55947-36-9

Basic information

• Product Name: 5-METHOXYFLAVANONE
• Synonyms: METHOXYFLAVANONE, 5-;5-METHOXYFLAVANONE;METHOXYFLAVANONE, 5-(P);2,3-Dihydro-5-methoxy-2-phenyl-4H-1-benzopyran-4-one;2-Phenyl-5-methoxychroman-4-one;5-methoxy-2-phenyl-2,3-dihydrochromen-4-one;5-methoxy-2-phenyl-chroman-4-one
• CAS NO: 55947-36-9
• Molecular Formula: C₁₆H₁₄O₃
• Molecular Weight: 254.28
• Product Categories: Flavanones;Benzopyrans;Building Blocks;Heterocyclic Building Blocks
• Mol File: 55947-36-9.mol

Chemical Properties

• Melting Point: 144-145°C
• Boiling Point: 436.1°C at 760 mmHg
• Flash Point: 209.4°C
• Appearance: /
• Density: 1.199g/cm³
• Vapor Pressure: 8.28E-08mmHg at 25°C
• Refractive Index: 1.587
• CAS DataBase Reference: 5-METHOXYFLAVANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHOXYFLAVANONE(55947-36-9)
• EPA Substance Registry System: 5-METHOXYFLAVANONE(55947-36-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 55947-36-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Methoxyflavanone is used as a therapeutic agent for its antioxidant properties, serving to combat oxidative stress and inflammation-related diseases. Its anti-inflammatory effects make it a potential candidate for treating conditions where inflammation is a contributing factor.
Used in Cancer Treatment:
In the field of oncology, 5-Methoxyflavanone is utilized as an anti-cancer agent, leveraging its potential to mitigate the effects of cancer and support the prevention of oxidative stress that can lead to the development of cancerous cells.
Used in Cardiovascular Health:
5-Methoxyflavanone is used as a cardiovascular health supplement due to its demonstrated ability to regulate cholesterol levels, thereby supporting heart health and potentially reducing the risk of cardiovascular diseases.
Used in Nutraceutical Industry:
As a component of dietary supplements, 5-Methoxyflavanone is used to enhance overall health by providing its antioxidant and anti-inflammatory benefits, contributing to the prevention of various diseases and promoting well-being.
Used in Cosmetic Industry:
Given its antioxidant properties, 5-Methoxyflavanone may also be used in the cosmetic industry to protect the skin from oxidative damage, potentially reducing the signs of aging and promoting skin health.

InChI:InChI=1/C16H14O3/c1-18-13-8-5-9-14-16(13)12(17)10-15(19-14)11-6-3-2-4-7-11/h2-9,15H,10H2,1H3

Upstream product

• 40524-67-2 (E)-1-(2-hydroxy-6-methoxyphenyl)-3-phenylprop-2-en-1-one 
• 703-23-1 2'-hydroxy-6'-methoxyacetophenone 
• 100-52-7 benzaldehyde 
• 42079-78-7 5-methoxyflavone 
• 40524-67-2 2'-Hydroxy-6'-methoxychalcone 
• 6279-84-1 β-(m-methoxyphenoxy)propionitrile 
• 863309-86-8 5-methoxychroman-4-one 
• 98-80-6 phenylboronic acid 
• 150-19-6 O-methylresorcine 

Downstream Products

• 42079-77-6 8-bromo-5-methoxy-2-phenyl-chromen-4-one 
• 40524-67-2 (E)-1-(2-hydroxy-6-methoxyphenyl)-3-phenylprop-2-en-1-one 
• 93012-39-6 6-hydroxy-5-methoxy-2-phenyl-chroman-4-one 
• 92873-06-8 5-methoxy-8-bromo-flavanone 
• 469911-88-4 5-methoxy-6,8-dibromo-flavanone 
• 6665-69-6 3,5-dihydroxy-2-phenyl-4H-chromen-4-one 
• 42079-78-7 5-methoxyflavone 
• 123931-32-8 C₁₆H₁₄O₃ 
• 123931-32-8 C₁₆H₁₄O₃ 

Relevant articles and documents

Synthesis and Investigation of Flavanone Derivatives as Potential New Anti-Inflammatory Agents

Flavonoids are polyphenols with broad known pharmacological properties. A series of 2,3-dihydroflavanone derivatives were thus synthesized and investigated for their anti-inflammatory activities. The target flavanones were prepared through cyclization of 2′-hydroxychalcone derivatives, the later obtained by Claisen–Schmidt condensation. Since nitric oxide (NO) represents an important inflammatory mediator, the effects of various flavanones on the NO production in the LPS-induced RAW 264.7 macrophage were assessed in vitro using the Griess test. The most active compounds were flavanone (4G), 2′-carboxy-5,7-dimethoxy-flavanone (4F), 4′-bromo-5,7-dimethoxy-flavanone (4D), and 2′-carboxyflavanone (4J), with IC50 values of 0.603, 0.906, 1.030, and 1.830 μg/mL, respectively. In comparison, pinocembrin achieved an IC50 value of 203.60 μg/mL. Thus, the derivatives synthesized in this work had a higher NO inhibition capacity compared to pinocembrin, demonstrating the importance of pharmacomodulation to improve the biological potential of natural molecules. SARs suggested that the use of a carboxyl-group in the meta-position of the B-ring increases biological activity, whereas compounds carrying halogen substituents in the para-position were less active. The addition of methoxy-groups in the meta-position of the A-ring somewhat decreased the activity. This study successfully identified new bioactive flavanones as promising candidates for the development of new anti-inflammatory agents.

