4233-35-6

Usage

General Description

1,3-Propanedione, 1-(3,4-dimethoxyphenyl)-3-(2-hydroxyphenyl)- is a chemical compound that is commonly used in the production of pharmaceuticals, fragrances, and flavors. It is a ketone compound with a complex molecular structure, containing two aromatic rings and a ketone functional group. 1,3-Propanedione, 1-(3,4-dimethoxyphenyl)-3-(2-hydroxyphenyl)- is known for its sweet, floral scent and is used in the formulation of perfumes and colognes. It also has potential therapeutic applications, such as in the treatment of certain medical conditions. Additionally, it can be used as a flavoring agent in food products, adding a unique and pleasant taste to various food and beverage items.

Upstream product

• 67858-33-7 2-acetylphenyl-3,4-dimethoxybenzoate 
• 136003-88-8 1-[2-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-3-(3,4-dimethoxy-phenyl)-propane-1,3-dione 
• 118-93-4 o-hydroxyacetophenone 
• 3535-37-3 3,4-dimethoxybenzoic acid chloride 
• 69404-96-2 methyl-2-<(tert-butyldimethylsilyl)oxy>benzoate 
• 119-36-8 methyl salicylate 
• 93-07-2 Veratric acid 
• 582-24-1 1-phenyl-2-hydroxyethanone 

Downstream Products

• 4143-62-8 3',4'-dimethoxyflavone 
• 93321-88-1 2-(3,4-dimethoxy-phenyl)-chromene-4-thione 
• 1198005-58-1 3,4-dimethoxybenzoic acid 2-(3-ethoxycarbonylbut-3-enoyl)phenyl ester 
• 1417318-17-2 3',4'-dimethoxy-3-(3,4-dimethoxyphenyl)flavone 
• 491-38-3 1-benzopyran-4(4H)-one 
• 55168-26-8 trans-1-(2-Hydroxybenzoyl)-2-(4-oxo-4H-<1>benzopyran-3-yl)-ethylen 

Relevant academic research and scientific papers

In vitro photoprotective evaluation and development of novel nanoemulsion with chromone derivative

Chromone derivatives exhibiting high absorbance values in the UVA/UVB region were synthesized, and their photoprotective properties were evaluated. Chromones were prepared according to known literature procedures and characterized by high resolution mass

Rational design for multicolor flavone-based fluorophores with aggregation-induced emission enhancement characteristics and applications in mitochondria-imaging

Fluorophores with aggregation-induced emission enhancement (AIEE) properties have attracted more attention in recent years. In order to realise more valuable applications, the different kinds of AIEE molecules are in serious need of further development. Therefore, a novel flavone-based AIEE system derived from restriction of intramolecular rotation (RIR) was designed and synthesized in this work. The results revealed that six of the compounds showed typical AIEE characteristics, with fluorescence emissions from purple, blue, cyan to green, tunable by changing substituent groups. This flavone-based AIEE system has never been reported before. The AIEE characteristics were investigated by optical spectroscopy, fluorescence photographs, scanning electron microscopy (SEM), fluorescence quantum yields (φF) and fluorescence lifetime in the CH3OH/H2O mixed solution. Moreover, benefiting from the simple structures and small molecular weight, they could permeate cells faster than current high-molecular-weight AIEE molecules. Furthermore, to examine possible biomedical applications, fluorescence imaging in living A549 lung cells and cell viabilities were examined, and the results displayed that these fluorophores showed good cellular uptake and low cytotoxicity within the experimental concentration range. In addition, these AIEE compounds possessed excellent specificity for mitochondrial targeting and mitochondrial morphological change tracking, besides, they displayed superior photostability, which indicated they are potential candidates for mitochondrial imaging.

One-Pot Synthesis of Benzopyran-4-ones with Cancer Preventive and Therapeutic Potential

A one-pot synthesis of novel benzopyran-4-ones is described. In a tandem reaction, organobase-catalysed Michael addition of R1COCH2COR2 on chromone-3-carboxylic acid led to decarboxylation and pyran-4-one ring opening of the latter. This was followed by chromone-and/or chromanone ring closure of the resulting Michael adducts when R1 is an ortho-hydroxyaryl group. Antioxidant testing of 14 derivatives identified strong antiradical properties of chromanones 3o-r (2.1-3.1 μmol Trolox equiv./μmol compound in the DPPH assay). Chromanones 3p and 3r and 2-styrylchromone 3k were also most potent in inducing the cytoprotective Keap1-Nrf2 signalling pathway in a reporter gene assay (fivefold induction at concentrations 3 μM). Of the seven compounds evaluated for antiproliferative activities, 3k and 3r were the most active, inhibiting leukaemia K562 cell proliferation by 50 % after 72 h at concentrations of 4.5 and 7.9 μM, whereas normal peripheral blood mononuclear cells were not affected. Chromanones 3p and 3r and 2-styrylchromones 3k potently activate the Nrf2 response in the AREc32 cell line at low micromolar concentrations (C5 3 μM). Compounds 3k and 3r are also the most active in inhibiting cell proliferation by 50 % after 72 h incubation at concentrations of 4.5 and 7.7 μM, whereas normal peripheral blood mononuclear cells were not affected.

