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(R)-5,7-Dimethoxyflavanone

Cat No.:V55014 Purity: ≥98%
(R)-5,7-Dimethoxyflavanone showed strong antimutagenic activity against MeIQ mutagenesis of Typhimurium TA100 and TA98 strains in the Ames test, and also significantly and dose-dependently inhibited the inflammatory mediator: nitric oxide ( NO) and cytokines (TNF-α and IL-12).
(R)-5,7-Dimethoxyflavanone
(R)-5,7-Dimethoxyflavanone Chemical Structure CAS No.: 1277188-85-8
Product category: Apoptosis
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
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Product Description
(R)-5,7-Dimethoxyflavanone showed strong antimutagenic activity against MeIQ mutagenesis of Typhimurium TA100 and TA98 strains in the Ames test, and also significantly and dose-dependently inhibited the inflammatory mediator: nitric oxide ( NO) and cytokines (TNF-α and IL-12).
(R)-5,7-Dimethoxyflavanone (CAS 1277188-85-8) is a flavanone with the molecular formula C17H16O4 and a molecular weight of 284.31 g/mol. It is also known as (2R)-5,7-dimethoxyflavanone. The compound showed strong antimutagenic activity against MeIQ mutagenesis of Salmonella Typhimurium TA100 and TA98 strains in the Ames test. It also significantly and dose-dependently inhibited the inflammatory mediators nitric oxide (NO) and cytokines (TNF-α and IL-12).
Biological Activity I Assay Protocols (From Reference)
Targets
(R)-5,7-Dimethoxyflavanone targets inflammatory mediators, including nitric oxide (NO), TNF-α, and IL-12. By inhibiting these mediators, the compound exerts anti-inflammatory effects. The compound also has antimutagenic activity, as demonstrated in the Ames test. It is a flavanone with potential chemopreventive properties.
ln Vitro
In cell-free biochemical systems, (R)-5,7-Dimethoxyflavanone showed strong antimutagenic activity against MeIQ mutagenesis in the Ames test. The compound's antimutagenic activity is assessed using Salmonella Typhimurium strains TA100 and TA98. Its ability to inhibit inflammatory mediators can be evaluated in cell-based systems.
ln Vivo
In cell-based assays, (R)-5,7-Dimethoxyflavanone significantly and dose-dependently inhibits the inflammatory mediators nitric oxide (NO) and cytokines (TNF-α and IL-12). The compound's anti-inflammatory effects are evaluated in immune cells such as macrophages. It also showed strong antimutagenic activity in the Ames test.
Enzyme Assay
The cell-free assay for (R)-5,7-Dimethoxyflavanone involves the Ames test to assess antimutagenic activity. Salmonella Typhimurium strains TA100 and TA98 are used with MeIQ as the mutagen. The compound is tested at various concentrations to determine its ability to inhibit mutagenesis. The compound's ability to scavenge free radicals can be assessed using DPPH or ABTS assays.
Cell Assay
Cell-based assays for (R)-5,7-Dimethoxyflavanone involve culturing immune cells such as macrophages and treating them with the compound at concentrations ranging from 0.1 to 100 μM. Cells are stimulated with LPS to induce the production of inflammatory mediators. Nitric oxide (NO) levels are measured using the Griess assay. TNF-α and IL-12 levels in the supernatant are measured by ELISA.
Animal Protocol
There is no established animal experimental protocol for (R)-5,7-Dimethoxyflavanone specifically. As an anti-inflammatory and antimutagenic compound, it could potentially be evaluated in animal models of inflammation or mutagenesis. Typical studies involve administration of the compound to mice via oral or intraperitoneal routes. Inflammatory markers and DNA damage are assessed.
ADME/Pharmacokinetics
Pharmacokinetic properties of (R)-5,7-Dimethoxyflavanone have not been extensively reported. As a small molecule with a molecular weight of 284.31 g/mol, the compound would be expected to have moderate oral bioavailability and tissue penetration. The compound is soluble in DMSO. Further pharmacokinetic studies would be required to determine plasma half-life, clearance, and metabolic pathways.
Toxicity/Toxicokinetics
(R)-5,7-Dimethoxyflavanone is intended for research use only and lacks established toxicity profiles for therapeutic applications. Standard laboratory safety precautions should be observed when handling this compound. As an anti-inflammatory compound, it may have effects on immune function. Standard toxicity studies in rodents would be required to determine the safety profile.
References

[1]. Okuno Y, Marumoto S, Miyazawa M. Antimutagenic activity of flavonoids from Sozuku. Nat Prod Res. 2019;33(6):862-865.

[2]. Rao YK, Fang SH, Tzeng YM. Anti-inflammatory activities of flavonoids isolated from Caesalpinia pulcherrima. J Ethnopharmacol. 2005;100(3):249-253.

Additional Infomation
(R)-5,7-Dimethoxyflavanone is a research-grade compound supplied for anti-inflammatory and antimutagenic research. It is not an approved pharmaceutical and has no clinical trial history. The compound is a flavanone with antimutagenic and anti-inflammatory activities. This product is intended for research use only and is not for human therapeutic applications.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C17H16O4
Molecular Weight
284.31
Exact Mass
284.105
CAS #
1277188-85-8
PubChem CID
689012
Appearance
White to off-white solid powder
LogP
3.41
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
3
Heavy Atom Count
21
Complexity
364
Defined Atom Stereocenter Count
1
SMILES
O1C2C=C(C=C(C=2C(C[C@@H]1C1C=CC=CC=1)=O)OC)OC
InChi Key
IAFBOKYTDSDNHV-CQSZACIVSA-N
InChi Code
InChI=1S/C17H16O4/c1-19-12-8-15(20-2)17-13(18)10-14(21-16(17)9-12)11-6-4-3-5-7-11/h3-9,14H,10H2,1-2H3/t14-/m1/s1
Chemical Name
(2R)-5,7-dimethoxy-2-phenyl-2,3-dihydrochromen-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: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
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 3.5173 mL 17.5864 mL 35.1729 mL
5 mM 0.7035 mL 3.5173 mL 7.0346 mL
10 mM 0.3517 mL 1.7586 mL 3.5173 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

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
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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)
  • Click the “Calculate” button
  • 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:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • 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)
  • Click the “Calculate” button
  • 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:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
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.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • 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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