66074-95-1

Basic information

• Product Name: 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dimethoxy-2-(4-methoxyphenyl)-
• Synonyms: 5,7,4’-O,O,O-trimethoxynaringenin;4',5,7-trimethoxyflavanone;naringenin trimethyl ether;2,3-dihydro-5,7-dimethoxy-2-(4'-methoxyphenyl)-4H-1-benzopyran-4-one;5,7-dimethoxy-2-(4-methoxyphenyl)chroman-4-one;5,7,4'-Trimethoxyflavanone
• CAS NO: 66074-95-1
• Molecular Formula: C18H18O5
• Molecular Weight: 314.338
• Mol File: 66074-95-1.mol
• Article Data: 23

Chemical Properties

• CAS DataBase Reference: 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dimethoxy-2-(4-methoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dimethoxy-2-(4-methoxyphenyl)-(66074-95-1)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dimethoxy-2-(4-methoxyphenyl)-(66074-95-1)

Safety Data

• Hazardous Substances Data: 66074-95-1(Hazardous Substances Data)

Upstream product

• 75-11-6 diiodomethane 
• 3420-72-2 2'-hydroxy-4,4',6'-trimethoxychalcone 
• 343612-22-6 (E)-1-(2-hydroxy-4,5-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 
• 501428-25-7 3-(3',5'-dimethoxyphenoxy)propionitrile 
• 54107-66-3 5,7-dimethoxy-4-chromanone 
• 5720-07-0 4-methoxyphenylboronic acid 
• 123-11-5 4-methoxy-benzaldehyde 
• 830-09-1 3-(4'-methoxyphenyl)propenoic acid 
• 500-99-2 3,5-dimethoxyphenol 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 832-58-6 1-(2,4,6-trimethoxyphenyl)ethanone 
• 621-23-8 1,2,3-trimethoxybenzene 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 108-73-6 3,5-dihydroxyphenol 

Downstream Products

• 6626-61-5 6-Hydroxy-5,7,4'-trimethoxy-flavanon-⁽⁴⁾ 
• 119529-70-3 8-bromo-4',5,7-trimethoxyflavanone 
• 98752-29-5 8-chloro-5,7,4'-trimethoxyflavanone 
• 1162-82-9 4',5,7-trimethoxyisoflavone 
• 1227479-74-4 5,7,4'-trimethoxyflavanone oxime 
• 10493-01-3 4-hydroxy-5,7,4'-trimethoxyflavan 
• 38302-15-7 (2S)-4’,5,7-trimethoxyflavanone 
• 725740-09-0 5,7,4’-O,O,O-trimethoxy-8-methylnaringenin 
• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 
• 29424-96-2 naringenin-4',7-dimethyl ether 
• 81148-82-5 5-acetoxy-7,4′-dimethoxyflavanone 

Relevant articles and documents

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.

Total synthesis of agalloside, isolated from: Aquilaria agallocha, by the 5-O-glycosylation of flavan

Agalloside (1) is a neural stem cell differentiation activator isolated from Aquilaria agallocha by our group using Hes1 immobilized beads. We conducted the first total synthesis of agalloside (1) via the 5-O-glycosylation of flavan 25 using glycosyl fluoride 20 in the presence of BF3·Et2O. Subsequent oxidation with DDQ to flavanone 2 and deprotection successively provided agalloside (1). This synthetic strategy holds promise for use in the synthesis of 5-O-glycosylated flavonoids. The synthesized agalloside (1) accelerated neural stem cell differentiation, which is a result comparable to that for the naturally occurring compound 1.

A novel synthesis of naringenin and related flavanones

Efficient methods are reported for the preparation of naringenin (4',5,7-trihydroxyflavanone) which could be easily scaled-up. They have been applied to three other flavanones (6.hydroxyflavanone, 6,4'-dihydroxyflavanone, 6,3',4'-trihydroxyflavanone) suitably.