6297-64-9

Usage

Source

Root of the turmeric plant

Classification

Polyphenol

Traditional Medicine Use

Antioxidant and anti-inflammatory properties

Modern Research

Potential anti-cancer effects, brain function improvement, and heart disease risk reduction

Additional Uses

Food additive and coloring agent

Color

Bright yellow

Versatility

Wide range of potential health benefits

Upstream product

• 5271-67-0 2-Thiophenecarbonyl chloride 
• 118-93-4 o-hydroxyacetophenone 
• 527-72-0 2-thiophenylcarboxylic acid 
• 2810-04-0 Ethyl thiophene-2-carboxylate 

Downstream Products

• 6297-63-8 2-(2-thienyl)-4H-1-benzopyran-4-one 
• 65485-94-1 C₁₈H₁₂O₄S 
• 1333334-76-1 2-[3-oxo-3-(thiophen-2-yl)propanoyl]phenyl acetate 
• 1286237-44-2 2-(thiophen-2-yl)-4H-chromene-4-thione 
• 1435773-33-3 3-(4-(tert-butoxy)benzyl)-1-(thiophen-2-yl)chromeno[2,3-c]pyrrol-9(2H)-one 
• 1433961-79-5 3-(4-hydroxybenzyl)-1-(thiophen-2-yl)chromeno[2,3-c]pyrrol-9(2H)-one 
• 1438433-40-9 1-(2-hydroxyphenyl)-4-(thiophen-2-yl)butane-1,4-dione 

Relevant academic research and scientific papers

On the role of the vinylsulfoxide side chain of dirchromone towards its bioactivities

Analogs of dirchromone were prepared to shed light on the pivotal role of its peculiar vinylsulfoxide side chain towards its cytotoxic and antimicrobial properties, especially dependant upon the presence and oxidation state of sulfur. The reaction of dirchromone with cysteamine revealed a surprising Michael acceptor behavior with elimination of the methylsulfinyl moiety and redox transformation of the sulfur atom that could be involved in the mode of action of dirchromone within cells.

Synthesis, photophysical and electrochemical properties of novel and highly fluorescent difluoroboron flavanone β-diketonate complexes

Difluoroboron β-diketonates complexes are highly luminescent with extensive properties such as their fluorescence both in solution and in solid state and their high molar extinction coefficients. Due to their rich optical properties, these compounds have been studied for their applications in organic electronics such as in self-assembly and applications in biosensors, bio-imaging and optoelectronic devices. The easy and fast synthesis of difluoroboron β-diketonate (BF2dbm) complexes makes their applications even more attractive. Although many different types of difluoroboron β-diketonates complexes have been studied, the cyclic flavanone analogues of these compounds have never been reported in the literature. Therefore, the present work aims to synthesize difluouroboron flavanone β-diketonate complexes, study their photophysical and electrochemical properties and assess their suitability for applications in optoelectronic devices. The synthesis was based on a Baker-Venkataraman reaction which initially provided substituted diketones, which were subsequently reacted with aldehydes to afford the proposed flavanones. The complexation was achieved by reacting flavanones and BF3·Et2O and in total 9 novel compounds were obtained. A representative difluoroboron flavanone complex was subjected to single crystal X-ray diffraction to unequivocally confirm the chemical structure. A stability study indicated only partial degradation of these compounds over a few days in a protic solvent at elevated temperatures. Photophysical studies revealed that the substituent groups and the solvent media significantly influence the electrochemical and photophysical properties of the final compounds, especially the molar absorption coefficient, fluorescence quantum yields, and the band gap. Moreover, the compounds exhibited a single excited-state lifetime in all studied solvents. Computational studies were employed to evaluate ground and excited state properties and carry out DFT and TDDFT level analysis. These studies clarify the role of each state in the experimental absorption spectra as well as the effect of the solvent.

Transition-Metal-Free Photoinduced Intramolecular Annulation of 2,3-Di(hetero)arylchromen-4-one

An efficient transition-metal-free photoinduced intracyclization of 4H-chromen-4-ones in EtOH-H2O (7:1, v/v) at ambient temperature for the construction of complicated fused-ring heteroaromatics is established. The reaction proceeds smoothly without requiring any catalysts/additives.

