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

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

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 
• 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 
• 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 
• 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 

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 Polymethoxyflavonoids from Hesperidin and Naringin and their Antiproliferative Activity

[Figure not available: see fulltext.] A series of polymethoxyflavonoids were synthesized via cleavage of the glycosidic bond, dehydrogenation, selective methylation, bromination, nucleophilic aromatic substitution, O-prenylation, Claisen–Schmidt aldol condensation, cyclization, and oxidation from very abundant and inexpensive natural flavonoids hesperidin and naringin. The in vitro antiproliferative activity of the synthesized compounds was evaluated against a panel of four human cancer cell lines (Aspc-1, HCT-116, HepG-2, and SUN-5) by the CellTiter-Glo assay. The results showed that some of synthesized compounds exhibited moderate to high antiproliferative activity. Among them, (2E)-1-(2-hydroxy-3,4,5,6-tetramethoxyphenyl)-3-(7-methoxy-1,3-benzodioxol-5-yl)prop-2-en-1-one was revealed to be the most active with IC50 values ranging from 10.35 to 13.89 μM against all four cancer cell lines, the IC50 value (10.35 μM) being below positive control cisplatin (12.36 μM) against HepG-2 cells.

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.].

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

PROCESS TO PREPARE FLAVONES

The present invention relates to the field of flavor ingredients. More particularly it provides, a process for making 5- hydroxy -polyitιethoxy-f lavones (5-OH-PMF) (I) or improving the organoleptic properties of natural polymethoxy-f lavones (PMF) . The invention's process comprises treating flavones (II) in the presence of a HCl solution in a non-acidic and non -aqueous solvent. (I) (II).

Regioselective hydroxylation of 2-hydroxychalcones by dimethyldioxirane towards polymethoxylated flavonoids

The flavone nucleus is part of a large number of natural products and medicinal compounds. In this presentation the novel regioselective hydroxylation of hydroxyarenes with DMD is described. The results showed further that flavonoids with 5-hydroxy group were selectively oxyfunctionalized at the para-position C8 carbon atom by DMD. Finally, according to this methodology, the naturally occurring isosinensetin, tangeretin, sinensetin, nobiletin, natsudaidain, gardenin B, 3,3′,4′,5,6,7,8- heptamethoxyflavone, quercetin and its derivatives were synthesized.

Taste modifier and a method of modifying taste

Taste modifier comprising a flavone derivative as an active ingredient of the general formula (I): STR1 wherein R1, R3, R4, R6 and R8 are independently a methoxy group or an hydrogen atom, R2 and R7 are methoxy groups, and R5 is a methoxy group or an hydroxy group, and a method of modifying taste, comprising adding a taste-modifying effective amount of the flavone derivative (I) to a product used in a mouth or an orally ingestible product. Various factors associated with taste can be modified, for example, the derivative can enhance sourness, reduce saltiness, inhibit unpleasant lasting of sweetness, enhance refreshing flavor and its continuity, reduce flavor associated with acetic acid, and enhance body, deliciousness and savor associated with the combination of these tastes.