4737-27-3

Usage

Uses

Used in Pharmaceutical Industry:
Isoflavone is used as a pharmaceutical agent for its potential health benefits, including its antioxidant, anti-inflammatory, and estrogenic properties. It has been studied for its potential role in managing menopausal symptoms, improving bone health, and reducing the risk of certain types of cancer, such as breast and prostate cancer.
Used in Functional Foods and Supplements:
Isoflavone is used as an ingredient in functional foods and dietary supplements due to its potential health-promoting effects. It is often marketed as a natural alternative to hormone replacement therapy for menopausal women and is included in products aimed at promoting cardiovascular health and supporting bone density.
Used in Cosmetics Industry:
Isoflavone is used as an active ingredient in cosmetics for its potential skin health benefits. It may be included in skincare products for its antioxidant properties, which can help protect the skin from environmental damage and promote a more youthful appearance.
Used in Agriculture:
Isoflavone can be used in agriculture as a natural plant growth promoter or as a component of biopesticides. Its presence in certain plants can also contribute to the overall nutritional value of crops, making them more beneficial for human consumption.

Synthesis Reference(s)

Tetrahedron Letters, 14, p. 1659, 1973 DOI: 10.1016/S0040-4039(01)96021-6

InChI:InChI=1/C15H12O2/c16-15-12-8-4-5-9-14(12)17-10-13(15)11-6-2-1-3-7-11/h1-9,13H,10H2

Upstream product

• 108-86-1 bromobenzene 
• 42327-53-7 chrom-3-en-4-ol acetate 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 507233-69-4 triphenyl bismuth ⁽²⁺⁾; dichloride 
• 47252-14-2 triphenylbismuth carbonate 
• 36838-59-2 N-styrylmorpholine 
• 119841-74-6 salicylhydroxamoyl chloride 
• 1786-05-6 4-hydroxy-3-phenylcoumarin 
• 574-12-9 isoflavone 
• 108-90-7 chlorobenzene 
• 55454-07-4 4-trimethylsilyloxy-1,2-benzopyran 
• 144930-50-7 mesityl(phenyl)iodonium triflouromethanesulfonate 
• 102-96-5 (2-nitroethenyl)benzene 
• 90-02-8 salicylaldehyde 

Downstream Products

• 1481-96-5 trans-2,3-dihydro-3-phenyl-4H-benzopyran-4-ol 
• 1481-96-5 cis-2,3-dihydro-3-phenyl-4H-benzopyran-4-ol 
• 1186060-80-9 3-(2-methylallyl)-3-phenylchroman-4-one 
• 1186060-62-7 (R)-3-(2-methylallyl)-3-phenylchroman-4-one 
• 1186060-68-3 (R)-3-phenyl-3-(3-(trimethylsilyl)prop-2-ynyl)chroman-4-one 
• 1186060-65-0 (R)-3-benzyl-3-phenylchroman-4-one 
• 1186060-48-9 (R)-3-allyl-3-phenylchroman-4-one 
• 1186060-66-1 (R)-3-(4-bromobenzyl)-3-phenylchroman-4-one 
• 1186060-67-2 (R)-3-(4-fluorobenzyl)-3-phenylchroman-4-one 

Relevant academic research and scientific papers

Enantioselective α-Arylation of Ketones via a Novel Cu(I)-Bis(phosphine) Dioxide Catalytic System

A novel catalytic system based on copper(I) and chiral bis(phosphine) dioxides is described. This allows the arylation of silyl enol ethers to access enolizable α-arylated ketones in good yields and enantiomeric excess up to 95%. Noncyclic ketones are amenable substrates with this method, which complements other approaches based on palladium catalysis. Optimization of the ligand structure is accomplished via rational design driven by correlation analysis. Preliminary mechanistic hypotheses are also evaluated in order to identify the role of chiral bis(phosphine) dioxides.

Blue Light Promoted Difluoroalkylation of Aryl Ketones: Synthesis of Quaternary Alkyl Difluorides and Tetrasubstituted Monofluoroalkenes

A facile and cost-effective method for the preparation of fluoroalkylated compounds has been described by the direct photoexcitation of halofluoroalkanes with blue light absorptivity, enabling the difluoroalkylation of aryl ketones. The methodology has provided an efficient, mild, and catalyst-free synthetic method for quaternary difluoroalkylated arenes and tetrasubstituted monofluoroalkenes.

NHC-Catalyzed Dual Stetter Reaction: A Mild Cascade Annulation for the Syntheses of Naphthoquinones, Isoflavanones, and Sugar-Based Chiral Analogues

The N-heterocycle carbene (NHC)-catalyzed dual Stetter cascade reaction is discovered through coupling of β-nitrostyrene with phthalaldehyde under mild conditions to furnish valuable aryl-naphthoquinones. The generality of the new reaction is validated through the development of a C-C and O-C bond forming Stetter cascade reaction using salicylaldehydes to obtain functionalized dihydroisoflavanones. The mild NHC organocatalysis is successfully employed for the construction of optically pure sugar-based naphthoquinones and dihydroisoflavanones. Herein, NHC is found as a unique and powerful organocatalyst to construct homoatomic C-C cross-coupling, heteroatomic O-C bond formation, and cascade cyclization utilizing NO2 as a leaving group at ambient temperature. A mechanistic pathway of the new metal-free catalysis is predicted on the basis of our ESI-MS study of the ongoing reaction and literature.

