13057-72-2

Basic information

• Product Name: 7-Hydroxyisoflavone
• Synonyms: 3-Phenyl-7-hydroxy-4H-1-benzopyran-4-one;7-Hydroxy-3-phenyl-4H-1-benzopyran-4-one;7-Hydroxy-3-phenylchromone;Ipriflavone Impurity 1;7-Hydroxy-3-phenyl-4H-chromen-4-one AldrichCPR;4H-1-Benzopyran-4-one, 7-hydroxy-3-phenyl-;7-hydroxy-3-phenyl-4-chromenone;Isoflavone, 7-hydroxy- (6CI,7CI,8CI)
• CAS NO: 13057-72-2
• Molecular Formula: C₁₅H₁₀O₃
• Molecular Weight: 238.24
• Product Categories: Iso-Flavones
• Mol File: 13057-72-2.mol

Chemical Properties

• Melting Point: 214.0 to 218.0 °C
• Boiling Point: 450.1 °C at 760 mmHg
• Flash Point: 176.3 °C
• Appearance: /
• Density: 1.34 g/cm³
• Vapor Pressure: 1.02E-08mmHg at 25°C
• Refractive Index: 1.666
• PKA: 6.98±0.20(Predicted)
• CAS DataBase Reference: 7-Hydroxyisoflavone(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Hydroxyisoflavone(13057-72-2)
• EPA Substance Registry System: 7-Hydroxyisoflavone(13057-72-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: DJ3100255
• HazardClass: IRRITANT
• Hazardous Substances Data: 13057-72-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
7-Hydroxyisoflavone is used as a drug intermediate for the development of medicines that address various health conditions. Its applications include:
1. Antiosteoporosis Drugs:
7-Hydroxyisoflavone is used as an active pharmaceutical ingredient in the development of antiosteoporosis drugs, helping to prevent bone loss and maintain bone health.
2. Prevention of Knubbly Cell Diffusion:
The compound is utilized in medicines that prevent the diffusion of knubbly cells, which can lead to various health issues.
3. Therapy for Coronary Heart Disease:
7-Hydroxyisoflavone is also used in the formulation of drugs that provide therapy for coronary heart disease, aiding in the treatment and management of this cardiovascular condition.

InChI:InChI=1/C15H10O3/c16-11-6-7-12-14(8-11)18-9-13(15(12)17)10-4-2-1-3-5-10/h1-9,16H

Upstream product

• 3669-41-8 1-(2,4-dihydroxyphenyl)-2-phenylethanone 
• 109-94-4 formic acid ethyl ester 
• 68-12-2 N,N-dimethyl-formamide 
• 60-29-7 diethyl ether 
• 95280-34-5 3-(2,4-dimethoxy-phenyl)-3-oxo-2-phenyl-propionaldehyde 
• 7727-15-3 aluminium bromide 
• 71-43-2 benzene 
• 15485-72-0 ethyl 7-hydroxy-4-oxo-3-phenyl-4H-chromene-2-carboxylate 
• 103-82-2 phenylacetic acid 
• 124-63-0 methanesulfonyl chloride 
• 109-63-7 boron trifluoride diethyl etherate 
• 39238-04-5 7-hydroxy-4-oxo-3-phenyl-4H-chromene-2-carboxylic acid 
• 110-89-4 piperidine 
• 110-86-1 pyridine 

Downstream Products

• 35212-22-7 Ipriflavone 
• 19816-36-5 6,8-dibromo-7-hydroxyisoflavone 
• 19816-42-3 7-hydroxy-8-iodoisoflavone 
• 35486-69-2 3-phenyl-8,8-dimethyl-4-oxo-4H,8H-benzo[1,2-b:3,4-b']dipyran 
• 66346-74-5 7-(3-methylbut-2-enyloxy)-3-phenyl-4H-chromen-4-one 
• 13057-73-3 7-ethoxy-3-phenyl-chromen-4-one 
• 114889-31-5 4-oxo-3-phenyl-4H-furo[2,3-h]chromene-8-carboxylic acid ethyl ester 
• 111441-76-0 4-hydroxy-5-phenylacetyl-benzofuran-2-carboxylic acid ethyl ester 
• 109566-56-5 4-oxo-3-phenyl-4H-furo[2,3-h]chromene-8-carboxylic acid 
• 20594-05-2 7-O-(β-D-glucopyranosyl)-3-phenyl-4H-chromen-4-one 
• 121587-71-1 8,9-dihydro-8-methyl-3-phenylfuro<2,3-h>-1-benzopyran-4(H)-one 
• 121587-74-4 (7-Hydroxy-4-oxo-3-phenyl-4H-chromen-8-yl)-acetaldehyde 
• 121587-73-3 8-methyl-3-phenylfuro<2,3-h>-1-benzopyran-4(H)-one 
• 121587-66-4 7-hydroxy-8-(prop-2-enyl)-3-phenyl-<4H>-1-benzopyran-4-one 

