4382-17-6

Basic information

• Product Name: 3,3'-di-O-methylquercetin
• Synonyms: 3,3'-di-O-methylquercetin;2-(3-Methoxy-4-hydroxyphenyl)-3-methoxy-5,7-dihydroxy-4H-1-benzopyran-4-one;2-(4-Hydroxy-3-methoxyphenyl)-3-methoxy-5,7-dihydroxy-4H-1-benzopyran-4-one;3,3'-Dimethoxy-4',5,7-trihydroxyflavone;4',5,7-Trihydroxy-3,3'-dimethoxyflavone
• CAS NO: 4382-17-6
• Molecular Formula: C₁₇H₁₄O₇
• Molecular Weight: 330.29
• Mol File: 4382-17-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 257-258 °C
• Boiling Point: 604.8°C at 760 mmHg
• Flash Point: 226.4°C
• Appearance: /
• Density: 1.55g/cm³
• Vapor Pressure: 3.19E-15mmHg at 25°C
• Refractive Index: 1.7
• PKA: 6.31±0.40(Predicted)
• CAS DataBase Reference: 3,3'-di-O-methylquercetin(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3'-di-O-methylquercetin(4382-17-6)
• EPA Substance Registry System: 3,3'-di-O-methylquercetin(4382-17-6)

Safety Data

• Hazardous Substances Data: 4382-17-6(Hazardous Substances Data)

Usage

Description

3,3'-di-O-methylquercetin is a flavonoid compound derived from quercetin, a plant-based pigment with antioxidant properties. As a derivative, it features two methyl groups added to the quercetin molecule, which may influence its chemical properties and biological activity. 3,3'-di-O-methylquercetin is of interest in pharmaceutical and medical research due to its potential anti-inflammatory, anti-cancer, and neuroprotective effects, although its precise mechanisms and health benefits are still under investigation.

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

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

Relevant articles and documents

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.

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.