1251-84-9

Usage

Uses

Used in Pharmaceutical Industry:
Quercetagetin 3,5,6,7,3',4'-hexamethyl ether is used as a potential therapeutic agent for its antioxidant, anti-inflammatory, and antimicrobial properties. These properties may contribute to the development of new treatments for various diseases and conditions, although further research is needed to determine its exact mechanism of action and therapeutic benefits.
Used in Cosmetic Industry:
In the cosmetic industry, Quercetagetin 3,5,6,7,3',4'-hexamethyl ether may be used as an active ingredient in skincare products due to its antioxidant and anti-inflammatory properties. These properties could help protect the skin from environmental damage, reduce inflammation, and promote a healthier skin appearance.
Used in Food Industry:
Quercetagetin 3,5,6,7,3',4'-hexamethyl ether could be used as a natural preservative in the food industry, thanks to its antimicrobial properties. This could help extend the shelf life of food products and maintain their quality, while also providing potential health benefits due to its antioxidant properties.
Used in Agricultural Industry:
In agriculture, Quercetagetin 3,5,6,7,3',4'-hexamethyl ether may be used as a natural pesticide or fungicide, leveraging its antimicrobial properties to protect crops from diseases and pests. This could offer a more sustainable and environmentally friendly alternative to synthetic chemical pesticides.
Note: The uses mentioned above are speculative based on the provided information and the known properties of Quercetagetin 3,5,6,7,3',4'-hexamethyl ether. Further research and development are required to validate these applications and ensure their safety and efficacy.

InChI:InChI=1/C21H22O8/c1-23-12-8-7-11(9-13(12)24-2)18-21(28-6)17(22)16-14(29-18)10-15(25-3)19(26-4)20(16)27-5/h7-10H,1-6H3

Upstream product

• 72947-60-5 2-(3,4-dimethoxy-phenyl)-6-hydroxy-3,5,7-trimethoxy-chromen-4-one 
• 77-78-1 dimethyl sulfate 
• 63296-15-1 5,6-dihydroxy-3,7,3′,4′-tetramethoxyflavone 
• 186581-53-3 diazomethane 
• 5188-73-8 axillarin 
• 3153-83-1 spinacetin 
• 74-88-4 methyl iodide 
• 479-91-4 casticin 
• 80-11-5 N-methyl-N-nitrosotoluene-p-sulfonamide 
• 65602-55-3 2-(3,4-dimethoxy-phenyl)-3-hydroxy-5,6,7-trimethoxy-chromen-4-one 
• 65602-54-2 2'-hydroxy-3,4,4',5',6'-pentamethoxychalcone 
• 22248-14-2 6-hydroxy-2,3,4-trimethoxyacetophenone 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 642-71-7 3,4,5-trimethoxyphenol 

Downstream Products

• 479-90-3 artemetin 
• 2798-20-1 gardenin B 
• 19103-54-9 5-hydroxy-4',6,7-trimethoxyflavone 
• 21763-80-4 5-desmethylsinensetin 
• 2174-59-6 5-hydroxy-6,7,8,3',4'-pentamethoxyflavone 
• 1176-88-1 5-hydroxy-3,6,7,8,3',4'-hexamethoxyflavone 
• 124909-90-6 Toluene-4-sulfonic acid 2-(3,4-dimethoxy-phenyl)-3,6,7-trimethoxy-4-oxo-4H-chromen-5-yl ester 
• 124909-97-3 Toluene-4-sulfonic acid 2-(3,4-dimethoxy-phenyl)-3-hydroxy-6,7-dimethoxy-4-oxo-4H-chromen-5-yl ester 
• 104055-81-4 Acetic acid 3-acetoxy-2-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-4-oxo-4H-chromen-5-yl ester 
• 57296-14-7 3,5-dihydroxy-6,7,3′,4′-tetramethoxyflavone 

Relevant academic research and scientific papers

QUERCETAGETIN 6,7,4'-TRIMETHYL ETHER AND 3-SULPHATE FROM DECACHAETA HAENKEANA

Four 6-methoxylated flavonols, including a new quercetagetin derivative and its 3-potassium sulphate salt, were isolated from the aerial parts of Decachaeta haenkeana.Key Word Index - Decachaeta haenkeana; Compositae; Eupatorieae; 6-methoxyflavonols; flavonol sulphate.

