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3',4',7-Trimethoxyquercetin (Quercetin 3',4',7-trimethyl ether)

Alias: Quercetin 3′,4′,7-trimethyl ether; 3',4',7-Trimethoxyquercetin
Cat No.:V62353 Purity: ≥98%
3',4',7-Trimethoxyquercetin (Quercetin 3',4',7-trimethyl ether) is a polymethoxyflavonoid extracted from Scutellaria baicalensis and has anti-oxidant effect.
3',4',7-Trimethoxyquercetin (Quercetin 3',4',7-trimethyl ether)
3',4',7-Trimethoxyquercetin (Quercetin 3',4',7-trimethyl ether) Chemical Structure CAS No.: 6068-80-0
Product category: Phenols
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
Other Sizes
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Product Description
3',4',7-Trimethoxyquercetin (Quercetin 3',4',7-trimethyl ether) is a polymethoxyflavonoid isolated from Scutellaria baicalensis and has antioxidant activity.
3',4',7-Trimethoxyquercetin (Quercetin 3',4',7-trimethyl ether, CAS# 6068-80-0) is a polymethoxylated flavone with the molecular formula C18H16O7 and a molecular weight of 344.32. It can be isolated from medicinal plants including Taraxacum mongolicum and Scutellaria baicalensis. As a methylated flavonol derivative of quercetin, the methoxy groups at the 3', 4', and 7 positions confer increased lipophilicity and metabolic stability compared to the parent compound. 3',4',7-Trimethoxyquercetin displays a range of pharmacological activities including antioxidant, anti-inflammatory, anticancer, and neuroprotective effects. It is a derivative of quercetin hydrate and has demonstrated anti-tumor activity in research models. The compound is intended for research use only and is not for human therapeutic use.
Biological Activity I Assay Protocols (From Reference)
Targets
3',4',7-Trimethoxyquercetin modulates key signaling pathways including NF-κB and PI3K/Akt, contributing to cellular protection and immune regulation. It also modulates the MAPK/ERK pathway, which is crucial for cell proliferation and differentiation. As a polymethoxyflavonoid, its targets include inflammatory mediators such as IL-6, with demonstrated suppression of LPS-induced IL-6 production in mouse J774.A1 cells. The compound's antioxidant activity involves scavenging free radicals and reducing oxidative stress in cellular models. Its anticancer activity is mediated through modulation of survival and proliferation pathways. The compound's increased lipophilicity due to methylation may enhance its interactions with cellular membranes and targets.
ln Vitro
In vitro studies have demonstrated that 3',4',7-Trimethoxyquercetin exhibits anti-inflammatory activity in mouse J774.A1 cells with an IC50 of 22.9 μM for suppression of LPS-induced IL-6 production as measured by ELISA. At concentrations of 1-10 μM for 3 hours, the compound shows activity in MCF-7 breast cancer cells. The compound displays antioxidant properties through free radical scavenging mechanisms. Its anticancer activity has been demonstrated in various cancer cell lines. The compound's ability to modulate NF-κB and PI3K/Akt pathways contributes to its anti-inflammatory and cytoprotective effects in vitro. These in vitro findings support its potential in therapeutic and nutraceutical development.
ln Vivo
In vivo studies of 3',4',7-Trimethoxyquercetin are limited as the compound is primarily used as a research chemical. As a methylated flavonol derivative, it is expected to have enhanced metabolic stability and bioavailability compared to quercetin, potentially allowing for better systemic exposure in vivo. The compound's anti-inflammatory and antioxidant activities suggest potential for in vivo evaluation in models of inflammation and oxidative stress. Its anticancer activity indicates potential for evaluation in tumor models. However, comprehensive in vivo pharmacological studies are not well documented in the available literature. The compound is intended for research use only and is not for human therapeutic use.
Enzyme Assay
In vitro enzyme/receptor binding assays for 3',4',7-Trimethoxyquercetin typically involve testing its anti-inflammatory activity through suppression of LPS-induced IL-6 production. Mouse J774.A1 cells are stimulated with LPS and treated with varying concentrations of the compound (with an IC50 of 22.9 μM), and IL-6 levels are measured by ELISA. For antioxidant activity, cell-free systems such as DPPH radical scavenging assays, ABTS assays, or ferric reducing antioxidant power (FRAP) assays are employed. Kinase inhibition assays may be performed to evaluate modulation of NF-κB, PI3K/Akt, and MAPK/ERK pathways. All assays are performed with appropriate controls and standardized protocols to ensure reproducibility of results.
Cell Assay
In vitro cell-based assays for 3',4',7-Trimethoxyquercetin involve culturing cell lines such as mouse J774.A1 macrophages to evaluate anti-inflammatory activity. Cells are treated with varying concentrations of the compound (1-10 μM for 3 hours) and stimulated with LPS. IL-6 production is measured by ELISA. For anticancer studies, cancer cell lines such as MCF-7 are treated with the compound and cell viability is assessed using MTT or similar colorimetric assays. Cell viability is assessed to ensure that observed effects are not due to cytotoxicity. All experiments are performed in triplicate with appropriate controls to ensure statistical reliability.
Animal Protocol
In vivo animal experiments for 3',4',7-Trimethoxyquercetin would be conducted to evaluate its anti-inflammatory, antioxidant, and anticancer activities. For anti-inflammatory studies, animals with induced inflammation would be treated with the compound and inflammatory markers measured. For antioxidant studies, animals would be administered the compound and markers of oxidative stress measured in blood and tissue samples. For anticancer studies, tumor-bearing animals would be treated and tumor growth monitored. Parameters assessed would include body weight, organ weights, inflammatory markers, and histopathology. Control groups receiving vehicle alone would be included for comparison. All procedures would comply with institutional animal care and use committee guidelines. Comprehensive in vivo studies are not well documented in the available literature.
ADME/Pharmacokinetics
The pharmacokinetic properties of 3',4',7-Trimethoxyquercetin reflect its nature as a methylated flavonol derivative. It has a molecular weight of 344.32 and the molecular formula C18H16O7. The methoxy groups at the 3', 4', and 7 positions confer increased lipophilicity and metabolic stability compared to quercetin, which may enhance oral absorption and systemic bioavailability. The compound is expected to be metabolized through standard xenobiotic pathways in the liver, including demethylation and conjugation reactions. Complete pharmacokinetic profiling including half-life, clearance, volume of distribution, and bioavailability would require further systematic studies using appropriate analytical methods such as high-performance liquid chromatography-mass spectrometry.
Toxicity/Toxicokinetics
The toxicity profile of 3',4',7-Trimethoxyquercetin has been evaluated in the context of its use as a research chemical. As a methylated flavonol derivative of quercetin, it is expected to have a favorable safety profile at research concentrations. The compound's anti-inflammatory and antioxidant activities suggest potential for beneficial effects. However, as with all research chemicals, proper handling procedures including use of personal protective equipment are recommended. The compound is not approved for human therapeutic use and is intended for research purposes only. Long-term toxicity studies would be needed to fully establish its safety profile for pharmaceutical applications.
References

