TAMARIXETIN

Base Information

• Chemical Name: TAMARIXETIN
• CAS No.: 603-61-2
• Molecular Formula: C16H12 O7
• Molecular Weight: 316.267
• Mol file: 603-61-2.mol

Synonyms:Flavone,3,3',5,7-tetrahydroxy-4'-methoxy- (7CI,8CI); Tamaraxetin (6CI);3,3',5,7-Tetrahydroxy-4'-methoxyflavone; 4'-Methoxyquercetin;4'-Methylquercetin; 4'-O-Methylquercetin; Quercetin 4'-methyl ether;Tamarixetin

Chemical Property of TAMARIXETIN

Chemical Property:

• Vapor Pressure: 4.47E-15mmHg at 25°C
• Melting Point: 265-268°C
• Boiling Point: 601.8oC at 760 mmHg
• PKA: 6.31±0.40(Predicted)
• Flash Point: 228.7oC
• PSA: 120.36000
• Density: 1.634g/cm3
• LogP: 2.29100

Purity/Quality:

≥98% ^*data from raw suppliers

4''-O-MethylQuercetin ^*data from reagent suppliers

Safty Information:

• Statements: 22
• Safety Statements: 22-45

MSDS Files:

SDS file from LookChem

Useful:

• Description: 4''-O-methyl Quercetin is a flavonoid isolated from C. ordata with anticancer and antiplasmodial activity. 4''-O-methyl Quercetin is a major metabolite of quercetin (Item No. 10005169) that inhibits the viability of HL-60, U937, MOLT-3, Raji, K562, MCF-7, SK-MEL-1, and A549 human tumor cell lines with IC50 values ranging from 5.5-24.1 μM. It induces G2-M arrest and inhibits tubulin polymerization in vitro in a dose-dependent manner. 4''-O-methyl Quercetin inhibits breast cancer resistance protein (BCRP/ABCG2; IC50 = 40 nM in a vesicular transport assay) with no cellular toxicity indicating potential for use in overcoming multidrug resistance in chemotherapy. 4''-O-methyl Quercetin also reduces in vitro proliferation of chloroquine-resistant P. falciparum (IC50 = 4.8 μM) and suppresses infection in mice (65-81% suppression at 2.5-5 mg/kg dose).
• Uses: A major metabolite of the flavanoid Quercetin (Q509500) with antioxidant properties. It helps to protect H9c2 cardiomyoblasts against H2O2-induced oxidative stress via the modulation of PI3K/Akt and ERK1/2 signaling pathways.

Technology Process of TAMARIXETIN

There total 37 articles about TAMARIXETIN which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,7-bis(methoxymethoxy)-4H-chromen-4-one (1197215-51-2) → tamarixetin (603-61-2)

Guidance literature:

With hydrogenchloride; In diethyl ether; dichloromethane; water; at 0 - 25 ℃;

DOI:10.3762/bjoc.5.60

Reference yield: 89.0%

3,7-bis(benzyloxy)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one (498548-16-6) → tamarixetin (603-61-2)

Guidance literature:

With 20% palladium hydroxide-activated charcoal; In ethanol; cyclohexene; for 1h; Inert atmosphere; Reflux;

DOI:10.1021/acs.jafc.0c04500

Reference yield: 81.0%

3',7-di-O-benzyl-4'-O-methylquercetin (1268621-74-4) → tamarixetin (603-61-2)

Guidance literature:

With 10% palladium on activated carbon; hydrogen; In ethanol; at 20 ℃; for 5.5h;

DOI:10.1055/s-0030-1258310

upstream raw materials:

2-benzoyloxy-1-(2,4,6-trihydroxy-phenyl)-ethanone

3,5,7,3'-tetrahydroxy-4'-methoxyflavanone

3,4'-O-dimethylquercetin

quercetol

Downstream raw materials:

3,5,7-triethoxy-2-(3-ethoxy-4-methoxy-phenyl)-chromen-4-one

quercetol

C₁₆H₁₀O₁₃S₂^(2-)*2K⁽¹⁺⁾

C₁₆H₉O₁₆S₃^(3-)*3K⁽¹⁺⁾