2545-13-3

Usage

Uses

Used in Health and Wellness Applications:
(-)-7-hydroxyflavanone is used as a natural antioxidant and anti-inflammatory agent for reducing inflammation and oxidative stress in the body, which may contribute to overall health and wellness.
Used in Cardiovascular Health:
(-)-7-hydroxyflavanone is used as a supportive compound for cardiovascular health, potentially aiding in the maintenance and improvement of heart function.
Used in Anticancer Applications:
(-)-7-hydroxyflavanone is used as a compound with potential anti-cancer properties, showing promise in the prevention and treatment of cancer.
Used in Dermatology:
(-)-7-hydroxyflavanone is used as a potential skincare ingredient in dermatology, leveraging its antioxidant and anti-inflammatory properties to improve skin health and appearance.

Upstream product

• 21785-09-1 7-methoxyflavanone 
• 3144-16-9 (1S)-10-camphorsulfonic acid 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 100-52-7 benzaldehyde 
• 59887-89-7 7-hydroxy-4H-chromen-4-one 
• 98-80-6 phenylboronic acid 
• 6515-36-2 7-hydroxy-2-phenyl-chroman-4-one 
• 76240-27-2 7-hydroxy-2,3-dihydro-4H-chromen-4-one 
• 76240-23-8 3-(3-Hydroxyphenoxy)propanenitrile 
• 102-92-1 Cinnamoyl chloride 
• 140-10-3 (E)-3-phenylacrylic acid 
• 126686-33-7 7-Methoxymethoxy-2-phenyl-chroman-4-one 
• 108-46-3 recorcinol 
• 133360-49-3 3-<2,4-di(t-butyldimethylsilyloxy)phenyl>-5-phenylisoxazoline 

Downstream Products

• 94829-91-1 4-oxo-2-phenylchroman-7-yl acetate 
• 53258-99-4 7-hydroxy-8-(3-methylbut-2-en-1-yl)-2-phenylchroman-4-one 
• 78045-71-3 7-(γ,γ-dimethylallyloxy)flavanone 
• 866141-85-7 7-hydroxy-6-C-prenylflavanone 
• 59920-27-3 7-hydroxy-6,8-di-C-prenylflavanone 
• 89840-30-2 7-(2,3-trans-3,4-cis-3-hydroxyflavan-4-yloxy)flavanone 
• 1776-30-3 (E)-2',4'-dihydroxychalcone 
• 67832-08-0 (+/-)-5,7-Dihydroxy-6-(1''-geranyl)flavanone 
• 136397-09-6 C₁₈H₁₆O₄ 
• 1450913-55-9 1-(3-chlorophenyl)-3-(2-(2-hydroxy-3-(4-oxo-2-phenylchroman-7-yloxy)propylamino)ethyl)urea 
• 82416-18-0 2',4'-diacetoxychalcone 

Relevant academic research and scientific papers

Asymmetric Synthesis of Sakuranetin-Relevant Flavanones for the Identification of New Chiral Antifungal Leads

Discovery and efficient synthesis of new promising leads have a central role in agrochemical science. Reported herein is the sakuranetin-directed synergistic exploration of an asymmetric synthesis and an antifungal evaluation of chiral flavanones. A new palladium catalytic system with CarOx-type ligands was successfully identified for the highly enantioselective addition of arylboronic acids to chromones. This enabled the facile and programmable construction of a constellation of chiral flavanones (up to 98% yield and 97% ee), in which (R)-pinostrobin was efficiently constructed without laborious protecting/deprotecting operations. Its good performance in asymmetric induction and functional tolerance expanded the chemical space of pharmaceutically important flavanones. The chiral differentiation of flavanones based on antifungal activity and a concise structure-activity relationship model was disclosed and summarized. This synergistic project culminated with acquisition of the naturally unprecedented flavanones with better antifungal potentials than sakuranetin, in which the R-enantiomer of flavanone 54 (EC50 = 0.8 μM) demonstrated better performance than boscalid against Rhizoctonia solani. The novel scaffold and predicted new target compared with the commercial fungicides in the FRAC reinforce the value of further exploration.

Design, synthesis, and cholinesterase inhibition assay of liquiritigenin derivatives as anti-Alzheimer's activity

The marine environment is a rich resource for discovering functional materials, and seaweed is recognized for its potential use in biology and medicine. Liquiritigenin has been isolated and identified from Sargassum pallidum. To find new anti-Alzheimer's activity, we designed and synthesized thirty-two 7-prenyloxy-2,3-dihydroflavanone derivatives (3a-3p) and 5-hydroxy-7-prenyloxy-2,3-dihydro-flavanone derivatives (4a-4p) as cholinesterases inhibitors based on liquiritigenin as the lead compound. Inhibition screening against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) indicated that all synthesized compounds possessed potent AChE inhibitory activity and moderated to weak BuChE inhibitory activity in vitro. Kinetic studies demonstrated that compound 4o inhibited AChE via a dual binding site ability. In addition, all compounds displayed the radical scavenging effects. Finally, the molecular docking simulation of 4o in AChE active site displayed good agreement with the obtained the pharmacological results.

