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

General Description

3,3'-di-O-methylquercetin is a chemical compound belonging to the class of flavonoids, which are plant-based pigments known for their antioxidant properties. It is a derivative of quercetin, a well-studied flavonoid found in many fruits and vegetables. The addition of two methyl groups to the quercetin molecule alters its chemical properties, potentially affecting its biological activity and interactions with other molecules. 3,3'-di-O-methylquercetin has been studied for its potential anti-inflammatory, anti-cancer, and neuroprotective effects, making it a subject of interest in pharmaceutical and medical research. Its precise mechanisms of action and potential health benefits are currently under investigation.

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.