36574-83-1

Basic information

• Product Name: 3,2'-DIHYDROXYCHALCONE
• Synonyms: 1-(2-HYDROXYPHENYL)-3-(3-HYDROXYPHENYL)PROP-2-EN-1-ONE;3,2'-DIHYDROXYCHALCONE;1-(2-Hydroxyphenyl)-3-(3-hydroxyphenyl)-2-propen-1-one;2-Propen-1-one, 1-(2-hydroxyphenyl)-3-(3-hydroxyphenyl)-;Nsc73257
• CAS NO: 36574-83-1
• Molecular Formula: C₁₅H₁₂O₃
• Molecular Weight: 240.25
• Product Categories: Chalcones
• Mol File: 36574-83-1.mol

Chemical Properties

• Boiling Point: 466.2°Cat760mmHg
• Flash Point: 249.9°C
• Appearance: /
• Density: 1.286g/cm³
• Vapor Pressure: 2.58E-09mmHg at 25°C
• Refractive Index: 1.684
• CAS DataBase Reference: 3,2'-DIHYDROXYCHALCONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,2'-DIHYDROXYCHALCONE(36574-83-1)
• EPA Substance Registry System: 3,2'-DIHYDROXYCHALCONE(36574-83-1)

Safety Data

• Hazardous Substances Data: 36574-83-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
3,2'-Dihydroxychalcone is used as a therapeutic agent for its potential to inhibit the growth of cancer cells and modulate the immune response. Its antioxidant and anti-inflammatory properties also contribute to its potential use in treating various health conditions.
Used in Cosmetic Applications:
3,2'-Dihydroxychalcone is used as an ingredient in cosmetic products due to its diverse biological activities, including its antioxidant and anti-inflammatory properties. Its potential to regulate insulin secretion and glucose metabolism also makes it a promising ingredient for products targeting skin health and diabetes-related skin conditions.
Used in Anticancer Applications:
3,2'-Dihydroxychalcone is used as an anticancer agent for its ability to inhibit the growth of cancer cells. Its potential to modulate the immune response may also contribute to its effectiveness in cancer treatment.
Used in Antioxidant and Anti-inflammatory Applications:
3,2'-Dihydroxychalcone is used as an antioxidant and anti-inflammatory agent for its potential to protect cells from oxidative stress and reduce inflammation. This makes it a promising candidate for the development of treatments for various inflammatory and oxidative stress-related conditions.
Used in Antidiabetic Applications:
3,2'-Dihydroxychalcone is used as an antidiabetic agent for its potential to regulate insulin secretion and glucose metabolism. This may contribute to the development of treatments for diabetes and related complications.

InChI:InChI=1/C15H12O3/c16-12-5-3-4-11(10-12)8-9-15(18)13-6-1-2-7-14(13)17/h1-10,16-17H/b9-8+

Upstream product

• 100-83-4 meta-hydroxybenzaldehyde 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 70201-54-6 1-(2-(1-methylethoxy)phenyl)ethanone 
• 118-93-4 o-hydroxyacetophenone 

Downstream Products

• 75848-97-4 2',3-dihydroxy-αβ-dihydrochalcone 
• 70460-18-3 3'-hydroxyflavone 
• 14919-49-4 3-hydroxy-2-(4-hydroxy-phenyl)-chromen-4-one 
• 1386980-99-9 3-(4-oxochroman-2-yl)phenyl phenylcarbamate 
• 92496-65-6 3'-Hydroxyflavanone 
• 1428324-92-8 1-(3-(2-hydroxyphenyl)-5-(3-hydroxyphenyl)-4,5-dihydro-1Hpyrazol-1-yl) ethan-1-one 
• 1362510-67-5 2-[4-(3-hydroxyphenyl)-6-phenylpyridin-2-yl]phenol 
• 75849-01-3 3-(3-benzyloxyphenyl)-1-(2-hydroxyphenyl)propan-1-ol 
• 75849-00-2 2'-hydroxy-3-benzyloxy-αβ-dihydrochalcone 

Relevant articles and documents

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.

Natural product-based design, synthesis and biological evaluation of 2′,3,4,4′-tetrahydrochalcone analogues as antivitiligo agents

A bioactive component, 2′,3,4,4′-tetrahydrochalcone (RY3-a) was first isolated from Vernohia anthelmintica (L.) willd seeds, and a set of its analogs, RY3-a-1–RY3-a-15 and RY3-c were designed and synthesized. Biological activity assays showed that RY3-c exhibited better melanogenesis and antioxidant activity and lower toxicity in comparison with RY3-a and butin. Further study tests showed that RY3-c exhibited better melanogenesis activity compared with the positive control 8-methoxypsoralan (8-MOP) in a vitiligo mouse model, suggesting that RY3-c is a good candidate antivitiligo agent. Mechanistic studies showed that RY3-c could repair cell damage induced by excessive oxidative stress and may exert melanin synthesis activity in the mouse melanoma B16F10 cell line by activating the mitogen-activated protein kinase (MAPK) pathway and the upregulation of c-kit.

