67029-87-2

Usage

Source

Naturally occurring compound found in the spice turmeric

Traditional Medicine Use

Anti-inflammatory and antioxidant properties

Health Benefits

a. Reduces the risk of chronic diseases such as cancer, heart disease, and Alzheimer's
b. Manages and relieves symptoms of inflammatory conditions like arthritis
c. Supports liver and digestive health

Research

Subject of numerous studies for its potential health benefits

Structure

Contains a phenyl group, a propane-1,3-dione group, and a hydroxy-methoxyphenyl group

Appearance

Yellow crystalline solid

Solubility

Soluble in dimethyl sulfoxide (DMSO), slightly soluble in water, and insoluble in nonpolar solvents like hexane

Stability

Relatively stable under normal conditions, but can degrade under extreme heat or light exposure

Bioavailability

Low bioavailability in its natural form, often improved with the use of adjuvants or formulations

Safety

Generally considered safe for consumption, but high doses may cause gastrointestinal upset in some individuals

Applications

Used as a natural coloring agent, in the food industry, and as a dietary supplement for its potential health benefits.

Upstream product

• 127745-66-8 2-(benzyloxy)-5-(methoxy)acetophenone 
• 110624-04-9 4-methoxyphenyl benzoylacetate 
• 490-78-8 2,5-Dihydroxyacetophenone 
• 98-88-4 benzoyl chloride 
• 87428-52-2 2-hydroxy-3'-methoxyacetophenone 
• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 
• 20718-17-6 2-(dimethyl(oxo)-λ⁶-sulfaneylidene)-1-phenylethan-1-one 
• 110623-98-8 4-methoxyphenyl 3-(ethylenedioxy)-3-phenylpropanoate 
• 85892-91-7 2-(2-phenyl-1,3-dioxolan-2-yl)acetic acid 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 27773-03-1 ethyl 3,3-(ethylenedioxy)-3-phenylpropanoate 
• 705-15-7 1-(2-hydroxy-5-methoxyphenyl)ethan-1-one 

Downstream Products

• 138580-54-8 5-(2-hydroxy-5-methoxyphenyl)-3-phenylpyrazole 
• 215999-39-6 3-bromo-6-methoxy-2-phenyl-4H-chromen-4-one 
• 136764-57-3 1a,7a-Dihydro-5-methoxy-1a-phenyl-7H-oxireno<1>benzopyran-7-one 
• 26964-24-9 6-methoxyflavone 

Relevant academic research and scientific papers

Trypanocidal activity of flavanone derivatives

Chagas disease, also known as American trypanosomiasis, is classified as a neglected disease by the World Health Organization. For clinical treatment, only two drugs have been on the market, Benznidazole and Nifurtimox, both of which are recommended for use in the acute phase but present low cure rates in the chronic phase. Furthermore, strong side effects may result in discontinuation of this treatment. Faced with this situation, we report the synthesis and trypanocidal activity of 3-benzoyl-flavanones. Novel 3-benzoyl-flavanone derivatives were prepared in satisfactory yields in the 3-step synthetic procedure. According to recommended guidelines, the whole cell-based screening methodology was utilized that allowed for the simultaneous use of both parasite forms responsible for human infection. The majority of the tested compounds displayed promising anti-Trypanosoma cruzi activity and the most potent flavanone bearing a nitrofuran moiety was more potent than the reference drug, Benznidazole.

Rh(III)-Catalyzed Aldehydic C?H Functionalization Reaction between Salicylaldehydes and Sulfoxonium Ylides

A novel aldehydic C?H functionalization reaction between salicylaldehydes and sulfoxonium ylides has been developed under rhodium(III) catalysis, affording coupling products in moderate to good yields. A plausible mechanism involving aldehydic C(sp2)?H activation by rhodium(III) and rhodium(III) catalyzed carbene insertion is also proposed. It was also found that the aldehydic C?H functionalization followed by dehydrative cyclization was able to produce flavonoids in one-pot. (Figure presented.).

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.

