603-61-2

Basic information

• Product Name: TAMARIXETIN
• Synonyms: 4'-METHOXY-3,3',5,7-TETRAHYDROXYFLAVONE;4'-METHOXY-3,5,7,3'-TETRAHYDROFLAVONE;3,3',5,7 TETRAHYDROXY-4'-METHOXYFLAVONE;TAMARIXETIN;QUERCETIN-4'-METHYL ETHER;3,3’,5,7-tetrahydroxy-4’-methoxy-flavon;3,5,7-trihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4h-1-benzopyran-4-on;4’-methoxy-3,3’,5,7-tetrahydroxy-flavon
• CAS NO: 603-61-2
• Molecular Formula: C₁₆H₁₂O₇
• Molecular Weight: 316.26
• EINECS: 210-050-7
• Product Categories: Flavanols;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 603-61-2.mol
• Article Data: 20

Chemical Properties

• Melting Point: 265-268°C
• Boiling Point: 601.8oC at 760 mmHg
• Flash Point: 228.7oC
• Appearance: /
• Density: 1.634g/cm3
• Vapor Pressure: 4.47E-15mmHg at 25°C
• Refractive Index: 1.74
• PKA: 6.31±0.40(Predicted)
• CAS DataBase Reference: TAMARIXETIN(CAS DataBase Reference)
• NIST Chemistry Reference: TAMARIXETIN(603-61-2)
• EPA Substance Registry System: TAMARIXETIN(603-61-2)

Safety Data

• Statements: 22
• Safety Statements: 22-45
• Hazardous Substances Data: 603-61-2(Hazardous Substances Data)

Usage

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.

Definition

ChEBI: A monomethoxyflavone that is quercetin methylated at position O-4'. Isolated from Cyperus teneriffae.

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

InChI:InChI=1/C16H12O7/c1-22-11-3-2-7(4-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3

Upstream product

• 1197215-51-2 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,7-bis(methoxymethoxy)-4H-chromen-4-one 
• 1268621-74-4 3',7-di-O-benzyl-4'-O-methylquercetin 
• 1197215-50-1 2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-bis(methoxymethoxy)-4H-chromen-4-one 
• 1197215-49-8 2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-5-hydroxy-3,7-bis(methoxymethoxy)-4H-chromen-4-one 
• 520-33-2 hesperetin 
• 621-59-0 isovanillin 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 77-78-1 dimethyl sulfate 
• 153-18-4 rutin 
• 117-39-5 quercetol 
• 5779-98-6 O-methoxymethylisovanillin 
• 36804-11-2 2,4,6-tri-MOM phloracetophenone 
• 1334307-45-7 C₂₄H₃₀O₁₁ 

Downstream Products

• 116097-15-5 C₁₆H₁₀O₁₃S₂^(2-)*2K⁽¹⁺⁾ 
• 116097-16-6 C₁₆H₉O₁₆S₃^(3-)*3K⁽¹⁺⁾ 
• 1221398-16-8 6,8-dibromotamarixetin 
• 7690-17-7 3,5,7-triacetoxy-2-(3-acetoxy-4-methoxy-phenyl)-chromen-4-one 
• 37077-71-7 2-(3-acetoxy-4-methoxyphenyl)-7-hydroxy-4-oxo-4H-chromene-3,5-diyl diacetate 
• 1204142-68-6 8-(3,3-dimethylallyl)tamarixetin 
• 1383545-68-3 2-(3-acetoxy-4-methoxyphenyl)-8-(3-methylbut-2-enyl)-4-oxo-4H-chromene-3,5,7-triyl triacetate 
• 1383545-63-8 2-(3-acetoxy-4-methoxyphenyl)-7-(2-methylbut-3-en-2-yloxy)-4-oxo-4H-chromene-3,5-diyl diacetate 
• 1219698-80-2 C₂₅H₁₈O₁₁ 
• 1219698-81-3 C₂₅H₁₈O₁₁ 
• 64184-96-9 2-ethoxy-1-(2,4-diethoxy-6-hydroxy-phenyl)-ethanone 
• 117-39-5 quercetol 
• 7678-38-8 3,5,7-triethoxy-2-(3-ethoxy-4-methoxy-phenyl)-chromen-4-one 

Relevant articles and documents

Flavonoid compound as well as synthesis method and application thereof

The invention relates to a semi-synthetic flavonoid compound and an anti-inflammatory application thereof. The invention belongs to the technical field of medicines, particularly relates to synthesis of derivatives of natural products and an application of the derivatives in the anti-inflammatory aspect, and more particularly relates to a synthesis method of flavonoid compounds and an application of the flavonoid compounds in the anti-inflammatory aspect. According to the method, hesperetin is taken as a raw material, flavonol aglycone is synthesized, and finally flavonoid glycoside is synthesized through debenzylation and acetyl reaction. According to the invention, 32 flavonoid compounds, including 14 flavonoid aglycones and 18 flavonoid glycosides, including 15 known compounds and 17 unreported compounds, are synthesized in total. The part of the compounds show good in-vitro anti-inflammatory activity and can become anti-inflammatory drugs or lead compounds.

Glucuronidation of Methylated Quercetin Derivatives: Chemical and Biochemical Approaches

Botanical supplements derived from grapes are functional in animal model systems for the amelioration of neurological conditions, including cognitive impairment. Rats fed with grape extracts accumulate 3′-O-methyl-quercetin-3-O-β-d-glucuronide (3) in their brains, suggesting 3 as a potential therapeutic agent. To develop methods for the synthesis of 3 and the related 4′-O-methyl-quercetin-7-O-β-d-glucuronide (4), 3-O-methyl-quercetin-3′-O-β-d-glucuronide (5), and 4′-O-methyl-quercetin-3′-O-β-d-glucuronide (6), which are not found in the brain, we have evaluated both enzymatic semisynthesis and full chemical synthetic approaches. Biocatalysis by mammalian UDP-glucuronosyltransferases generated multiple glucuronidated products from 4′-O-methylquercetin, and is not cost-effective. Chemical synthetic methods, on the other hand, provided good results; 3, 5, and 6 were obtained in six steps at 12, 18, and 30% overall yield, respectively, while 4 was synthesized in five steps at 34% overall yield. A mechanistic study on the unexpected regioselectivity observed in the quercetin glucuronide synthetic steps is also presented.

Effects of Functional Groups and Sugar Composition of Quercetin Derivatives on Their Radical Scavenging Properties

Quercetin derivatives are widespread in the plant kingdom and exhibit various biological actions. The aim of this study was to investigate the structure-activity relationships of quercetin derivatives, with a focus on the influence of functional groups and sugar composition on their antioxidant capacity. A series of quercetin derivatives were therefore prepared and assessed for their DPPH radical scavenging properties. Isoquercetin O-gallates were more potent radical scavengers than quercetin. The systematic analysis highlights the importance of the distribution of hydroxy substituents in isoquercetin O-gallates to their potency.