QUERCETAGETIN 5-METHYL ETHER FROM THE PETALS OF TAGETES PATULA

Key Word Index - Tagetes patula; Compositae; flavones; luteolin; allopatuletin; 3,6,7,3',4'-pentahydroxy-5-methoxyflavone.

Synthesis and anti-proliferative activities of 5,6,7-trimethoxyflavones and their derivatives

A series of 5,6,7-trimethoxyflavones 1a-1g and their derivatives 2a-2g, 3a-3d, 4 and 5, including the natural products 5,6,7-trimethoxy-4’-hydroxyflavone (1a), 5,6,7,3’,4’ -pentamethoxyflavone (sinensetin, 1 b), 5,6,7-trimethoxy-3’,4’-methyl enedioxy flavone (1c), 5,6,7,3’-tetramethoxy-4,5’-methylenedioxyflavone (1e), 5,6,7, 3’,4’,5’-hextamethoxyflavone (1 g), 5-hydroxy-3,4,2’,3’,4’-pentamethoxy chal-cone (2 b), 5,4’-dihydroxy-6,7-dimethoxy flavone (cirsimaritin, 3a) and 5-hydroxy-6,7,3’, 4’-tetramethoxyflavone (5-demethylsinensetin, 3 b), 3,5,6,7,3’,4’-hexamethoxyflavone (3-methoxysinensetin, 4) and 5’-hydroxy-3,6,7,3’,4’-pentamethoxyflavone (5) were synthesized. Their anti-proliferative activity in?vitro was evaluated against a panel of four human cancer cell lines (Aspc-1, HCT-116, HepG-2 and SUN-5) by the CTG assay. The results showed that most of the synthetic compounds exhibited moderate to high anti-proliferative activities. In particular, compound 3c possess IC50 (5.30 μM) values below 10 μM against Aspc-1 cells and are worthy of further investigation.

Correlation study on methoxylation pattern of flavonoids and their heme-targeted antiplasmodial activity

A library of 33 polymethoxylated flavones (PMF) was evaluated for heme-binding affinity by biomimetic MS assay and in vitro antiplasmodial activity on two strains of P. falciparum. Stability of heme adducts was discussed using the dissociation voltage at 50% (DV50). No correlation was observed between the methoxylation pattern and the antiparasitic activity, either for the 3D7 chloroquine-sensitive or for the W2 chloroquine-resistant P. falciparum strains. However, in each PMF family an increased DV50 was observed for the derivatives methoxylated in position 5. Measurement of intra-erythrocytic hemozoin formation of selected derivatives was performed and hemozoin concentration was inversely correlated with heme-binding affinity. Kaempferol showed no influence on hemozoin formation, reinforcing the hypothesis that this compound may exert in vitro antiplasmodial activity mostly through other pathways. Pentamethoxyquercetin has simultaneously demonstrated a significant biological activity and a strong interaction with heme, suggesting that inhibition of hemozoin formation is totally or partially responsible for its antiparasitic effect.

Cytotoxic flavone analogues of vitexicarpin, a constituent of the leaves of Vitex negundo

Bioassay-guided fractionation of the chloroform-soluble extract of the leaves of Vitex negundo led to the isolation of the known flavone vitexicarpin (1), which exhibited broad cytotoxicity in a human cancer cell line panel. In an attempt to increase the

STUDIES OF THE SELECTIVE O-ALKYLATION AND DEALKYLATION OF FLAVONOIDS. XII. A NEW, CONVENIENT METHOD FOR SYNTHESIZING 3,5-DIHYDROXY-6,7-DIMETHOXYFLAVONES FROM 3,5,6,7-TETRAMETHOXYFLAVONES

