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
• Article Data: 9

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

General Description

5-Methoxyflavanone is a natural compound belonging to the flavanone class of flavonoids. It is characterized by a methoxy group attached to the 5-carbon of the flavanone backbone. This chemical is commonly found in various plant sources, including citrus fruits and their peels. 5-Methoxyflavanone has been reported to exhibit potential biological activities, including antioxidant, anti-inflammatory, and anti-cancer properties. It has also been studied for its potential role in preventing oxidative stress and inflammation-related diseases. Additionally, 5-methoxyflavanone has shown promise in regulating cholesterol levels and supporting cardiovascular health. These findings suggest that this compound may have potential therapeutic applications in the management of various health conditions.

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 
• 150-19-6 O-methylresorcine 
• 863309-86-8 5-methoxychroman-4-one 
• 98-80-6 phenylboronic acid 
• 6279-84-1 β-(m-methoxyphenoxy)propionitrile 
• 40524-67-2 2'-Hydroxy-6'-methoxychalcone 
• 42079-78-7 5-methoxyflavone 

Downstream Products

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

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.

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.

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.