Total Synthesis of Caesalpinnone A and Caesalpinflavan B: Evolution of a Concise Strategy

The total syntheses of caesalpinnone A (1) and its putative biosynthetic precursor caesalpinflavan B (3) are described. Herein, we describe the evolution of a synthetic strategy toward 1 and 3, which entails a convergent Barluenga coupling that quickly delivers a heavily functionalized benzopyran containing the core carbon framework and exploration of two distinct synthetic routes for forging the flavanoid C-ring by reducing a sterically encumbered embedded alkene: one via a stepwise approach and a second, more direct and atom-economical, enabled by a Shenvi-HAT hydrogenation. The latter strategy allowed access to caesalpinflavan B in 6 steps after Pd-mediated deallylation. A late-stage dearomative phenolic oxidation and deallylation/oxa-Michael cascade was implemented to access caesalpinnone A (1) in 7 steps. We also describe an enantioselective total synthesis and stereochemical revision of (-)-caesalpinflavan B, as well as a formal enantioselective synthesis of (-)-caesalpinnone A, by implementing an enantioselective Pd-catalyzed conjugate addition developed by Stoltz.

Synthesis of Flavanones via Palladium(II)-Catalyzed One-Pot β-Arylation of Chromanones with Arylboronic Acids

A total of 47 flavanones were expediently synthesized via one-pot β-arylation of chromanones, a class of simple ketones possessing chemically unactivated β sites, with arylboronic acids via tandem palladium(II) catalysis. This reaction provides a novel route to various flavanones, including natural products such as naringenin trimethyl ether, in yields up to 92percent.

Enantioselective potential of polysaccharide-based chiral stationary phases in supercritical fluid chromatography

The enantioselective potential of two polysaccharide-based chiral stationary phases for analysis of chiral structurally diverse biologically active compounds was evaluated in supercritical fluid chromatography using a set of 52 analytes. The chiral selectors immobilized on 2.5?μm silica particles were tris-(3,5-dimethylphenylcarmabate) derivatives of cellulose or amylose. The influence of the polysaccharide backbone, different organic modifiers, and different mobile phase additives on retention and enantioseparation was monitored. Conditions for fast baseline enantioseparation were found for the majority of the compounds. The success rate of baseline and partial enantioseparation with cellulose-based chiral stationary phase was 51.9% and 15.4%, respectively. Using amylose-based chiral stationary phase we obtained 76.9% of baseline enantioseparations and 9.6% of partial enantioseparations of the tested compounds. The best results on cellulose-based chiral stationary phase were achieved particularly with propane-2-ol and a mixture of isopropylamine and trifluoroacetic acid as organic modifier and additive to CO2, respectively. Methanol and basic additive isopropylamine were preferred on amylose-based chiral stationary phase. The complementary enantioselectivity of the cellulose- and amylose-based chiral stationary phases allows separation of the majority of the tested structurally different compounds. Separation systems were found to be directly applicable for analyses of biologically active compounds of interest.

Functionalities tuned enantioselectivity of phenylcarbamate cyclodextrin clicked chiral stationary phases in HPLC

The mixed chloro- and methyl- functionalities can greatly modulate the enantioselectivities of phenylcarbamate cyclodextrin (CD) clicked chiral stationary phases (CSPs). A comparison study is herein reported for per(4-chloro-3-methyl)phenylcarbamate and per(2-chloro-5-methyl)phenylcarbamate β-CD clicked CSPs (i.e., CCC4M3-CSP and CCC2M5-CSP). The enantioselectivity dependence on column temperature was studied in both normal-phase and reversed-phase mode high performance liquid chromatography (HPLC). The thermodynamic study revealed that the stronger intermolecular interactions can be formed between CCC4M3-CSP and chiral solutes to drive the chiral separation. The higher enantioselectivities of CCC4M3-CSP were further demonstrated with the enantioseparation of 17 model racemates in HPLC.

Fast and efficient synthesis of flavanones from cinnamic acids

A fast and efficient synthesis of flavanones from cinnamic acids in three steps has been developed. First, the cinnamic acid was converted to cinnamyol chlorides using SOCl2. The acid chlorides were then treated with substituted phenols in BF3· OEt2to furnish corresponding chalcones in 42(75% yields. Base-catalyzed cyclization of the chalcones at room temperature afforded corresponding flavones in 85–95% yields. The conversion of the cinnamic acid derivatives to corresponding chalcones was found to be sensitive to the position and nature of the substituents on the aromatic rings.

Efficient HPLC enantiomer separation using a pillared homochiral metal-organic framework as a novel chiral stationary phase

HPLC enantioseparation of racemates using novel pillared homochiral metal-organic framework-silica composite as chiral stationary phase has been successfully demonstrated.

Design, Synthesis, and Potential Antidepressant-like Activity of 7-prenyloxy-2,3-dihydroflavanone Derivatives

A series of 7-prenyloxy-2, 3-dihydroflavanone derivatives were synthesized and screened for their antidepressant-like activity. Among them, it was observed that compounds 5j and 5k were found to be the most antidepressant-like activity. In addition, it was found that compounds 5j and 5k significantly increased the concentrations of the main neurotransmitters 5-HT and NE in the hippocampus, hypothalamus, and cortex. Compounds 5j and 5k also significantly increased the contents of 5-HIAA in the hippocampus and cortex, shut down 5-HT metabolism compared with mice treated with stress vehicle. These results suggested that compounds 5j and 5k displayed potent antidepressant-like properties that were mediated via neurochemical systems.

Synthesis of flavanones using methane sulphonic acid as a greencatalystand comparision under different conditions

Flavonoids are an important class of natural products with wide range activities. Flavonoids includes flavone, flavanone, flavane & flavanol. The synthetic route invovles synthesis of chalcone followed by ring closing to give flavanone. So many catalysts were mentioned in past literature. But most efficient catalyst is methane sulphonic acid.It is easy to handle,less reaction time &easily available. Flavanones were synthesized from chalcone using methane sulphonic acid under thermal condition, microw wave and ultrasound condition.Flavanones are syntheisized in very less time compared to other conditions.