4382-17-6

Usage

Uses

Used in Pharmaceutical and Medical Research:
3,3'-di-O-methylquercetin is used as a subject of study for its potential anti-inflammatory properties, which may help in managing inflammation-related conditions.
3,3'-di-O-methylquercetin is used as a subject of study for its potential anti-cancer properties, suggesting it may contribute to the development of cancer treatment strategies by targeting cancer cells or enhancing the effectiveness of existing therapies.
3,3'-di-O-methylquercetin is used as a subject of study for its potential neuroprotective effects, indicating it may play a role in protecting the nervous system and potentially be utilized in treatments for neurodegenerative diseases.
Used in Antioxidant Applications:
3,3'-di-O-methylquercetin is used as an antioxidant compound for its ability to neutralize free radicals, potentially reducing oxidative stress and contributing to overall health and wellness.
Used in Nutraceutical Development:
3,3'-di-O-methylquercetin is used as a component in the development of nutraceuticals, leveraging its potential health benefits for incorporation into dietary supplements and functional foods.

InChI:InChI=1/C17H14O7/c1-22-12-5-8(3-4-10(12)19)16-17(23-2)15(21)14-11(20)6-9(18)7-13(14)24-16/h3-7,18-20H,1-2H3

Upstream product

• 1486-70-0 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-3-methoxy-chromen-4-on 
• 485-80-3 S-adenosyl-L-methionine 
• 117-39-5 quercetol 
• 74-88-4 methyl iodide 

Downstream Products

• 26305-93-1 quercetin 3,3'-di-O-methyl ether triacetate 
• 117-39-5 quercetol 
• 90179-86-5 6-prenyl-5,7,4'-trihydroxy-3,3'-dimethoxyflavone 
• 90179-85-4 8-prenyl-5,7,4'-trihydroxy-3,3'-dimethoxyflavone 
• 53766-24-8 4',5-dihydroxy-3,3'-dimethoxy-7-(3-methylbut-2-enyloxy)flavone 
• 124458-93-1 7,4'-diacetyloxy-5-hydroxy-3,3'-dimethoxyflavone 
• 1247-97-8 pentamethyl quercetin 
• 13459-09-1 4′,7-dihydroxy-3,3′,5-trimethoxyflavone 
• 124458-94-2 7-acetoxy-2-(4-acetoxy-3-methoxy-phenyl)-3,5-dimethoxy-chromen-4-one 
• 90179-88-7 6-prenyl-5,4'-dihydroxy-3,7,3'-trimethoxyflavone 
• 40073-85-6 8-prenyl-5,4'-dihydroxy-3,7,3'-trimethoxyflavone 

Relevant academic research and scientific papers

Two methoxylated flavone glycosides from Bidens pilosa

Two methoxylated flavone glycosides were identified as the novel quercetin 3,3'-dimethyl ether 7-O-α-L-rhamnopyranosyl-(I → 6)-β-D- glucopyranoside and the known quercetin 3,3'-dimethyl ether 7-O-β-D- glucopyranoside from the roots of Bidens pilosa.

Characterization of a Flavonoid 3’/5’/7-O-Methyltransferase from Citrus reticulata and Evaluation of the in Vitro Cytotoxicity of Its Methylated Products

O-methylation of flavonoids is an important modification reaction that occurs in plants. O-methylation contributes to the structural diversity of flavonoids, which have several biological and pharmacological functions. In this study, an O-methyltransferase gene (CrOMT2) was isolated from the fruit peel of Citrus reticulata, which encoding a multifunctional O-methyltransferase and could effectively catalyze the methylation of 3’-, 5’-, and 7-OH of flavonoids with vicinal hydroxyl substitutions. Substrate preference assays indicated that this recombinant enzyme favored polymethoxylated flavones (PMF)-type substrates in vitro, thereby providing biochemical evidence for the potential role of the enzyme in plants. Additionally, the cytotoxicity of the methylated products from the enzymatic catalytic reaction was evaluated in vitro using human gastric cell lines SGC-7901 and BGC-823. The results showed that the in vitro cytotoxicity of the flavonoids with the unsaturated C2-C3 bond was increased after being methylated at position 3’. These combined results provide biochemical insight regarding CrOMT2 in vitro and indicate the in vitro cytotoxicity of the products methylated by its catalytic reaction.

Quercetin analogs with high fetal hemoglobin-inducing activity

β-Thalassemia is the major health problems in developing countries, when affected patients and healthy carriers are numerous, resulting a total absence or severe decrease in the production of β-globin chains. The use of chemical agents for increasing the production of fetal hemoglobin (HbF) by reactivating γ-globin gene to balance excess α-globin chains is an alternative therapeutic approach. Therefore, the search for molecules exhibiting the property of inducing γ-globin gene expression is of great interest. In this report, we discovered that quercetin (1), the major flavonoid isolated from the heartwoods of the medicinal plant Anaxagorea luzonensis promoted the expression of γ-globin gene. Chemical modification of 1 to fourteen methyl ether analogs (2?15) was conducted. The structures of these compounds were established on the basis of their spectroscopic data and by comparison with those of the reported values. The parent flavonoid and its chemically modified analogs were investigated for their γ-globin gene induction for the first time. The parent compound 1 exhibited less induced γ-globin gene expression than cisplatin and hemin, the positive controls. 3,4′-Di-O-methylquercetin (7), the modified analog, significantly enhanced γ-globin gene expression with 2.6-fold change at 8 μM, which was slightly higher than cisplatin and hemin. Moreover, compounds 1 and 7 displayed less cytotoxic activity against K562::ΔGγAγEGFP cells than cisplatin. Structure-activity relationship (SAR) study revealed that the methoxyl groups at the 3- and 4?-positions and the free hydroxyl group at the 7-position are required for strong HbF-inducing activity.

A FLAVONOL GLUCOSIDE FROM TYPHA LATIFOLIA

Chromatographic separation of the butanol-soluble part of the methanol extract of Typha latifolia leaves resulted in the isolation of a new flavonoid, 3,3'-di-O-methylquercetin 4'-O-glucosode, together with the known isorhamnetin 3-O-glucoside and 3-O-neohesperidoside. - Key Word Index: Typha latipholia; Typhaceae; flavonoid glucoside; 3,3'-di-O-methylquercetin 4'-O-glucoside.