15131-80-3

Basic information

• Product Name: 2,2'-DIHYDROXYCHALCONE
• Synonyms: 1,3-bis(2-hydroxyphenyl)-2-propen-1-on;1,3-bis(2-hydroxyphenyl)-2-propen-1-one;2’-hydroxy-3-(o-hydroxyphenyl)-acrylophenon;2,2'-DIHYDROXYCHALCONE;1,3-DI(2-HYDROXYPHENYL)PROP-2-EN-1-ONE;2,2''-DIHYDROXYCHALCHONE;2-Propen-1-one, 1,3-bis(2-hydroxyphenyl)-;Acrylophenone, 2'-hydroxy-3-(o-hydroxyphenyl)-
• CAS NO: 15131-80-3
• Molecular Formula: C₁₅H₁₂O₃
• Molecular Weight: 240.25
• Product Categories: Chalcones
• Mol File: 15131-80-3.mol

Chemical Properties

• Melting Point: 161-162°C
• Boiling Point: 447.1 °C at 760 mmHg
• Flash Point: 238.3 °C
• Appearance: /
• Density: 1.286 g/cm³
• PKA: 7.72±0.30(Predicted)
• CAS DataBase Reference: 2,2'-DIHYDROXYCHALCONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-DIHYDROXYCHALCONE(15131-80-3)
• EPA Substance Registry System: 2,2'-DIHYDROXYCHALCONE(15131-80-3)

Safety Data

• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 15131-80-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,2'-DIHYDROXYCHALCONE is used as a therapeutic agent for its potential role in the treatment of various diseases and conditions, such as cancer, diabetes, and neurodegenerative disorders. Its antioxidant, anti-inflammatory, and anticancer properties make it a valuable compound for developing new drugs and treatment strategies.
Used in Food Industry:
2,2'-DIHYDROXYCHALCONE is used as a natural antioxidant in the food industry to extend the shelf life of products and maintain their quality. Its antioxidant properties help prevent the oxidation of fats and oils, thus preserving the nutritional value and sensory attributes of food products.
Used in Cosmetic Industry:
2,2'-DIHYDROXYCHALCONE is used as an ingredient in cosmetic products for its antioxidant properties. It can help protect the skin from oxidative stress and environmental damage, promoting skin health and preventing premature aging.
Used in Research and Development:
2,2'-DIHYDROXYCHALCONE is used as a subject of research for its potential benefits and mechanisms of action. Further studies are needed to fully understand its therapeutic potential and explore new applications in various fields, such as medicine, food, and cosmetics.

Upstream product

• 118-93-4 o-hydroxyacetophenone 
• 90-02-8 salicylaldehyde 
• 89-95-2 2-methyl-benzyl alcohol 
• 1006623-69-3 2′-hydroxyflavylium tetrafluoroborate 
• 31165-67-0 2'-benzyloxyacetophenone 
• 5896-17-3 2-(phenylmethoxy)benzaldehyde 
• 5533-04-0 2-(methoxymethoxy)benzaldehyde 

Downstream Products

• 1058163-32-8 C₂₁H₁₇NO₂S 
• 55370-67-7 3,5-bis-(2-hydroxyphenyl)-4,5-dihydro-1H-pyrazole 
• 35244-11-2 2'-hydroxyflavone 
• 74599-69-2 3-(2-Hydroxybenzyl)-chroman-4-on 
• 6068-76-4 3,2'-dihydroxyflavone 
• 1386980-98-8 2-(4-oxochroman-2-yl)phenyl phenylcarbamate 
• 17348-76-4 2'-hydroxyflavanone 

Relevant articles and documents

Hydroxychalcone dyes that serve as color indicators for pH and fluoride ions

A chalcone, which is composed of two aromatic rings bridged by an α,β-unsaturated carbonyl group, exhibits a variety of biological activities. With an objective to develop a novel chalcone-based functional dye, we have synthesized a chalcone diol CLN1, bearing two OH groups at the 2-positions on both phenyl rings, as well as reference compounds CLN2-6, and found that it serves as color indicators for pH and fluoride ions. CLN1showed a vivid color change from colorless to yellow (halochromism) in water at pH ≥ 10. Furthermore, it presented a selective color change from colorless to red upon the addition of TBAF in an organic solvent such as CH3CN. CLN1provided a strong red-shifted absorption band in the visible region under alkaline conditions in water and upon the addition of TBAF in CH3CN. The absorption spectral study together with TD-DFT calculations and X-ray crystallographic analysis revealed that the characteristic π-resonant structures of CLN1caused by the ionization or OH-F?interactions and the planar conformation due to its intramolecular hydrogen bonding may provide a strong charge transfer (CT) absorption in the visible region.

2′-Hydroxyflavylium: introducing flavanones into the flavylium network of chemical reactions

Chalcones possessing a hydroxyl group in position 2 cyclize to form flavylium salts in acidic media, this reaction being reversible under neutral-basic conditions. On the other hand, chalcones possessing a hydroxyl group in position 2′ cyclize to form flavanones in basic media. By synthesizing 2′-hydroxyflavylium tetrafluoroborate, it was possible to obtain trans-2,2′-dihydroxychalcone that in solution can evolve to 2′-hydroxyflavanone or back to 2′-hydroxyflavylium depending on the pH. The several equilibria established in aqueous solution were fully characterized. The importance of including flavanones into the flavylium network of chemical reactions is briefly exploited.