Synthesis of B-ring substituted flavones and evaluation of their antitumor and antioxidant activities

A series of flavones, substituted at the ring B, were synthesized using either Claisen-Schimdt Condensation or Baker-Venkataraman rearrangement. The synthesized compounds were tested for in vitro cytotoxic activity by sulforhodamine B assay against three cell lines of different origin, viz. HepG2, MCF-7, and MOLT-4. The compounds were also tested for a possible antioxidant activity by determination of inhibition of lipid peroxidation. Quercetin was taken as a standard for antioxidant activity. Compound 1c showed the highest cytotoxic activity against MCF-7 (GI50 0.1 μM) and MOLT-4 (GI50 0.1 μM) cell lines and was comparable to adriamycin, the standard used. Compounds 1b, 1g, and 1h also showed promising activity against MCF-7 and MOLT-4 cell lines. In the absence of a hydroxyl group, one or more methoxy groups present on the B-ring (compounds 1c-1e) were major determinants of inhibition of lipid peroxidation.

Structure activity relationship studies of some potent antifungal flavones, 4-thioflavones and 4-iminoflavones

A series of flavones, carrying halogens, methoxy and nitro groups at various positions were synthesized by the Baker-Venkataraman rearrangement and were subsequently converted to 4-thioflavones and 4-iminoflavones. The synthesized compounds were evaluated for their in vitro antifungal activity against Trichophyton longifusus, Candida albicans, Aspergillus flavus, Microsporum canis, Fusarium solani and Candida glabrata. All synthesized compounds showed significant activity against T. longusus, A. flavus, M. canis and F. Solani but inactive against C. albicans and C. glabrata, respectively. 2-phenyl-4H-1-benzopyran-4-thiones were relatively more active than flavones and 4-iminoflavones. However, some compounds were even more active than standard miconazol and amphotericin B drugs.

Synthesis and antibacterial activity of substituted flavones, 4-thioflavones and 4-iminoflavones

Synthesis of flavones, 4-thioflavones and 4-iminoflavones was carried out with the substitution of variable halogens, methyl, methoxy and nitro groups in the A, B and AB rings of the respective compounds and we also report here their antibacterial activity. Most of the synthesized compounds were found to be active against Escherichia coli, Bacillus subtilis, Shigella flexnari, Salmonella aureus, Salmonella typhi and Pseudomonas aeruginosa. Activity of 4-thioflavones and 4-iminoflavones was found to be higher than that of their corresponding flavone analogues. Investigated compounds having substituents like F, OMe and NO2 at 4′-position in ring-B exhibited enhanced activity and the presence of electronegative groups in the studied compounds showed a direct relationship to the antibacterial activity.

A practical synthesis of flavones from methyl salicylate

A facile synthetic method has been developed for the conversion of methyl salicylate (5) into flavones 1a-i in high yields. Compound 5 on treatment with t-butyldimethylsilyl chloride (6) gave the O-silyl protected ester 7. Condensation of this ester 7 with the lithium anion generated from acetophenones 3a-i yielded the 1.3-diarylpropane-1,3-diones 8a-i, which on treatment with glacial acetic acid containing 0.5% H2SO4 for 3 h at 95-100°C provided the desired flavones 1a-i in 83-94% yields.

Structural Studies on Bio-active Compounds. Part 12. Tautomerism and Conformation of Aryl-substituted 1-(2-Hydroxyphenyl)-3-phenylpropane-1,3-diones in the Solid Phase and in Solution

The tautomerism of a series of aryl-substituted 1-(2-hydroxyphenyl)-3-phenylpropane-1,3-diones has been studied in deuteriochloroform solution by 1H n.m.r. techniques and, in the case of 1-(2-hydroxy-4-methoxyphenyl)-3-phenylpropane-1,3-dione and 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylpropane-1,3-dione, in the solid state by X-ray crystallography.Of these compounds, most exist between 80 and 95percent in the enolised form in solution and 1-(2-hydroxy-4-methoxyphenyl)-3-phenylpropane-1,3-dione adopts this tautomer in the crystal.However, 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylpropane-1,3-dione is present as the diketone in the solid phase and enolises very slowly in solution. 1-(6-Benzoyloxy-2-hydroxyphenyl)-3-hydroxy-3-phenylprop-2-en-1-one is shown by 1H n.m.r. spectroscopy possibly to adopt a 'coiled' conformation in solution in deuteriochloroform.