Relevant articles and documents

The oxidative coupling between benzaldehyde derivatives and phenylacetylene catalyzed by rhodium complexes via C-H bond activation

This paper reports the use of rhodium (Rh) catalysts for the oxidative coupling reaction between phenylacetylene and benzaldehyde derivatives via C-H bond activation. These reactions were catalyzed by Rh(l-amino acid)(cod) (the l-amino acid is l-phenylala

CYTISINE-LINKED ISOFLAVONOID ANTINEOPLASTIC AGENTS FOR THE TREATMENT OF CANCER

Cytisine-linked isoflavonoids, or pharmaceutically acceptable salts thereof or pharmaceutically acceptable compositions thereof, are useful for the treatment of conditions in which cells have a reliance on peroxisomal HSD17B4 to degrade very long chain fatty acids and provide necessary energy for cell proliferation, such as is seen in colorectal cancer and prostate cancer, for example.

Synthesis and biological evaluation of Complex I inhibitor R419 and its derivatives as anticancer agents in HepG2 cells

In this study, Complex I inhibitor R419 was firstly revealed to have significant anticancer activity against HepG2 cells (IC50 = 5.2 ± 0.9 μM). Based on this finding, a series of R419 derivatives were synthesized and biologically evaluated. As results, 9 derivatives were found to have obvious anticancer activity. Among them, H20 exhibited the most potent activity (IC50 = 2.8 ± 0.4 μM). Mechanism study revealed that H20 caused severe depletion of cellular ATP, dose-dependently activated AMPK, decreased Bcl-2/Bax ratio and induced necrotic cell death. Most importantly, H20 displayed definite inhibitory activity against Complex I.

Developing antineoplastic agents that target peroxisomal enzymes: Cytisine-linked isoflavonoids as inhibitors of hydroxysteroid 17-beta-dehydrogenase-4 (HSD17B4)

Cytisine-linked isoflavonoids (CLIFs) inhibited PC-3 prostate and LS174T colon cancer cell proliferation by inhibiting a peroxisomal bifunctional enzyme. A pull-down assay using a biologically active, biotin-modified CLIF identified the target of these agents as the bifunctional peroxisomal enzyme, hydroxysteroid 17β-dehydrogenase-4 (HSD17B4). Additional studies with truncated versions of HSD17B4 established that CLIFs specifically bind the C-terminus of HSD17B4 and selectively inhibited the enoyl CoA hydratase but not the d-3-hydroxyacyl CoA dehydrogenase activity. HSD17B4 was overexpressed in prostate and colon cancer tissues, knocking down HSD17B4 inhibited cancer cell proliferation, suggesting that HSD17B4 is a potential biomarker and drug target and that CLIFs are potential probes or therapeutic agents for these cancers.

Development of a general approach to the synthesis of a library of isoflavonoid derivatives

Isoflavonoids are a class of organic compounds that act primarily as antioxidants. They are produced almost exclusively by various members of the bean family including soybeans, tofu, peanuts, chick peas, and alfalfa. The antioxidant characteristics that isoflavonoids exhibit help hinder the progression of certain cancers, primarily breast, prostate, and colon cancer. We have developed a three-five step synthesis for obtaining a suite of isoflavonoid derivatives. The synthesis involves an enamine formation, a ring closure and halogenation, a Suzuki coupling, and finally a global deprotection to obtain the respective isoflavonoid derivatives.

