in acetic acid or bromine in chloroform to give 3-chloromercurio- or 3-bromobenzofuran, respectively. The 3-chloromercurio intermediates could be reduced to proton or derivatized to ester or bromide, leading to the synthesis of ailanthoidol, XH-14, and obovaten, respectively. In addition, necleophilic substitution was used to introduce a formyl or methyl group into the 3-bromobenzofuran derivatives, providing an alternative pathway to XH-14 and obovaten. The final elongation and deprotection reaction furnished the desired ailanthoidol, XH-14, and obovaten in yields of 30, 15, and 11%, respectively.

A convenient synthesis of naturally occurring benzofuran ailanthoidol

A convenient method for the synthesis of ailanthoidol starting from vanillin is provided using trimethylsilyldiazomethane lithium salt to generate a diphenylacetylene and subsequent oxymercuration cyclization of the resulting alkyne with mercury acetate in acetic acid as key steps.

A new approach to 2-aryl-7-alkoxy-benzofurans: Synthesis of ailanthoidol, a natural neolignan

A general method of synthesis of 2-aryl-7-alkoxy-benzofurans is described using a benzoannulation reaction as key step. The usefulness of this approach is shown in the new synthesis of ailanthoidol, a benzofuranoid neolignan isolated from the tree Zanthox