38302-15-7

Basic information

• Product Name: Naringenin trimethyl ether
• Synonyms: Naringenin trimethyl ether;5,7,4'-trimethoxyflavanone
• CAS NO: 38302-15-7
• Molecular Formula: C18H18O5
• Molecular Weight: 314
• EINECS: 200-258-5
• Mol File: 38302-15-7.mol
• Article Data: 24

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Naringenin trimethyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: Naringenin trimethyl ether(38302-15-7)
• EPA Substance Registry System: Naringenin trimethyl ether(38302-15-7)

Safety Data

• Hazardous Substances Data: 38302-15-7(Hazardous Substances Data)

Usage

General Description

Naringenin trimethyl ether is a natural chemical compound found in certain plants, and is a derivative of the flavonoid naringenin. It is also known as 5,7,4'-Trimethoxyflavanone or Hesperetin trimethyl ether. Naringenin trimethyl ether has been studied for its potential health benefits, including its anti-inflammatory and antioxidant properties. It has also been investigated for its potential in treating conditions such as cancer, diabetes, and cardiovascular diseases. Additionally, naringenin trimethyl ether has shown potential as a skincare ingredient due to its ability to protect skin cells from UV-induced damage and to improve skin elasticity. Overall, naringenin trimethyl ether is a bioactive compound with promising potential for various health and skincare applications.

Upstream product

• 75-11-6 diiodomethane 
• 3420-72-2 2'-hydroxy-4,4',6'-trimethoxychalcone 
• 480-41-1 naringenin 
• 74-88-4 methyl iodide 
• 66074-95-1 4',5,7-trimethoxyflavanone 
• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 
• 54107-66-3 5,7-dimethoxy-4-chromanone 
• 5720-07-0 4-methoxyphenylboronic acid 
• 501428-25-7 3-(3',5'-dimethoxyphenoxy)propionitrile 
• 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 

Downstream Products

• 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 
• 98752-29-5 8-chloro-5,7,4'-trimethoxyflavanone 

Relevant articles and documents

A CHALCONE GLYCOSIDE FROM ACACIA DEALBATA

A new yellow pigment isolated from the flowers of Acacia dealbata has been shown to be chalcononaringenin 2'-4)-xyloside> by chemical and spectroscopic methods. - Key Word Index - Acacia dealbata; Leguminosae; flowers; 4,2',4',6'-tetrahydroxychalcone 2'-4)-xyloside>.

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.