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5,7,3',4'-Tetramethoxyflavone

Cat No.:V29073 Purity: ≥98%
5,7,3',4'-Tetramethoxyflavone is a polymethoxyflavone extracted from M.
5,7,3',4'-Tetramethoxyflavone
5,7,3',4'-Tetramethoxyflavone Chemical Structure CAS No.: 855-97-0
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
5,7,3',4'-Tetramethoxyflavone is a polymethoxyflavone extracted from M. exotica and has diverse biological effects like antifungal, antimalarial, antimycobacterial and anti~inflammatory activities. 5,7,3',4'-Tetramethoxyflavone exerts chondroprotective effects by targeting β-catenin.
5,7,3',4'-Tetramethoxyflavone (CAS 855-97-0) is a fully methoxylated polymethoxyflavone (PMF) belonging to the flavonoid class. It is naturally isolated from sources such as Murraya exotica and Kaempferia parviflora. This compound exhibits diverse biological activities. It selectively inhibits multidrug resistance. It also has antifungal, antimalarial, antimycobacterial, and anti-inflammatory activities. It exerts chondroprotective activity by targeting β-catenin signaling.
Biological Activity I Assay Protocols (From Reference)
Targets
5,7,3',4'-Tetramethoxyflavone targets multiple pathways. It selectively inhibits multidrug resistance. It exerts chondroprotective activity by targeting β-catenin signaling. It has antifungal, antimalarial, antimycobacterial, and anti-inflammatory activities. Its mechanism of action likely involves modulation of various signaling pathways, including those involved in inflammation, cell proliferation, and drug resistance.
ln Vitro
In vitro, 5,7,3',4'-Tetramethoxyflavone has antifungal, antimalarial, antimycobacterial, and anti-inflammatory activities. It selectively inhibits multidrug resistance. It exerts chondroprotective activity by targeting β-catenin signaling. Quantitative IC50 values for its activities are not detailed in the publicly available sources. These diverse in vitro activities make it a compound of interest for studying various disease models.
ln Vivo
In vivo activity data for 5,7,3',4'-Tetramethoxyflavone is limited in publicly available literature. As a compound with diverse biological activities in vitro, it is hypothesized to exhibit similar effects in vivo. Its chondroprotective activity suggests potential for in vivo studies in osteoarthritis models. Its anti-inflammatory and antimicrobial activities also suggest potential for in vivo efficacy studies. However, specific in vivo data, including pharmacokinetic and pharmacodynamic parameters, have not been detailed.
Enzyme Assay
For cell-free assays, the chondroprotective activity of 5,7,3',4'-Tetramethoxyflavone can be studied by measuring its effect on β-catenin signaling using reporter gene assays or by measuring the expression of β-catenin target genes. Its anti-inflammatory activity can be assessed by measuring its inhibition of inflammatory enzymes, such as COX-2 or LOX. Its antimicrobial activity can be assessed using standard broth microdilution methods to determine MIC values.
Cell Assay
For in vitro cellular assays, the chondroprotective activity of 5,7,3',4'-Tetramethoxyflavone can be assessed in chondrocyte cell lines. Cells are treated with the compound, and the expression of chondrogenic markers (e.g., collagen type II, aggrecan) and the inhibition of catabolic factors (e.g., MMP-13) are measured. Its anti-inflammatory activity is assessed in LPS-stimulated macrophages by measuring cytokine production. Its anticancer activity is assessed in cancer cell lines by measuring cell viability.
Animal Protocol
For in vivo studies, 5,7,3',4'-Tetramethoxyflavone could be administered orally in animal models of osteoarthritis, inflammation, or cancer. In osteoarthritis models, endpoints include cartilage degradation, pain, and joint inflammation. In inflammation models, endpoints include inflammatory cytokine levels and tissue histopathology. In cancer models, endpoints include tumor growth inhibition.
ADME/Pharmacokinetics
5,7,3',4'-Tetramethoxyflavone (CAS 855-97-0) has a molecular formula of C19H18O6 and a molecular weight of 342.34 g/mol. Its IUPAC name is 2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one. Purity is ≥98%. Appearance: A solid. Solubility: DMSO: Soluble; Methanol: Soluble. Storage: -20°C.
Toxicity/Toxicokinetics
No detailed toxicity data is publicly available. As a natural polymethoxyflavone from edible plants, it is generally considered to have low toxicity, but standard toxicological studies would be required for drug development. In vitro cytotoxicity assays in various cell lines are typically performed alongside efficacy studies to confirm that observed effects are not due to a general reduction in cell viability.
References

[1]. 5,7,3',4'-Tetramethoxyflavone exhibits chondroprotective activity by targeting β-catenin signaling in vivo and in vitro. Biochem Biophys Res Commun. 2014 Sep 26;452(3):682-8.

[2]. 5,7,3',4'-Tetramethoxyflavone protects chondrocytes from ER stress-induced apoptosis through regulation of the IRE1α pathway. Connect Tissue Res. 2018 Mar;59(2):157-166.

[3]. Absolute bioavailability, pharmacokinetics and excretion of 5,7,30 ,40 -tetramethoxyflavone.

Additional Infomation
3',4',5,7-Tetramethoxyflavonoids have been reported to be found in Boesenbergia rotunda, Citrus reticulata, and other organisms with available data.
5,7,3',4'-Tetramethoxyflavone is a research-grade compound and is not approved for therapeutic use. It serves primarily as a pharmacological tool for studying multidrug resistance, inflammation, and chondroprotection. Its mechanism of action involves modulation of β-catenin signaling and inhibition of inflammatory pathways. It is a natural product from Murraya exotica and Kaempferia parviflora. No clinical trials have been reported.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C19H18O6
Molecular Weight
342.3426
Exact Mass
342.11
CAS #
855-97-0
PubChem CID
631170
Appearance
White to off-white solid powder
Density
1.243g/cm3
Boiling Point
528.8ºC at 760 mmHg
Melting Point
195-197°C
Flash Point
233.9ºC
Index of Refraction
1.574
LogP
3.494
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
5
Heavy Atom Count
25
Complexity
504
Defined Atom Stereocenter Count
0
InChi Key
CLXVBVLQKLQNRQ-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H18O6/c1-21-12-8-17(24-4)19-13(20)10-15(25-18(19)9-12)11-5-6-14(22-2)16(7-11)23-3/h5-10H,1-4H3
Chemical Name
2-(3,4-dimethoxyphenyl)-5,7-dimethoxychromen-4-one
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)
DMSO : ~8.33 mg/mL (~24.33 mM)
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 2.9211 mL 14.6054 mL 29.2107 mL
5 mM 0.5842 mL 2.9211 mL 5.8421 mL
10 mM 0.2921 mL 1.4605 mL 2.9211 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.

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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?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
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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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  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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  • The answer appears in the Volume (to add to vial) box
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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