Synthesis and biological evaluation of pyranoisoflavone derivatives as anti-inflammatory agents

In this paper, barbigerone (1a) and its twenty-seven related structural analogues were synthesized via complementary synthetic routes and their anti-inflammatory effects on the expression of TNF-α in LPS-stimulated splenocytes were evaluated. Among these compounds, 1a, 1d, 1f and 1g were found to remarkably inhibit TNF-α production. Furthermore, 1g showed the most potent and dose-dependent manner inhibitory effect on TNF-α release, with better IC50 value (3.58 μM) than barbigerone (8.46 μM). Oral administration of 1g at 20 mg/kg/day for two weeks obviously demonstrated protective effect in adjuvant-induced arthritis models as evaluated by clinical score of paws, and histological examination of joint tissues from rats. Mechanism studies on mRNA and protein level suggested that 1g inhibited the TNF-α production via depressing TNF-α converting enzyme (TACE) mRNA expression. In conclusion, these data show 1g with potential therapeutic effects as an anti-inflammatory agent.

In vitro study of isoflavones and isoflavans as potent inhibitors of human 12- and 15-lipoxygenases

In this study, we have investigated 16 isoflavone and isoflavan derivatives as potential inhibitors of human lipoxygenase (platelet 12-lipoxygenase, reticulocyte 15-lipoxygenase-1, and epithelial 15-lipoxygenase-2). The flavonoid baicalein, a known lipoxygenase inhibitor, was used as positive control. Four compounds, 6,7-dihydroxy-3′-chloroisoflavone (1c), 7-hydroxy-8-methyl-4′-chloroisoflavan (5a), 7,8-dihydroxy-4′-methylisoflavan (5b), and 7,8-dihydroxy-3′-methylisoflavan (5c), were effective inhibitors of 12-lipoxygenases and 15-lipoxygenase-1 with IC50's i values in the range of 0.3-3 μm.

Novel synthesis of 3-phenyl-chromen-4-ones using n-heterocyclic carbene as organocatalyst: An efficient domino catalysis type approach

Herein is reported a simple and efficient synthesis of isoflavones starting from various substituted phenacyl bromides and salicylaldehydes in presence of NHC. The mechanism involved domino catalysis type approach with consumption and regeneration of catalyst in two catalytic cycles. This method proved to be very lucrative and gives very good yield. The method described here represents an environmentally benign alternative to classical approach.

A mild and efficient protocol to synthesize chromones, isoflavones, and homoisoflavones using the complex 2,4,6-trichloro-1,3,5-triazine/ dimethylformamide

A mild and efficient one-flask method has been developed for the synthesis of chromones, isoflavones, and homoisoflavones from 2-hydroxyacetophenones, deoxybenzoins, and dihydrochalcones, respectively, via one-carbon extension using the complex 2,4,6-trichloro-1,3,5-triazine/dimethylformamide. Deoxybenzoins and dihydrochalcones were prepared in situ by the reaction of readily available substituted phenols with phenylacetic acids and 3-phenylpropanoic acids, respectively. This method allows the synthesis of a wide range of compounds with multiple phenolic hydroxyls and other substituents. The methodology has been applied to the synthesis of three naturally occurring isoflavones such as formononetin (9c), daidzein (9d), and retusin (9h).

Synthesis and structural study on heterocyclic compounds 7-decanoyloxy-3-(4′-substitutedphenyl)-4H-1-benzopyran-4-ones: Crystal structure of 7-decanoyloxy-3-(4′-methylphenyl)-4H-1-benzopyran-4-one

Six new isoflavone-based esters, 7-decanoyloxy-3-(4′-substitutedphenyl)-4H-1-benzopyran-4-ones, derived from 1,3-benzenediol (resorcinol) and different para substituted phenylacetic acids have been synthesized and characterized. The molecular structures of the title compounds were elucidated with the employment of physical measurements and spectroscopic techniques (FTIR, 1D and 2D NMR). The conformation of 7-decanoyloxy-3-(4′-methylphenyl)-4H-1-benzopyran-4-one was determined by single crystal X-ray diffraction analysis of which the title compound crystallized into triclinic lattice with P-1 space group. Crystal structure of the title compound also revealed that the two phenyl rings of the central moiety were planar whilst the heterocyclic ring was found to pucker slightly from the mean plane.