572-32-7

Basic information

• Product Name: AYANIN
• Synonyms: QUERCETIN 3,7,4'-TRIMETHYL ETHER;AYANIN;2-(3-Hydroxy-4-methoxyphenyl)-3,7-dimethoxy-5-hydroxy-4H-1-benzopyran-4-one;3',5-Dihydroxy-3,4',7-trimethoxyflavone;3,7,4'-Tri-O-methylquercetin;5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,7-dimethoxy-4H-1-benzopyran-4-one;Quercetin 3,4',7-trimethyl ether;4H-1-Benzopyran-4-one,5-hydroxy-2-(3-hydroxy-4-Methoxyphenyl)-3,7-diMethoxy-
• CAS NO: 572-32-7
• Molecular Formula: C₁₈H₁₆O₇
• Molecular Weight: 344.32
• Mol File: 572-32-7.mol
• Article Data: 17

Chemical Properties

• Melting Point: 173℃
• Boiling Point: 600.8°C at 760 mmHg
• Flash Point: 221.5°C
• Appearance: /
• Density: 1.45g/cm³
• Vapor Pressure: 4.97E-15mmHg at 25°C
• Refractive Index: 1.653
• PKA: 6.15±0.40(Predicted)
• CAS DataBase Reference: AYANIN(CAS DataBase Reference)
• NIST Chemistry Reference: AYANIN(572-32-7)
• EPA Substance Registry System: AYANIN(572-32-7)

Safety Data

• Hazardous Substances Data: 572-32-7(Hazardous Substances Data)

Usage

General Description

Ayanin is a flavonoid compound found in a variety of plants, including those in the Asteraceae and Apiaceae families. It is known for its antioxidant and anti-inflammatory properties, and has been associated with potential health benefits such as protecting against oxidative stress and inflammation-related diseases. Ayanin has also shown potential as a therapeutic agent for conditions such as cancer, cardiovascular disease, and neurodegenerative disorders due to its ability to modulate signaling pathways and cellular functions. Its diverse biological activities make ayanin an important target for further research into its potential as a natural remedy for various health conditions.

InChI:InChI=1/C18H16O7/c1-22-10-7-12(20)15-14(8-10)25-17(18(24-3)16(15)21)9-4-5-13(23-2)11(19)6-9/h4-8,19-20H,1-3H3

Upstream product

• 117-39-5 quercetol 
• 77-78-1 dimethyl sulfate 
• 186581-53-3 diazomethane 
• 1221398-17-9 6,8-dibromo-3,7-O-dimethyltamarixetin 
• 74-88-4 methyl iodide 
• 1612925-22-0 5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-3-methoxy-4H-chromen-4-one 
• 116973-12-7 5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-3-hydroxy-4H-chromen-4-one 
• 153-18-4 rutin 
• 1486-70-0 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-3-methoxy-chromen-4-on 
• 33429-83-3 3,4'-O-dimethylquercetin 

Downstream Products

• 1245-15-4 retusin 
• 95938-85-5 2-(3-acetoxy-4-methoxy-phenyl)-3,5,7-trimethoxy-chromen-4-one 
• 1832-98-0 3'-hydroxy-3,5,7,4'-tetramethoxyflavone 
• 979-92-0 S-(5'-adenosyl)-L-homocysteine 
• 124458-89-5 3'-acetoxy-5-hydroxy-3,7,4'-trimethoxyflavone 
• 72947-72-9 5,3'-dihydroxy-3,7,4'-trimethoxyflavone diacetate 

Relevant articles and documents

Synthesis, characterization, and cross-linking strategy of a quercetin-based epoxidized monomer as a naturally-derived replacement for BPA in epoxy resins

The natural polyphenolic compound quercetin was functionalized and cross-linked to afford a robust epoxy network. Quercetin was selectively methylated and functionalized with glycidyl ether moieties using a microwave-assisted reaction on a gram scale to a

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.

A simple and effective preparation of quercetin pentamethyl ether from quercetin

Among the five hydroxy (OH) groups of quercetin (3,5,7,3',4'-pentahydroxyflavone), the OH group at 5 position is the most resistant to methylation due to its strong intramolecular hydrogen bonding with the carbonyl group at 4 position. Thus, it is generally difficult to synthesize the pentamethyl ether efficiently by conventional methylation. Here, we describe a simple and effective perO-methylation of quercetin with dimethyl sulfate in potassium (or sodium) hydroxide/dimethyl sulfoxide at room temperature for about 2 hours, affording quercetin pentamethyl ether (QPE) quantitatively as a single product. When methyl iodide was used in place of dimethyl sulfate, the C-methylation product 6-methylquercetin pentamethyl ether was also formed. A computational study provided a rationale for the experimental results.