The 5-methoxy group on 3,5,6,7-tetramethoxyflavones and the 3-methoxy group on 3,6,7-trimethoxy-5-tosyloxy-flavones were selectively cleaved with anhydrous aluminum bromide in acetonitrile under controlled conditions without the cleavage of benzyloxy groups on the B ring.By the application of these reactions, seven 3,5-dihydroxy-6,7-dimethoxyflavones were easily synthesized from the corresponding 3,5,6,7-tetramethoxyflavones which were synthesized from 3,6-dihydroxy-2,4ω-trimethoxycetophenone by means of the Allan-Robinson reaction followed by methylation.Keywords: Allan-Robinson reaction ; selective demethylation; 3,5,6,7-tetramethoxyflavone; 5-hydroxy-3,6,7-trimethoxyflavone; 6-hydroxy-3,5,7-trimethoxyflavone; 5-tosyloxyflavone; 5,6-dihydroxy-3,7-dimethoxyflavone; 3,5-dihydroxy-6,7-dimethoxyflavone, 3,5-diacetoxy-6,7-dimethoxyflavone

ANTIMICROBIAL FLAVONOIDS FROM PSIADIA TRINERVIA AND THEIR METHYLATED AND ACETYLATED DERIVATIVES

Key Word Index - Psiadia trinervia; Compositae; flavonoids; antifungal; antibacterial; Cladosporium cucumerinum; Bacillus cereus; bioautography.Abstract - From a dichloromethane extract and a hydrolysed methanolic extract from the leaves of Psiadia trinervia, 13 3-methylated flavonol have beeen isolated.Their structures were established by the usual spectoscopic methods (UV, EIMS, 1H and 13CNMR).Ayanin, casticin, chrysosplenol-D and 5,7,4'-trihydroxy-3,8-dimethoxyflavone were responsible for the antifungal activity found in the preliminary screening.Chrysosplenol-D, isokaemferide, 5,7,4'-trihydroxy-3,3'-dimethoxyflavone and 5,7,4'-trihydroxy-3,8-dimethoxyflavone displayed antibacterial activity.Twenty-nine derivatives were prepared by permethylation and selective methylation of the free hydroxyl group at C-5.The antimicrobial activities of the isolates and derivatives were determined by bioautographic assays using C. cucumerinum and B. cereus as test organisms.

FLAVONOL GLYCOSIDES IN LEAVES OF SPINACIA OLERACEA

Besides spinatoside (3,6-dimethoxy-5,7,3',4'-tetrahydroxyflavone 4'-O-β-D-glucopyranuronide), three new flavonol glycosides have now been isolated from the polar fractions of the methanolic extract of Spinacia oleracea.They have been identified as patuletin 3-O-β-D-glucopyranosyl-(1->6)-2)>-β-D-glucopyranoside, patuletin 3-O-β-gentiobioside and spinacetin 3-O-β-gentiobioside, respectively. Key Word Index - Spinacia oleracea; Chenopodiaceae; spinach; 6-methoxy-3,5,7,3',4'-pentahydroxyflavone 3-O-β-D-glucosyl-(1->6)-2)>-β-D-glucoside; 6-methoxy-3,5,7,3',4'-pentahydroxyflavone 3-O-β-gentiobioside; 6,3'-dimethoxy-3,5,7,4'-tetrahydroxyflavone 3-O-β-D-gentiobiside; spinatoside.

STRUCTURAL ELUCIDATION OF POLYMETHOXYFLAVONES FROM SHIFT REAGENT PROTON NMR MEASUREMENTS

Key Word Index - Polymethoxyflavones; 1H NMR; shift reagents; Pr(fod)3; structural elucidation. The quantitative shift reagent behavior of polymethoxylated flavones in the presence of Pr(fod)3 shows that for structural elucidation of these molecules the degree of substitution on the neighbourhood of the carbonyl group can be determined from the number of signals that are strongly shifted and broadened.The induced shifts of the remaining signals are of complementary help and even the resonances of individual methoxy groups can be ascribed.