Comprehensive evaluation of antioxidant effects of Japanese Kampo medicines led to identification of Tsudosan formulation as a potent antioxidant agent

Oxidative stress due to the overproduction of reactive oxygen species plays an important role in the pathogenesis of various diseases. In the present study, we comprehensively evaluated the antioxidant activities of 147 oral formulations of Japanese traditional herbal medicines (Kampo medicines), representing the entire panel of oral Kampo medicines listed in the Japanese National Health Insurance Drug List, using in vitro radical scavenging assays, including the 2,2-diphenyl-1-picrylhydrazyl free radical scavenging activity assay, the superoxide anion scavenging activity assay, and the oxygen radical absorption capacity assay. Three of the formulations tested, namely, Tsudosan, Daisaikoto, and Masiningan, showed the most potent in vitro antioxidant activities and were selected for further investigation of their intracellular and in vivo antioxidant effects. The results of the 2′,7′-dichlorodihydrofluorescin diacetate assay demonstrated that all three Kampo medicines significantly inhibited hydrogen peroxide-induced oxidative stress in human hepatocellular liver carcinoma HepG2 cells. In addition, Tsudosan significantly increased the serum biological antioxidant potential values when orally administrated to mice, indicating that it also had in vivo antioxidant activity. The potent antioxidant activity of Tsudosan may be one of the mechanisms closely correlated to its clinical usage against blood stasis.

Desulfonylative Methenylation of β-Keto Sulfones

A one-step strategy for the synthesis of α-methenyl ketones from β-keto sufones is reported. Success of the methodology is elaborated for the synthesis of chromanones and isoflavanones in one-step.

Tandem Alkyne Hydroacylation and Oxo-Michael Addition: Diastereoselective Synthesis of 2,3-Disubstituted Chroman-4-ones and Fluorinated Derivatives

Tandem reactions involving Rh-catalyzed intermolecular hydroacylations of alkynes with salicylaldehydes followed by intramolecular oxo-Michael additions are described for the diastereoselective synthesis of 2,3-disubstituted chroman-4-ones. The tandem hydroacylation/oxo-Michael additions occur to form 2,3-disubstituted chroman-4-ones in high yields from a range of 1,2-disubstituted acetylenes and substituted salicylaldehyes. The resulting 2,3-disubstituted chroman-4-ones are readily fluorinated to form trans-3-fluoro-2,3-disubstituted chroman-4-ones in high yields with excellent diastereoselectivity. (Chemical Equation Presented).

Intermolecular C-O addition of carboxylic acids to arynes: Synthesis of o-hydroxyaryl ketones, xanthones, 4-chromanones, and flavones

An efficient and simple route to biologically and pharmaceutically important o-hydroxyaryl ketones, xanthones, 4-chromanones, and flavones has been developed utilizing readily available carboxylic acids and commercially available o-(trimethylsilyl)aryl tr

Radical-involved photosynthesis of AuCN oligomers from Au nanoparticles and acetonitrile

We show here the first radical route for the direct photosynthesis of AuCN oligomers with different sizes and shapes, as evidenced by TEM observations, from an Au nanoparticle/benzaldehyde/CH3CN ternary system in air under UV-light irradiation. This photochemical route is green, mild, and universal, which makes itself distinguishable from the common cyanidation process. Several elementary reaction steps, including the strong C-C bond dissociation of CH3CN and subsequent ?CN radical addition to Au, have been suggested to be critical in the formation of AuCN oligomers based on the identification of ?CN radical by in situ EPR and the radical trapping technique, and other reaction products by GC-MS and 1H NMR, and DFT calculations. The resulting solid-state AuCN oligomers exhibit unique spectroscopic characters that may be a result of the shorter Au-Au distances (namely, aurophilicity) and/or special polymer-like structures as compared with gold cyanide derivatives in the aqueous phase. The nanosized AuCN oligomers supported on mesoporous silica showed relatively good catalytic activity on the homogeneous annulation of salicylaldehyde with phenylacetylene to afford isoflavanones employing PBu3 as the cocatalyst under moderate conditions, which also serves as evidence for the successful production of AuCN oligomers.

Convenient synthesis of chromones and quinolinones

A one pot synthesis of substituted chromones and quinolinones by condensing commercially available and cheaper molecules like salicylic acid and anthranilic acid respectively with alkenes / nitriles followed by insitu cyclization using ammonium acetate as base has been achieved.

Highly selective palladium-catalyzed direct c-h α-monoarylation of carbonyl compounds using water containing the surfactant polyoxyethylene- α-tocopheryl sebacate (PTS) as a solvent

Highly selective direct C-H α-monoarylation reactions of 4-chromanones, ketones and 2-phenylacetaldehyde with aryl halides have been performed in satisfactory yields by using a tris(dibenzylideneacetone) dipalladium(0)/tri-tert-butylphosphine tetrafluoroborate catalyst system, potassium bicarbonate as the base and a solvent consisting of pure water containing a small amount of polyoxyethylene-α-tocopheryl sebacate (PTS). Analogous reaction conditions have been employed in a tandem process leading to phenyl-substituted isocoumarins from carbonyl compounds and methyl 2-bromobenzoate.