One-pot synthesis of 3-(furan-2-yl)-4: H -chromen-4-ones from 1-(2-hydroxyphenyl)butane-1,3-diones and 2,5-dimethoxy-2,5-dihydrofuran catalyzed via K10 montmorillonite under solvent-free conditions

A new, concise and efficient method of one-pot synthesis of 3-(furan-2-yl)-4H-chromen-4-ones was developed using K10 montmorillonite catalysis under solvent-free conditions. The procedure of the synthesis of 3-(furan-2-yl)-4H-chromen-4-ones was that 1-(2-hydroxyphenyl)butane-1,3-diones and 2,5-dimethoxy-2,5-dihydrofuran underwent a process of α-alkoxyalkylation in the presence of K10 montmorillonite at 80 °C for 0.5 h and continuously at 120 °C for another 0.5 h. The advantages of this method were that it was solvent-free, the K10 montmorillonite was recyclable and it had an easy work-up.

Synthesis of new fluorescent 1-(thien-2-yl)-9H-thieno[3,4-b]-chroman-9-ones and their fluorescent photomodulation by photochromic dihetarylethenes

New fluorescent derivatives of 1-(thien-2-yl)-3-methyl-9H-thieno[3,4-b]-chroman-9-one are synthesized and their spectral properties studied. The prepared fluorescent compounds are combined with several photochromic benzothienyl dihetarylethenes to provide

Discovery of 3-(4-hydroxybenzyl)-1-(thiophen-2-yl)chromeno[2,3-c]pyrrol- 9(2H)-one as a phosphodiesterase-5 inhibitor and its complex crystal structure

Phosphodiesterase-5 (PDE5) inhibitors have been approved for the treatment of erectile dysfunction and pulmonary hypertension, but enthusiasm on discovery of PDE5 inhibitors continues for their potential new applications. Reported here is discovery of a series of new PDE5 inhibitors by structure-based design, molecular docking, chemical synthesis, and enzymatic characterization. The best compound, 3-(4-hydroxybenzyl)-1-(thiophen-2-yl)chromeno[2,3-c]pyrrol-9(2H)-one (57), has an IC50 of 17 nM against the PDE5 catalytic domain and good selectivity over other PDE families. The crystal structure of the PDE5 catalytic domain in complex with 57 was determined at 2 A resolution and showed that 57 occupies the same pocket as other PDE5 inhibitors, but has a different binding pattern in detail. On the basis of the binding pattern of 57, a novel scaffold can be proposed as a candidate of PDE inhibitors.

Synthesis of multi-functionalized chromeno[2, 3-c]pyrrol-9(2H)-ones: Investigation and application of Baker-Venkataraman rearrangement involved reactions catalyzed by 4-(Dimethylamino)pyridine

An efficient one-pot synthesis of multi-functionalized chromeno[2, 3-c]pyrrol-9(2H)-ones from 1, 3-diaryl-1, 3-diket-ones and amino acids is described. The synthesis is based on the 4-(dimethylamino)pyridine-catalyzed Baker-Venkatara-man rearrangement and

Synthesis and properties of photosensitive compounds based on bromine-containing 3-acyl-2-furylchromones

Methods have been developed for the synthesis of new photosensitive compounds based on the reaction of N,S,O-nucleophiles with 3-acyl-2-(5-bromofur- 2-yl)chromones and 3-acyl-2-(5-bromomethylfur-2-yl)chromones. The relationship between the spectral proper

Synthesis and reactivity of 1-aryl-9h-thieno[3,4-b]chromon-9-ones

Methods were developed for the synthesis of 1-aryl-9H-thieno[3,4-b]chromon- 9-ones based on the reaction of bromo and dibromo derivatives of 2-methyl-4H-chromon-4-one with thioacetamide in DMF. The thienochromones were modified and their fluorescence prop

Synthesis of 3-alkenyl-2-arylchromones and 2,3-dialkenylchromones via acid-catalysed retro-Michael ring opening of 3-acylchroman-4-ones

3-Acylchromones and 3-acylflavones, readily available by acylation of 2′-hydroxydibenzoylmethane with acid anhydrides in the presence of base, undergo efficient conjugate reduction with NaBH4 in pyridine to give the corresponding chroman-4-ones/flavanones in high yields. The reduction is both regio- and chemoselective. Treatment of the chroman-4-ones with MeSO 3H generates the 3-alkenyl-2-arylchromones by a dehydrative rearrangement initiated by retro-Michael cleavage of the pyranone ring. This reduction-rearrangement sequence can be extended to 2-alkyl-3-alkenoylchromones to generate 3-alkenyl-2-styrylchromones, the first examples of 2,3-dialkenylchromones.