Design, synthesis and structure-activity relationships of 3,5-diaryl-1H-pyrazoles as inhibitors of arylamine N-acetyltransferase

The synthesis and inhibitory potencies of a novel series of 3,5-diaryl-1H-pyrazoles as specific inhibitors of prokaryotic arylamine N-acetyltransferase enzymes is described. The series is based on hit compound 1 3,5-diaryl-1H-pyrazole identified from a high-throughout screen that has been carried out previously and found to inhibit the growth of Mycobacterium tuberculosis.

Convenient one-pot synthesis of chromone derivatives and their antifungal and antibacterial evaluation

A one-pot method for the synthesis of chromone derivatives from the reaction of 2-hydroxyacetophenones with aliphatic or aromatic acid chlorides is reported. Esterification and Baker-Venkataraman rearrangement were promoted by t-BuOK, which was followed directly by acid-catalyzed cyclization in one pot. Some of 2-cyclohexyl- and 2-cyclohexylmethyl-substituted chromones displayed activity against plant pathogenic fungal strains. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications1 to view the free supplemental file. Copyright Taylor & Francis Group, LLC.

An efficient synthesis of 3-bromoflavones under solvent free conditions using grinding technique

Selective bromination of 1-(2-hydroxyphenyl)-3-phenylpropane- 1,3-diones has been carried out with ammonium bromide and ammonium persulphate at room temperature using grinding technique under solvent free conditions to give 2-bromo derivatives which on cyclodehydration with p-toluenesulphonic acid under grinding conditions give 3-bromoflavones. Also, flavones on bromination using above mentioned conditions give 3-bromoflavones directly.

Photohydrodimerization of 6-methoxyflavone to 6,6″-dimethoxy-2, 2″-biflavanones

6-Methoxyflavone (7) easily afforded two hydrodimers of rac-6,6″-dimethoxy-2,2″-biflavanone (8a) and meso-6,6″- dimethoxy-2,2″-biflavanone (8b) and one reductive product of 6-methoxyflavanone (9) by using photolysis with the electron-donating amines including triethylamine, 2-(N,N-dimethylamino)ethanol or N,N-dimethylaniline in solvents of acetonitrile, benzene or methylene dichloride. They were found to give higher yields of rac-6,6″-dimethoxy-2,2″-biflavanone (8a) and meso-6,6″-dimethoxy-2,2″-biflavanone (8b) (38.7% and 4.5%, 35.3% and 6.2%, respectively) in the reaction conditions of 1/10 molar ratio of 6-methoxyflavone (7) to triethylamine in a solvent of acetonitrile with irradiation of twenty-four hours by using 306 nm and 352 nm lamps.

Epoxidation of Flavones by Dimethyldioxirane

The synthesis of epoxides 2 by epoxidation of flavones 1 with isolated dimethyldioxirane (as acetone solution) at subambient temperatures is reported.These labile epoxides were isolated and completely characterized by UV, IR, 1H and 13C NMR, MS, and C,H analyses.Warming to room temperature led to rearrangement to afford quantitatively the 3-hydroxyflavones 3b,h,i,n.Treatment of the epoxides 2b,f with methanol led to the 3-hydroxy-2-methoxyflavanones 4b,f, as a mixture of cis and trans isomers.

PHOTOLYSIS OF CYCLIC ACETALS OF ARYL BENZOYLACETATES AS THE KEY STEP IN A NEW SYNTHESIS OF FLAVONES

Although the yields found for the photo-Fries rearrangement of the aryl benzoylacetates 1 are poor, blocking of the carbonyl group, as in the related acetal derivatives 3, results in a substantial preparative improvement.Thus, the o-hydroxydibenzoylmethanes 2 are obtained from 1 with an average yield of 18percent, while the corresponding acetals 4 are obtained from 3 with an average yield of 58 percent.Compounds 4 are efficiently converted into flavones 8 by means of wet silica gel, through hydrolysis of the acetal moiety and subsequent cyclization of the resulting o-hydroxydibenzoylmethanes 2.