Convenient synthesis of flavanone derivatives via oxa-Michael addition using catalytic amount of aqueous cesium fluoride

A total of 36 flavanones, which included polycyclic aromatic and heterocyclic rings, were readily synthesized via oxa-Michael addition from the corresponding hydroxychalcones with a catalytic amount of aqueous cesium fluoride solution under mild conditions. This method could be applied to the scalable synthesis of eriodictyol as a known potent inhibitor of the SARS-CoV-2 spike protein.

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.

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.

Highly efficient and green synthesis of flavanones and tetrahydroquinolones

Highly efficient and green catalytic conversion of 2′-hydroxy and 2′-amino chalcones to flavanones and tetrahydroquinolones is reported herein. 2′-Hydroxy and 2′-amino chalcones can be almost completely converted to flavanones and tetrahydroquinolones in just 2 min in the presence of piperidine and KOH under room temperature. Liquiritigenin is also efficiently synthesized under similar conditions.

Microbial metabolism. Part 10: Metabolites of 7,8-dimethoxyflavone and 5-methoxyflavone

Microbial transformation of 7,8-dimethoxyflavone (1) by Mucor ramannianus produced five metabolites: 7,8-dimethoxy-4′-hydroxyflavone (2), 3′,4′-dihydroxy-7,8-dimethoxyflavone (3), 7,3′-dihydroxy-8- methoxyflavone (4), 7,4′-dihydroxy-8-methoxyflavone (5) a

CONVERSION OF 2'-HYDROXYCHALCONES TO FLAVANONES CATALYZED BY COBALT SHIFF BASE COMPLEX

Co(salpr) catalyzes the conversion of 2'-hydroxychalcones to flavanones in methanol under oxygen.Base catalysis by Co(salpr) (OH) produced in situ is responsible for the reaction, which is found to proceed reversibly.

Kinetics and Mechanism of the Cyclisation of 2',6'-Dihydroxychalcone and Derivates

pH-Rate profiles are reported for the cyclisation in water to 5-hydroxyflavanones of 2',6'-dihydroxychalcone (1) and its 4-methoxy (2), 3,4-dimethoxy (3), 3,4,5-trimethoxy (4), 2,4,6-trimethoxy (5), 4-chloro (6), and 3,4,4'-trimethoxy (8) derivates.As for the previously studied 2',6'-dihydroxy-4,4'-dimethoxychalcone (7), rate coefficients are established for acid-catalysed cyclisation of neutral chalcone, for unimolecular cyclisation of the neutral, monoanionic, and dianionic chalcone, and for the base-catalysed reverse ring-opening reaction.Cyclisation of the monoanion of 2',6'-dihydroxychalcone is almost 40 times faster than that of the monoanion of the 2'-hydroxy-6'-methoxyhalcone (10) and is also estimated to be about ten times faster than that of the reactive monoanion of 2',4'-dihydroxychalcone.These are the first calculations of the enhancement of rate of monoanion cyclisation by the 6'-OH group.The effect is only small, and is suggested to arise largely from stabilisation of the transition state for ketonisation by hydrogen bonding to enolate oxygen.Other reactivity differences amongst the chalcone monoanions are also discussed.Enthalpy and entropy of activation data are reported for monoanion cyclisation of (1), (2), and (4)-(6).Rate coefficients for the cyclisation of the chalcone monoanions are almost identical for (1)-(4) and (6) in water but not in deuterium oxide: kinetic hydrogen isotope effect (KIE) values are 3.4 (1), 5.7 (2), 4.9 (3), 3.0 (4), 7.5 (5), 2.9 (6), and 5.0 (8).For chalcones (2) and (7), the KIE values of which are both 5.7, the amounts of H versus D incorporation at the flavanone 3-carbon for monoanion cyclisation in H2O/D2O mixtures were established by mass spectroscopy.This gave product (or 'discrimination') isotope effect (PIE) values of 7.9 for (2) and 3.8 for (7), suggesting for (2) but not (7) an inverse effect contribution to KIE from sources other than rate-limiting proton transfer to carbon.Monoanion cyclisation of (1) in D2O was established by 1H n.m.r. as involving almost equal amounts of anti and syn addition of 2'-O- to the enone double bond.Reactivity differences amongst the chalcones for reactions other than monoanion cyclisation are only briefly considered.

The Kinetics and Mechanism of the Cyclisation of Some 2'-Hydroxychalcones to Flavanones in Basic Aqueous Solution

Rate coefficients for the chalcone-flavanone equilibration reaction have been established for some 2'-hydroxychalcones over the pH range (ca. 8-11) in which their 2'-hydroxy-groups undergo ionisation.The chalcones studied were the parent 2'-hydroxychalcone (I) and its following derivatives: 4'-OMe (II), 6'-OMe (III), 4'-OH (IV), 4',6'-Me2 (V), and 5',6'-benzo (VI).Pseudo-first-order rate coefficients (kobs) which, for the reversible reactions concerned, are the sum of the forward and reverse rate coefficients, were fitted to the kinetic form, kobs=kfA+k'fB+k''aOH- in which k and k' are the rate coefficients for the unimolecular cyclisation of neutral and of ionised chalcones respectively (fA and fB are the fractions of total chalcone present in the neutral and ionised forms at the pH concerned) and where k'' is the second-order rate coefficient for the reverse reaction of flavanone which involves hydroxide ion (activity aOH-).Data analysis gave rate coefficients and pKa values for all but chalcone (IV) which has a different kinetic form.A conjugate addition-elimination mechanism is proposed to account for the pH-rate profiles, one of which differs from that previously reported.Possible effects on rate coefficients of non-bonded interactions between 6'-substituents and carbonyl oxygen are briefly considered but the differences between chalcones with and without 6'-substituents are sufficiently small to deter prolonged discussion.There seems to be little serious hindrance of cyclisation for any of the 6'-substituted chalcone anions.