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

Design, synthesis and MAO inhibitory activity of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives

A series of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives (aurones, 1–20) were synthesized and screened for their inhibitory activity against hMAO. Seventeen compounds (1–5, 7–17, 19) were found to be selective towards hMAO-B, while two w

QSAR, in silico docking and in vitro evaluation of chalcone derivatives as potential inhibitors for H1N1 virus neuraminidase

Thirty three chalcones were synthesized and tested on viral H1N1 neuraminidase activity by using MUNANA assay [2′-(4-methylumbelliferyl)-α-d-N-acetylneuraminic acid] assay with DANA (2,3-didehydro-2-deoxy-N-acetylneuraminic acid) was used as standard. 2D and 3D-quantitative structure?activity relationship models have been successfully developed with a good correlative and predictive ability for quantitative structure?activity relationships of these chalcone derivatives. Result from the 2D-quantitative structure?activity relationship model indicates that electrostatic parameter enhanced bioactivity of the chalcones while steric substituents diminished their potency as H1N1 neuraminidase inhibitors. 3D-quantitative structure?activity relationship model showed the importance of the position of the hydroxyl group in chalcone derivatives which can influence on hydrophobicity, hydrogen bond donor and aromatic ring features that enhance the biological activity. Finally, docking studies showed that chalcones MC8 and MC16 with low C docker interaction energies and higher numbers of hydrogen bonding have better inhibitory activity against viral H1N1 neuraminidase.

Synthesis and antiviral activity of 2-aryl-4H-chromen-4-one derivatives against Chikungunya virus

A series of nineteen 2-aryl-4H-chromen-4-one derivatives 2a-2s were synthesized and evaluated for their antiviral activity against Chikungunya virus (LR2006-OPY1) in Vero cell culture by CPE reduction assay. Three compounds 2a, 2b and 2g, were found to be active at concentration of (IC50) 0.44 μM, 0.45 μM and 2.02 μM, respectively. Compounds having heterocyclic ring 2a and 2b at the 2nd position of the chromenone were found to be potent inhibitor of ChikV. Cytotoxicity studies were performed using Vero cell culture, compounds 2a and 2b exhibited SI of ≥100. Molecular docking simulation has been carried out to understand the possible mechanism of action.

Monoamine oxidase inhibitory activity of 2-aryl-4H-chromen-4-ones

A series of twenty 2-aryl-4H-chromen-4-one (flavones) derivatives (3a-3s) were synthesized and tested for hMAO inhibitory activity. Fifteen compounds (3a, 3c, 3e-3h, 3j-3p, 3r, 3s) were found to be selective towards MAO-B, while 3d was selective towards MAO-A, and 3b, 3i and 3q were non-selective. Experimental Selectivity Index for MAO-B ranges from 2.0 (3g, 3p) to 30.0 (3j). Compound 3j, which is carrying 3,4-di-OMeC6H3 groups at R position on the molecule, was found to be potent MAO-B inhibitor amongst the fifteen with Ki value for MAO-B of 0.16 ± 0.01 lM comparable to that of standard drug, Selegiline (Ki for MAO-B is 0.16 ± 0.01 μM). Compound 3j also appeared as the most selective MAO-B inhibitor according to its best selectivity index (30.0), which is comparable to that of Selegiline (SIMAO-B = 35.0). Molecular docking and molecular dynamics simulation studies were carried out using Autodock-4.0 and Amber12 to understand the molecular level interaction and energy relation of MAO isoforms with selective inhibitors (3d and 3j). Simulation results are in good agreement with the experimental results. Leads identified may further be explored to develop potent isoform specific inhibitors of MAO.

Synthesis and biological activity of 2,4-di-p-phenolyl-6-2-furanyl-pyridine as a potent topoisomerase II poison

Dihydroxylated 2,4-diphenyl-6-aryl pyridine derivatives were simply achieved using Claisen-Schmidt condensation reaction and modified Kr?hnke pyridine synthetic method. Total forty-five compounds were designed and synthesized which contain hydroxyl groups

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Dihydroxylated 2,4-diphenyl-6-aryl pyridine derivatives were simply achieved using Claisen-Schmidt condensation reaction and modified Kr?hnke pyridine synthetic method. Total forty-five compounds were designed and synthesized which contain hydroxyl groups

Nanosilica-supported dual acidic ionic liquid as a heterogeneous and reusable catalyst for the synthesis of flavanones under solvent-free conditions

[Figure not available: see fulltext.] A nanosilica-supported dual acidic ionic liquid on the basis of 1-methyl-3-(4-sulfobutyl)imidazolium hydrogen sulfate was synthesized and used as an efficient, green, non-corrosive, non-toxic, heterogeneous, and reusable catalyst for the synthesis of some new and known substituted flavanones. The synthesis was done by the condensation of 2'-hydroxyacetophenone with different aldehydes and the subsequent cyclization of the resulting 2'-hydroxychalcone in the presence of the catalyst. High yields of the products, short reaction times, and solvent-free conditions characterize this new method.