[1]. A high-speed counter-current chromatography- HPLC-DAD method for preparative isolation and purification of two polymethoxylated flavones from Taraxacum mongolicum. J Chromatogr Sc . May-Jun 2009;47(5):349-53.

Additional Infomation
Quercetin 7,3',4'-trimethyl ether is a trimethoxyflavonoid, a 7,3',4'-trimethyl ether derivative of quercetin. It has been isolated from Euodia confusa. It is both a metabolite and a plant metabolite. It is a dihydroxyflavonoid, belonging to the flavonol, trimethoxyflavon, and 3'-methoxyflavonoid classes. Its function is related to that of quercetin. Quercetin 7,3',4'-trimethyl ether has also been reported in Aeonium arboreum, Viscum coloratum, and several other organisms with relevant data.
3',4',7-Trimethoxyquercetin (CAS# 6068-80-0) is also known as Quercetin 3',4',7-trimethyl ether and 2-(3,4-dimethoxyphenyl)-3,5-dihydroxy-7-methoxychromen-4-one. It has a purity of ≥95%. The compound is a polymethoxyflavonoid that can be isolated from Taraxacum mongolicum and Scutellaria baicalensis. It is a derivative of quercetin hydrate and exhibits anti-tumor activity. The compound modulates key signaling pathways including NF-κB, PI3K/Akt, and MAPK/ERK. It displays antioxidant, anti-inflammatory, anticancer, and neuroprotective effects. The compound is intended for research use only and is not for human therapeutic use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C18H16O7
Molecular Weight
344.32
Exact Mass
344.09
CAS #
6068-80-0
PubChem CID
5748558
Appearance
White to off-white solid
LogP
2.897
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
7
Rotatable Bond Count
4
Heavy Atom Count
25
Complexity
532
Defined Atom Stereocenter Count
0
SMILES
COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)OC)O)O)OC
InChi Key
OEEUHNAUMMATJT-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H16O7/c1-22-10-7-11(19)15-14(8-10)25-18(17(21)16(15)20)9-4-5-12(23-2)13(6-9)24-3/h4-8,19,21H,1-3H3
Chemical Name
2-(3,4-dimethoxyphenyl)-3,5-dihydroxy-7-methoxychromen-4-one
Synonyms
Quercetin 3′,4′,7-trimethyl ether; 3',4',7-Trimethoxyquercetin
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.9043 mL 14.5214 mL 29.0428 mL
5 mM 0.5809 mL 2.9043 mL 5.8086 mL
10 mM 0.2904 mL 1.4521 mL 2.9043 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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