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Cirsimarin

Cat No.:V40576 Purity: ≥98%
Cirsimarin is a potent anti-lipid flavonoid extracted from Microtea debilis.
Cirsimarin
Cirsimarin Chemical Structure CAS No.: 13020-19-4
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
Other Sizes
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Product Description
Cirsimarin is a potent anti-lipid flavonoid extracted from Microtea debilis. Cirsimarin has potent anti-fat effects and reduces adipose tissue deposition in mice. The lipolytic activity of Cirsimarin is due to its antagonistic activity on adenosine A1 receptors and its inhibitory activity against phosphodiesterase.
Cirsimarin (CAS#: 13020-19-4) is a flavonoid glycoside isolated from Microtea debilis and other plants such as Cirsium japonicum. It has potent antilipogenic effects and decreases adipose tissue deposition in mice. Cirsimarin acts as an antagonist of the adenosine A1 receptor and inhibits phosphodiesterase. It is a potential candidate for the treatment of obesity. Its molecular formula is C23H24O11 with a molecular weight of 476.4 g/mol.
Biological Activity I Assay Protocols (From Reference)
Targets
Cirsimarin targets multiple pathways involved in lipid metabolism and inflammation. It acts as an antagonist of the adenosine A1 receptor, which is involved in the regulation of lipolysis and脂肪 accumulation. It also inhibits phosphodiesterase, an enzyme that breaks down cyclic nucleotides, leading to increased cAMP levels. These actions contribute to its antilipogenic effects and reduction of adipose tissue deposition.
ln Vitro
In vitro, cirsimarin has potent antilipogenic effects. It acts as an antagonist of the adenosine A1 receptor and inhibits phosphodiesterase. Its activity is typically evaluated using adipocyte differentiation assays, where lipid accumulation is measured by Oil Red O staining. Receptor binding assays are used to assess A1 receptor antagonism. Phosphodiesterase inhibition is measured using enzyme activity assays. However, specific IC50 values are not extensively reported.
ln Vivo
In vivo, cirsimarin decreases adipose tissue deposition in mice. It has potent antilipogenic effects. These properties make it a potential candidate for the treatment of obesity. However, specific in vivo efficacy data, including dosing regimens and animal models, are not extensively detailed in the available literature. Further studies are needed to fully characterize its in vivo pharmacological profile. The compound is a research tool for studying obesity and lipid metabolism.
Enzyme Assay
Cell-free assays for cirsimarin involve evaluating its adenosine A1 receptor antagonism and phosphodiesterase inhibition. Receptor binding assays are performed using membrane preparations expressing adenosine A1 receptors. Phosphodiesterase activity is measured using enzyme activity assays with cyclic nucleotide substrates. The compound's chemical purity and identity are confirmed by HPLC, NMR, and mass spectrometry. It is typically dissolved in DMSO for assay preparation.
Cell Assay
In vitro cellular assays for cirsimarin typically involve treating adipocytes or preadipocytes with various concentrations of the compound. Adipocyte differentiation is assessed by Oil Red O staining and measurement of adipogenic markers. Lipid accumulation is quantified. Receptor binding and phosphodiesterase inhibition are assessed in cell-based assays. The compound is typically dissolved in DMSO and diluted in cell culture medium.
Animal Protocol
In vivo animal studies for cirsimarin are conducted in mouse models of obesity. The compound is administered via various routes including oral gavage or intraperitoneal injection. Adipose tissue deposition is measured by weighing fat pads and histological analysis. Body weight and metabolic parameters are monitored. However, specific dosing regimens and experimental protocols are not extensively documented in the available literature. Standard protocols for evaluating anti-obesity agents would typically be employed.
ADME/Pharmacokinetics
Pharmacokinetic properties of cirsimarin include a molecular weight of 476.4 g/mol and molecular formula C23H24O11. As a flavonoid glycoside, it is expected to have moderate oral bioavailability. The compound is stable as a powder at -20°C for 3 years or at 4°C for 2 years; in solvent, it is stable at -80°C for 6 months or at -20°C for 1 month. Detailed ADME parameters are not extensively reported.
Toxicity/Toxicokinetics
The toxicity profile of cirsimarin has not been extensively characterized in published literature. As a natural flavonoid, it is generally considered to have a favorable safety profile at research doses. Standard preclinical safety studies would include acute and sub-chronic toxicity assessments in rodent models. The compound is intended for research use only and not for therapeutic applications in humans.
References

[1]. Cirsimarin, a potent antilipogenic flavonoid, decreases fat deposition in mice intra-abdominal adipose tissue. Int J Obes (Lond). 2010 Nov;34(11):1566-75.

Additional Infomation
Cirsimarin is a glycoside belonging to the flavonoid class of compounds. It has been reported to be found in Cirsium japonicum, Micrococcus pumila, and other organisms with relevant data.
Cirsimarin is a flavonoid glycoside with potent antilipogenic effects that decreases adipose tissue deposition in mice. It acts as an adenosine A1 receptor antagonist and inhibits phosphodiesterase. Its molecular formula is C23H24O11 with a molecular weight of 476.4 g/mol. Cirsimarin is a research tool for studying obesity and lipid metabolism. It is not for therapeutic use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C23H24O11
Molecular Weight
476.4301
Exact Mass
476.132
CAS #
13020-19-4
PubChem CID
159460
Appearance
Off-white to light yellow solid powder
Density
1.523g/cm3
Boiling Point
767.1ºC at 760 mmHg
Flash Point
265.8ºC
Vapour Pressure
9.47E-25mmHg at 25°C
Index of Refraction
1.657
LogP
0.361
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
11
Rotatable Bond Count
6
Heavy Atom Count
34
Complexity
736
Defined Atom Stereocenter Count
5
SMILES
COC1=C(C(=C2C(=C1)OC(=CC2=O)C3=CC=C(C=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)OC
InChi Key
RETJLKUBHXTIGH-FZFRBNDOSA-N
InChi Code
InChI=1S/C23H24O11/c1-30-15-8-14-17(19(27)22(15)31-2)12(25)7-13(33-14)10-3-5-11(6-4-10)32-23-21(29)20(28)18(26)16(9-24)34-23/h3-8,16,18,20-21,23-24,26-29H,9H2,1-2H3/t16-,18-,20+,21-,23-/m1/s1
Chemical Name
5-hydroxy-6,7-dimethoxy-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]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

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 2.0989 mL 10.4947 mL 20.9894 mL
5 mM 0.4198 mL 2.0989 mL 4.1979 mL
10 mM 0.2099 mL 1.0495 mL 2.0989 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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