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

TAMARIXETIN, also known as 4''-O-methyl Quercetin, is a flavonoid derived from the flavanoid Quercetin. It is a primary reference substance with assigned absolute purity and is produced by PhytoLab GmbH & Co. KG. TAMARIXETIN is isolated from Cyperus teneriffae and has been found to possess antioxidant properties, anticancer and antiplasmodial activity.

Uses

Used in Anticancer Applications:
TAMARIXETIN is used as an anticancer agent for its ability to inhibit the viability of various human tumor cell lines, including HL-60, U937, MOLT-3, Raji, K562, MCF-7, SK-MEL-1, and A549. It demonstrates this effect with IC50 values ranging from 5.5-24.1 μM and induces G2-M arrest and inhibits tubulin polymerization in vitro in a dose-dependent manner.
Additionally, TAMARIXETIN is used to inhibit breast cancer resistance protein (BCRP/ABCG2) with an IC50 of 40 nM in a vesicular transport assay, showing no cellular toxicity and indicating its potential for use in overcoming multidrug resistance in chemotherapy.
Used in Antimalarial Applications:
TAMARIXETIN is used as an antimalarial agent, reducing the in vitro proliferation of chloroquine-resistant P. falciparum with an IC50 of 4.8 μM. It also suppresses infection in mice, with 65-81% suppression at a 2.5-5 mg/kg dose.
Used in Cardioprotection:
TAMARIXETIN is used to protect H9c2 cardiomyoblasts against H2O2-induced oxidative stress by modulating PI3K/Akt and ERK1/2 signaling pathways, highlighting its potential use in the prevention and treatment of cardiovascular diseases.

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

• 480-66-0 2,4,6-trihydroxyacetophenone 
• 621-59-0 isovanillin 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 77-78-1 dimethyl sulfate 
• 153-18-4 rutin 
• 117-39-5 quercetol 
• 1197215-49-8 2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-5-hydroxy-3,7-bis(methoxymethoxy)-4H-chromen-4-one 
• 1197215-50-1 2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-bis(methoxymethoxy)-4H-chromen-4-one 
• 5779-98-6 O-methoxymethylisovanillin 
• 36804-11-2 2,4,6-tri-MOM phloracetophenone 
• 1334307-45-7 C₂₄H₃₀O₁₁ 
• 1334307-43-5 C₂₄H₃₀O₁₀ 
• 1268621-74-4 3',7-di-O-benzyl-4'-O-methylquercetin 
• 14265-53-3 Tamarixetin-7-O-rutinoside 

Downstream Products

• 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 
• 116097-15-5 C₁₆H₁₀O₁₃S₂^(2-)*2K⁽¹⁺⁾ 
• 116097-16-6 C₁₆H₉O₁₆S₃^(3-)*3K⁽¹⁺⁾ 
• 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.

Synthesis of Flavonols via Pyrrolidine Catalysis: Origins of the Selectivity for Flavonol versus Aurone

A novel synthetic method for flavonol from 2′-hydroxyl acetophenone and benzaldehyde promoted by pyrrolidine under an aerobic condition in water is established. This protocol was supported by efficient synthesis of 44 common examples and three natural products. The α, β-unsaturated iminium ion (enimine ion E) was proved to be the key intermediate in the reaction. H218O and 18O2 isotope tracking experiments demonstrated that both water and the aerobic atmosphere were necessary to ensure the transformation. The selectivity for flavonol or aurone was originated from solvent-triggered intermediates, which were determined by UV-visible spectra from isolated enimine. The phenol-iminium E-A is dominant in water and the ketoenamine intermediate E-B is prevalent in acetonitrile. In the presence of pyrrolidine and oxygen, E-A leads to flavonol through E-I, a zwitterionic-like phenoloxyl-iminium ion, following the key steps of cyclization and a [2 + 2] oxidation; E-B proceeds through path II, a radical process induced by photolysis of E-B with both pyrrolidine and oxygen, to afford aurone. Preliminary mechanistic studies are reported.

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.