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

Description

GARDENIN B, also known as tangeretin, is a tetramethoxyflavone with a hydroxy group replacing the methoxy group at position 5. It is a naturally occurring compound found in citrus fruits, particularly in the peels of tangerines and oranges. GARDENIN B has been studied for its potential health benefits and applications in various industries.

Uses

Used in Pharmaceutical Industry:
GARDENIN B is used as a therapeutic agent for its potential anti-inflammatory, antioxidant, and anti-cancer properties. It has been shown to modulate various signaling pathways involved in cancer cell growth and proliferation, making it a promising candidate for the development of novel cancer treatments.
Used in Cosmetic Industry:
GARDENIN B is used as an active ingredient in skincare products for its antioxidant and anti-inflammatory properties. It can help protect the skin from environmental stressors, reduce inflammation, and promote overall skin health.
Used in Food and Beverage Industry:
GARDENIN B can be used as a natural additive in the food and beverage industry due to its antioxidant properties. It can help extend the shelf life of products by preventing oxidation and rancidity, as well as enhance the flavor and aroma of certain foods and beverages.
Used in Agricultural Industry:
GARDENIN B can be utilized in the agricultural industry as a natural pesticide or growth promoter. Its anti-inflammatory and antioxidant properties may help protect plants from various stressors, such as pests and diseases, and promote healthy growth.

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

• 2798-22-3 5,8-dihydroxy-6,7-dimethoxy-2-(4-methoxyphenyl)-4-benzopyrone 
• 77-78-1 dimethyl sulfate 
• 3420-72-2 2'-hydroxy-4,4',6'-trimethoxychalcone 
• 41929-26-4 1-(6-hydroxy-2,3,4-trimethoxyphenyl)-3-(4-methoxyphenyl)propenone 
• 19103-54-9 5-hydroxy-4',6,7-trimethoxyflavone 
• 1168-42-9 5,6,7,4'-tetramethoxyflavone 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 40110-96-1 4'-benzyloxy-5,6,7,8-tetramethoxyflavone 
• 36950-98-8 4'-hydroxy-5,6,7,8-tetramethoxy flavone 
• 40110-95-0 4-benzyloxy-2'-hydroxy-3',4',5',6'-tetramethoxychalcone 
• 3162-28-5 2-hydroxy-3,4,5,6-tetramethoxyacetophenone 
• 73898-14-3 4'-benzyloxy-5,6,7,8-tetramethoxyflavanone 
• 2306-27-6 sinensetin 
• 481-53-8 tangeritin 

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.

Synthesis of Citrus polymethoxyflavonoids and their antiproliferative activities on Hela cells

Abstract: A series of polymethoxyflavonoids (3–16) were synthesized through dehydrogenation, O-methylation, glycoside hydrolysis, bromination, microwave-assisted aromatic nucleophilic substitution, dimethyldioxirane oxidation and regioselective demethylation, starting from abundant and inexpensive natural sources naringin and hesperidin. All the synthetic compounds were test for antiproliferative activities on human cervical carcinoma Hela cell line by the standard CCK-8 assay, the result showed that most of the target compounds exhibited moderate to potent antiproliferative activities on Hela cells comparable with the positive control cis-Platin. Among them, 5-hydroxypolymethoxy flavonoid 13 showed the strongest activity (IC50 0.791 μM). Graphical Abstract: [InlineMediaObject not available: see fulltext.].

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