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Ladanein

Ladanein is a natural flavonoid extracted from Thymus piperella.
Ladanein
Ladanein Chemical Structure CAS No.: 10176-71-3
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
Ladanein is a natural flavonoid extracted from Thymus piperella.
Ladanein (CAS#: 10176-71-3) is a naturally occurring flavonoid compound found in various plants, particularly in the genus Ladanum and isolated from Thymus piperella. It is a dimethoxyflavone that is scutellarein in which the hydroxy groups at positions 4' and 7 are replaced by methoxy groups. Ladanein has gained attention for its antioxidant, anti-inflammatory, and potential anticancer properties. It is also an effective anti-HCV agent and has been identified as a potent antiviral drug against hepatitis C virus (HCV).
Biological Activity I Assay Protocols (From Reference)
Targets
Ladanein targets the hepatitis C virus (HCV) by disrupting the interactions of core and other HCV proteins. It is a phytochemicals inhibitor that interferes with HCV replication. As a flavonoid, ladanein may also interact with multiple molecular targets involved in inflammation and oxidative stress, such as enzymes and signaling pathways like NF-κB, MAPK, and PI3K/Akt. It can also act as an antioxidant by scavenging free radicals and chelating metal ions.
ln Vitro
In vitro, ladanein is an effective anti-HCV agent. It is a phytochemicals inhibitor that is known to disrupt the interactions of core and other hepatitis C virus (HCV) proteins. As a flavonoid, it is expected to exhibit antioxidant and anti-inflammatory activities. However, specific IC50 values for its antiviral or other activities are not detailed in the available literature. In cell-based assays, ladanein can inhibit HCV replication in infected cells.
ln Vivo
In vivo, ladanein has been studied for its potential antiviral effects against HCV. However, specific in vivo data are not detailed in the available literature. As a flavonoid, it may have limited oral bioavailability due to its sugar moiety, but it could be hydrolyzed to its aglycone form in the gastrointestinal tract. Further studies are needed to determine its pharmacokinetic and pharmacodynamic properties in animal models.
Enzyme Assay
Non-cellular in vitro assays for ladanein involve studying its antiviral activity against HCV. A typical protocol uses an HCV replicon system or a cell-free assay to measure the inhibition of HCV protein interactions or replication. The compound is incubated with HCV proteins or RNA, and the inhibition of replication or protein-protein interactions is measured. Alternatively, its antioxidant activity can be measured using cell-free assays such as DPPH radical scavenging or ABTS assays, where the compound is incubated with the radical solution and the decrease in absorbance is measured spectrophotometrically.
Cell Assay
Cellular assays for ladanein are performed using HCV-infected cell lines or hepatocytes. Cells are treated with ladanein at various concentrations for 24-72 hours. HCV replication is measured by quantifying HCV RNA by RT-PCR or by measuring HCV core protein levels by ELISA. Cell viability is measured using an MTT assay to ensure that the observed effects are not due to cytotoxicity. The IC50 for inhibition of HCV replication is determined.
Animal Protocol
In vivo animal studies for ladanein are conducted in mouse models of HCV infection, such as humanized mouse models or transgenic mice expressing HCV proteins. Animals are administered ladanein orally or intraperitoneally at doses such as 10-50 mg/kg. Viral load is measured in blood and liver tissues. Liver histology is examined to assess the effects on inflammation and fibrosis. However, specific published protocols for ladanein are limited in the available literature.
ADME/Pharmacokinetics
Ladanein has a molecular formula of 5,6-dihydroxy-7,4'-dimethoxyflavone and is soluble in chloroform, dichloromethane, ethyl acetate, DMSO, and acetone. It is a solid powder that should be stored desiccated at -20°C. Its molecular weight is not specified in the available literature. Detailed pharmacokinetic parameters have not been reported.
Toxicity/Toxicokinetics
Detailed toxicological data for ladanein have not been extensively reported. As a natural product used for research, it is generally considered to have low toxicity, but comprehensive safety data are not available. Standard laboratory safety precautions should be followed when handling ladanein. It is not a drug and is not intended for human use.
References

[1]. Highly Methylated 6-Hydroxyflavones and Other Flavonoids from Thymus piperella. Planta Med. 1985;51(5):452-454.

Additional Infomation
Latanine is a dimethoxyflavonoid, a derivative of baicalin, with its 4' and 7' hydroxyl groups replaced by methoxy groups. It is a potent antiviral drug against hepatitis C virus (HCV). Latanine has applications as a plant metabolite, antiviral agent, and free radical scavenger. It is a dimethoxyflavonoid and a dihydroxyflavonoid, functionally related to baicalin. Latanine has been reported in bees (Apis), peppermint (Nepeta pungens), and several other organisms with relevant data.
Ladanein is a naturally occurring flavonoid compound found in various plants, particularly in the genus Ladanum and isolated from Thymus piperella. It is a dimethoxyflavone (5,6-dihydroxy-7,4'-dimethoxyflavone) that is an effective anti-HCV agent. It disrupts the interactions of core and other hepatitis C virus (HCV) proteins. Ladanein has also gained attention for its antioxidant, anti-inflammatory, and potential anticancer properties. It is not a clinically approved drug and has not entered clinical trials. Its primary value is as a research tool for natural product chemistry and antiviral research.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C17H14O6
Molecular Weight
314.28946
Exact Mass
314.079
CAS #
10176-71-3
Related CAS #
10176-71-3;
PubChem CID
3084066
Appearance
Light yellow to yellow solid powder
Density
1.4±0.1 g/cm3
Boiling Point
565.7±50.0 °C at 760 mmHg
Melting Point
310-313℃
Flash Point
212.4±23.6 °C
Vapour Pressure
0.0±1.6 mmHg at 25°C
Index of Refraction
1.646
LogP
3.49
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
3
Heavy Atom Count
23
Complexity
468
Defined Atom Stereocenter Count
0
InChi Key
UUQJTIHOVGMQIH-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H14O6/c1-21-10-5-3-9(4-6-10)12-7-11(18)15-13(23-12)8-14(22-2)16(19)17(15)20/h3-8,19-20H,1-2H3
Chemical Name
5,6-dihydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-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

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 3.1818 mL 15.9089 mL 31.8177 mL
5 mM 0.6364 mL 3.1818 mL 6.3635 mL
10 mM 0.3182 mL 1.5909 mL 3.1818 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
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
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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