Effect of OH substitution in 3-benzylchroman-4-ones: crystallographic, CSD, DFT, FTIR, Hirshfeld surface, and energy framework analysis

3-Benzylchroman-4-ones (homoisoflavanones) are oxygen-containing heterocycles with a sixteen-carbon skeleton. They belong to the class of naturally occurring polyphenolic flavonoids with limited occurrence in nature and possess anti-inflammatory, antibact

Mycobactin Analogues with Excellent Pharmacokinetic Profile Demonstrate Potent Antitubercular Specific Activity and Exceptional Efflux Pump Inhibition

In this study, we have designed and synthesized pyrazoline analogues that partially mimic the structure of mycobactin, to address the requirement of novel therapeutics to tackle the emerging global challenge of antimicrobial resistance (AMR). Our investigation resulted in the identification of novel lead compounds 44 and 49 as potential mycobactin biosynthesis inhibitors against mycobacteria. Moreover, candidates efficiently eradicated intracellularly surviving mycobacteria. Thermofluorimetric analysis and molecular dynamics simulations suggested that compounds 44 and 49 bind to salicyl-AMP ligase (MbtA), a key enzyme in the mycobactin biosynthetic pathway. To the best of our knowledge, these are the first rationally designed mycobactin inhibitors to demonstrate an excellent in vivo pharmacokinetic profile. In addition, these compounds also exhibited more potent whole-cell efflux pump inhibition than known efflux pump inhibitors verapamil and chlorpromazine. Results from this study pave the way for the development of 3-(2-hydroxyphenyl)-5-(aryl)-pyrazolines as a new weapon against superbug-associated AMR challenges.

Differences in antioxidant potential of chalcones in human serum: In vitro study

Introduction: An imbalance between oxidants and antioxidants in favour of oxidants, potentially leading to damage, is termed oxidative stress. Antioxidants (AO), either enzymatic or non-enzymatic, are the ones that can reduce diverse effects of pro-oxidan

Novel isoniazid-spirooxindole derivatives: design, synthesis, biological evaluation, in silico ADMET prediction and computational studies

In the present scenario, the Synthesis of new and desired antimycobacterial agent has an eternal demand to resist Mycobacterium tuberculosis (MTB). The design and identification of new molecules for the treatment of tuberculosis is an important task in organic as well as medicinal chemistry research. In the present study, we have reported the combination of the desired compound using two versatile and significant moieties, isoniazid and spirooxindole derivatives. A series of novel isoniazid-spirooxindole hybrid molecules (6a-6ao) were designed, synthesized, and well-characterized by various spectroscopic methods. We have evaluated for their in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (MTB) strain and MDR-TB. Among them, Compound 6ab was found to be the most effective compare to other compounds. ADMET-related descriptors were to be calculated of all the compounds to predict the pharmacokinetic properties for the selection of the effective and bioavailable compounds. In addition, molecular docking and molecular dynamics studies reveal that the binding modes of all the compounds in the active site of isoniazid-resistant enoyl-ACP(COA) reductase, which helped to establish a structural basis of inhibition of Mycobacterium tuberculosis.

Synthesis, Structure, and Anti-Inflammatory Activity of Functionally Substituted Chalcones and Their Derivatives

Functionally substituted chalcones, pyrazolines, and flavonones have been synthesized. Their structure has been studied by means of 1H and 13C NMR spectroscopy, including COSY and HMQC experiments. Anti-inflammatory activity of the s

Synthesis, in vitro antigiardial activity, SAR analysis and docking study of substituted chalcones

A series of 15 chalcones-bearing substituents at positions 2, 4, and 5 of rings A and B were synthesized using microwave-assisted Claissen–Smichdt condensation and evaluated for their activity against Giardia lamblia and Green monkey kidney cells. Five co

Phototransformations of some 3-cyclohexenyloxychromenones: Synthesis of Spirocyclic compounds

The phototransformation of the 3-cyclohexenyloxychromenones by irradiation with a pyrex-filtered light from a 125 W Hg vapor lamp under an inert atmosphere into the spirocyclic fused xanthenones was described. The efficacy of the protocol depended upon th

Metal-free Synthesis of Spiro-2,2′-benzo[b]furan-3,3′-ones via PhI(OAc)2-Mediated Cascade Spirocyclization

Treating the benzyl protected 3-hydroxy-1,3-bis(2-hydroxyphenyl)prop-2-en-1-ones solely with PhI(OAc)2 (PIDA) in DCE at room temperature readily furnished the seldom studied spiro-2,2′-benzo[b]furan-3,3′-ones in satisfactory to excellent yields. The hypervalent iodine reagent enables the metal-free cascade spirocyclization resulting in the dual oxidative C?O bond formation. (Figure presented.).