2798-20-1

Basic information

• Product Name: GARDENIN B
• Synonyms: GARDENIN B;4',6,7,8-Tetramethoxy-5-hydroxyflavone;5-Hydroxy-4',6,7,8-tetramethoxyflavone;5-O-Desmethyltangeretin;5-DesMethyltangeretin;5-O-DeMethyltangeretin;Demethyltangeretin;Demethyltangeretin/Gardenin B
• CAS NO: 2798-20-1
• Molecular Formula: C₁₉H₁₈O₇
• Molecular Weight: 358.34
• Product Categories: Miscellaneous Natural Products
• Mol File: 2798-20-1.mol
• Article Data: 9

Chemical Properties

• Melting Point: 180-181℃
• Boiling Point: 582°C at 760 mmHg
• Flash Point: 210.8°C
• Appearance: /
• Density: 1.309±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 3.8E-14mmHg at 25°C
• Refractive Index: 1.593
• PKA: 6.83±0.40(Predicted)
• CAS DataBase Reference: GARDENIN B(CAS DataBase Reference)
• NIST Chemistry Reference: GARDENIN B(2798-20-1)
• EPA Substance Registry System: GARDENIN B(2798-20-1)

Safety Data

• Hazardous Substances Data: 2798-20-1(Hazardous Substances Data)

Usage

Definition

ChEBI: A tetramethoxyflavone that is tangeretin in which the methoxy group at position 5 has been replaced by a hydroxy group.

InChI:InChI=1/C19H18O7/c1-22-11-7-5-10(6-8-11)13-9-12(20)14-15(21)17(23-2)19(25-4)18(24-3)16(14)26-13/h5-9,21H,1-4H3

Upstream product

• 4397-53-9 p-benzyloxybenzaldehyde 
• 40110-96-1 4'-benzyloxy-5,6,7,8-tetramethoxyflavone 
• 1168-42-9 5,6,7,4'-tetramethoxyflavone 
• 2306-27-6 sinensetin 
• 481-53-8 tangeritin 
• 1251-84-9 3,5,6,7,3',4'-Hexamethoxyflavon 
• 478-01-3 nobiletin 
• 1178-24-1 3,3',4',5,6,7,8-heptamethoxyflavone 
• 16545-23-6 xanthomicrol 
• 77-78-1 dimethyl sulfate 
• 17306-46-6 rhoifolin 
• 124-41-4 sodium methylate 
• 73213-66-8 7-hydroxy-5,6,8,4′-tetramethoxyflavone 
• 73898-14-3 4'-benzyloxy-5,6,7,8-tetramethoxyflavanone 

Downstream Products

• 481-53-8 tangeritin 

Relevant articles and documents

Methoxyflavones from Stachys glutinosa with binding affinity to opioid receptors: In silico, in vitro, and in vivo studies

Fractionation of the bioactive dichloromethane extract from the aerial parts of Stachys glutinosa led to the isolation of four flavones, xanthomicrol (1), sideritoflavone (2), 8-methoxycirsilineol (3), and eupatilin (4), along with two neo-clerodane diterpenes, roseostachenone (8) and a new compound, 3α,4α-epoxyroseostachenol (7). In order to study structure-activity relationships, two methoxyflavones [5-demethyltangeretin (5) and tangeretin (6)] were synthesized by the methoxylation of xanthomicrol. The isolated compounds (1-4, 7, and 8) as well as the xanthomicrol semisynthetic derivatives (5 and 6) were evaluated for their binding affinity to the μ and δ opioid receptors. Xanthomicrol was the most potent binder to both μ and δ receptors, with a Ki value of 0.83 and 3.6 μM, respectively. Xanthomicrol administered intraperitoneally in mice at a dose of 80 mg/kg significantly reduced morphine-induced antinociception in the tail flick test. Our results suggested that xanthomicrol is a μ opioid receptor antagonist. Docking experiments were carried out to acquire a deeper understanding about important structural aspects of binding of xanthomicrol. In summary, these data suggest that xanthomicrol is a valuable structure for further development into a potential μ opioid receptor antagonist.

Use of flavone and flavanone derivatives in preparation of sedative and hypnotic drugs

Disclosed is a use of flavones derivatives and flavanone derivatives in preparation of sedative and hypnotic drugs.

Method of preparing demethylation form of polymethoxylated flavone from citrus skin

The present invention provides a method of using citrus skin to prepare demethylation form of polymethoxylated flavone, comprising steps of acid treatment, heating, cooling, neutralization and extraction, and using microwave heating and high temperature/p