1036-72-2

Basic information

• Product Name: 5,7-DIMETHOXYFLAVANONE
• Synonyms: DIMETHOXYFLAVANONE,5,7-;5,7-DIMETHOXYFLAVANONE;PINOCEMBRIN DIMETHYL ETHER;5,7-DIMETHOXYFLAVANONE 97%;2,3-Dihydro-5,7-dimethoxy-2-phenyl-4H-1-benzopyran-4-one;2-Phenyl-5,7-dimethoxy-2,3-dihydro-4H-1-benzopyran-4-one;5,7-Dimethylpinocembrin;5,7-dimethoxy-2-phenyl-2,3-dihydrochromen-4-one
• CAS NO: 1036-72-2
• Molecular Formula: C₁₇H₁₆O₄
• Molecular Weight: 284.31
• Mol File: 1036-72-2.mol
• Article Data: 18

Chemical Properties

• Melting Point: 144-146°C
• Boiling Point: 468.8°Cat760mmHg
• Flash Point: 209.4°C
• Appearance: /
• Density: 1.204g/cm³
• Vapor Pressure: 5.79E-09mmHg at 25°C
• Refractive Index: 1.574
• CAS DataBase Reference: 5,7-DIMETHOXYFLAVANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7-DIMETHOXYFLAVANONE(1036-72-2)
• EPA Substance Registry System: 5,7-DIMETHOXYFLAVANONE(1036-72-2)

Safety Data

• Safety Statements: S22:Do not inhale dust.; S24/25:Avoid contact with skin and eyes.
• Hazardous Substances Data: 1036-72-2(Hazardous Substances Data)

Usage

General Description

5,7-DIMETHOXYFLAVANONE is a chemical compound belonging to the flavanone class, which is a type of flavonoid. It is derived from natural sources such as citrus fruits and exhibits a variety of biological activities. 5,7-DIMETHOXYFLAVANONE has been shown to possess antioxidant, anti-inflammatory, and anticancer properties. Additionally, 5,7-DIMETHOXYFLAVANONE has been studied for its potential neuroprotective effects and its ability to modulate the immune response. Due to its diverse pharmacological activities, 5,7-DIMETHOXYFLAVANONE has attracted attention for its potential therapeutic applications in the treatment of various diseases and conditions. Further research on this compound may reveal its full potential and contribute to the development of novel drugs and treatments.

InChI:InChI=1/C17H16O4/c1-19-12-8-15(20-2)17-13(18)10-14(21-16(17)9-12)11-6-4-3-5-7-11/h3-9,14H,10H2,1-2H3

Upstream product

• 100-52-7 benzaldehyde 
• 54107-66-3 5,7-dimethoxy-4-chromanone 
• 98-80-6 phenylboronic acid 
• 501428-25-7 3-(3',5'-dimethoxyphenoxy)propionitrile 
• 1775-97-9 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylpropenone 
• 21392-57-4 Dimethyl-chrysin 
• 500-99-2 3,5-dimethoxyphenol 
• 18956-15-5 pinostrobin chalcone 
• 19309-14-9 cardamomin 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 1775-97-9 flavokawain B 
• 123-54-6 acetylacetone 
• 89329-19-1 3,5-dimethoxyphenylcinnamate 
• 141-97-9 ethyl acetoacetate 

Downstream Products

• 99111-06-5 5,7-dimethoxy-3-N,N-dimethylaminomethylidene-flavanone 
• 1193346-73-4 5,7-dimethoxyflavanone oxime 
• 124259-95-6 2-(1,5-diphenyl-1H-pyrazol-3-yl)-3,5-dimethoxyphenol 
• 98770-02-6 4-chloro-3,8-diformyl-5,7-dimethoxy-flav-3-ene 
• 15236-07-4 3-Hydroxy-5,7-dimethoxyflavone 
• 2569-86-0 5,8-dihydroxy-7-methoxyflavanone 
• 851606-11-6 5,7-dimethoxy-2-phenylchroman-4-one (4-nitrophenyl)hydrazone 
• 26964-35-2 5,7-dimethoxyisoflavone 
• 18956-15-5 pinostrobin chalcone 
• 480-39-7 pinocembrin 
• 1775-97-9 flavokawain B 
• 480-37-5 pinostrobin 
• 42508-82-7 2,4-trans-5,7-dimethoxyflavan-4-ol 
• 42508-82-7 5,7-dimethoxyflavan-4β-ol 

Relevant articles and documents

Antimutagenic activity of flavonoids from Sozuku

Pinocembrin (1) and cardamonin (2) from Sozuku showed a suppressive effect on umu gene expression of SOS response in Salmonella typhimurium TA1535/pSK1002 against the mutagen furylfuramide. Compounds 1 and 2 suppressed 52% and 36% of SOS-inducing activity at a concentration of 0.20?μmol/mL. The ID50 value of 1 was 0.18?μmol/mL. These compounds showed the suppression of 2-amino-3,4-dimethylimidazo-[4,5-f]quinolone (MeIQ) and UV irradiation-induced SOS response. Pinostrobin (3) and 5,7-dimethoxyflavanone (4), methyl ethers of 1, showed similar activity to 1 against MeIQ-induced SOS response, but that of furylfuramide and UV irradiation were decreased. On the other hand, compounds 1–4 did not show the suppression of activated MeIQ-induced SOS response. Furthermore, compounds 1–4 showed potent antimutagenic activity against MeIQ mutagenesis in Ames test using the S. typhimurium TA100 and TA98 strains.

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Attrition-enhanced deracemization and absolute asymmetric synthesis of flavanones from prochiral precursors

Seven racemic 5,7-dimethoxyflavanones afforded conglomerate crystals upon recrystallization from a solvent. Three methodologies were investigated to achieve asymmetric transformation based on dynamic crystallization of the chiral conglomerate system. The first was chiral symmetry breaking of racemic flavanones by attrition-enhanced deracemization. Continuous suspension of racemic flavanones in a small amount of propanol in the presence of a base (1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)) and glass beads promoted chiral symmetry breaking and converted the flavanones to crystals of (+)- or (-)-enantiomers with 78 to 99% ee. The second method involved cyclization of the intermediate aldol product to give optically active flavanone with 90% ee involving a reversible oxa-Michael addition reaction with attrition-enhanced deracemization. The third was a reaction starting from prochiral 2-hydroxy-4,6-dimethoxyacetophenone and 2-naphthaldehyde under basic conditions, which gave the corresponding flavanone in 89% ee.

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.