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Jaranol

Alias: Kamatakenin; Kumatakillin; Jaranol
Cat No.:V22844 Purity: ≥98%
Kumatakenin is a natural flavonoid extracted from cloves and has the effect of inducing apoptosis in ovarian cancer/tumor cells.
Jaranol
Jaranol Chemical Structure CAS No.: 3301-49-3
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
Kumatakenin is a natural flavonoid extracted from cloves and has the effect of inducing apoptosis in ovarian cancer/tumor cells.
Jaranol (CAS#: 3301-49-3), also known as Kumatakenin or Kaempferol 3,7-dimethyl ether, is a natural O-methylated flavonol found in various plants including cloves (Syzygium aromaticum). It has the effect of inducing apoptosis in ovarian cancer cells. Jaranol exhibits diverse biological activities and has been studied for its potential therapeutic applications. The compound is also known as 4',5-dihydroxy-3,7-dimethoxyflavone and has the molecular formula C17H14O6.
Biological Activity I Assay Protocols (From Reference)
Targets
Jaranol does not have a single defined pharmacological target. As a flavonoid, it likely interacts with multiple cellular targets to exert its biological activities. Jaranol has been shown to induce apoptosis in ovarian cancer cells, suggesting involvement in pro-apoptotic signaling pathways. The compound may modulate cell cycle regulation, inhibit proliferation, and activate cell death pathways. As a kaempferol derivative, it may share some of the biological activities of kaempferol, including antioxidant, anti-inflammatory, and anti-cancer properties. However, the specific molecular targets have not been fully characterized.
ln Vitro
In vitro, Jaranol inhibits the growth of SKOV3 ovarian cancer cells. It induces apoptosis in ovarian cancer cells, demonstrating anti-cancer activity. As a flavonoid, Jaranol would be expected to exhibit antioxidant activity through free radical scavenging and metal chelation. However, specific IC50 values or detailed activity data is not provided in the available sources. The compound's diverse biological activities make it a valuable tool for studying cancer biology and natural product pharmacology.
ln Vivo
In vivo, Jaranol has been studied for its potential therapeutic applications. As an apoptosis-inducing compound, it would be expected to have anti-tumor activity in animal models. However, specific in vivo efficacy data from animal models is not detailed in the available sources. The compound's natural occurrence in cloves and other plants suggests it may have a favorable safety profile at dietary levels. Comprehensive in vivo studies would be required for therapeutic development.
Enzyme Assay
For apoptosis-inducing compounds, standard cell-free assays include caspase activity assays using fluorogenic substrates, and assessment of mitochondrial membrane potential using fluorescent dyes. For antioxidant activity, standard cell-free assays include DPPH radical scavenging, ABTS radical cation decolorization, and ferric reducing antioxidant power (FRAP) assays.
Cell Assay
For apoptosis-inducing compounds, standard cellular assays involve treatment of cancer cell lines (e.g., SKOV3 ovarian cancer cells) with the test compound for 24-72 hours. Apoptosis is assessed by Annexin V/PI staining, caspase activity assays, and DNA fragmentation. Cell viability is measured using MTT or CellTiter-Glo assays to determine IC50 values. Cell cycle analysis is performed by flow cytometry.
Animal Protocol
For in vivo evaluation of anti-cancer compounds, standard animal models include tumor xenograft models using cancer cell lines sensitive to the compound. The compound is typically administered orally or intraperitoneally for 2-4 weeks. Tumor growth, apoptosis markers, and survival are assessed. For Jaranol, specific in vivo protocols have not been detailed in the available sources.
ADME/Pharmacokinetics
Detailed pharmacokinetic data for Jaranol is not provided in the available sources. The compound has a molecular weight of 314.29 and formula C17H14O6. As a flavonoid with moderate lipophilicity, it would be expected to have reasonable oral absorption. Comprehensive pharmacokinetic studies would be required for therapeutic development.
Toxicity/Toxicokinetics
Detailed toxicology data for Jaranol is not provided in the available sources. As a naturally occurring flavonoid found in cloves and other plants, it may have a favorable safety profile at moderate doses. However, comprehensive toxicological evaluation would be required for therapeutic development. The compound is for research use only and not for therapeutic applications.
References

[1]. Steroidal alkaloid glycosides from Solanum suaveolens.Phytochemistry. 1997 Dec;46(7):1279-82.

Additional Infomation
Kumatakenin is a flavonoid compound belonging to the ether class of compounds. It has been reported to exist in Melicope semecarpifolia, Osyris alba, and other organisms with relevant data. See also: Glycyrrhiza glabra (partial); Glycyrrhiza uralensis Root (partial).
Jaranol is also known as Kumatakenin, Kaempferol 3,7-dimethyl ether, 3,7-Di-O-methylkaempferol, and 4',5-dihydroxy-3,7-dimethoxyflavone. It has the UNII code 5FAQ11412T. The compound is a natural flavonoid extracted from cloves that induces apoptosis in ovarian cancer cells. No regulatory approval has been identified.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C17H14O6
Molecular Weight
314.29
Exact Mass
314.079
CAS #
3301-49-3
PubChem CID
5318869
Appearance
Light yellow to green yellow solid powder
Density
1.5±0.1 g/cm3
Boiling Point
578.4±50.0 °C at 760 mmHg
Flash Point
217.4±23.6 °C
Vapour Pressure
0.0±1.7 mmHg at 25°C
Index of Refraction
1.671
LogP
2.79
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
3
Heavy Atom Count
23
Complexity
480
Defined Atom Stereocenter Count
0
InChi Key
BJBUTJQYZDYRMJ-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H14O6/c1-21-11-7-12(19)14-13(8-11)23-16(17(22-2)15(14)20)9-3-5-10(18)6-4-9/h3-8,18-19H,1-2H3
Chemical Name
5-hydroxy-2-(4-hydroxyphenyl)-3,7-dimethoxychromen-4-one
Synonyms
Kamatakenin; Kumatakillin; Jaranol
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 3.1818 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.

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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)
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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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  • 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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