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Cynarin

Cat No.:V19003 Purity: ≥98%
Cynarin is an anti-asphyxiant with diverse biological effects like antioxidant, antihistamine and anti-viral effects.
Cynarin
Cynarin Chemical Structure CAS No.: 30964-13-7
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
50mg
Other Sizes

Other Forms of Cynarin:

  • 1,3-Dicaffeoylquinic acid
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Cynarin is an anti-asphyxiant with diverse biological effects like antioxidant, antihistamine and anti-viral effects.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Water becomes sweeter when cynarin suppresses taste receptors. Numerous pharmacological characteristics, such as cholesterol-lowering, hepatoprotective, antiviral, antibacterial, and antihistamine actions, have been demonstrated. Significant antioxidant, anticholinergic, reducing, free radical scavenging, and metal binding properties are exhibited by cynarin. At 30 mg/mL, cynarin prevents 87.72% of linoleic acid lipid peroxidation. Effective scavenging of DMPD+, ABTS+, O2-, DPPH1, and H2O2 as well as Fe2+ chelation and reduction are features of cynarin. Cynarin inhibits acetylcholinesterase with an IC50 of 243.67 nM and a Ki of 39.34±13.88 nM, respectively [1]. Potential immunosuppressant cynarin inhibits the interaction between antigen-presenting cells' CD80 and CD28 T cell receptors. Cynarin inhibits approximately 87% of the CD28-dependent "Signal 2" pathway that T cells activate when there is a one-to-one ratio of T cells to B cells. The interaction location between CD28 and CD80 is disrupted when cynarin binds to CD28's "G pocket" [2].
References

[1]. Antioxidant, antiradical, and anticholinergic properties of cynarin purified from the Illyrian thistle (Onopordum illyricum L.). J Enzyme Inhib Med Chem. 2016;31(2):266-75.

[2]. Blocking effect of an immuno-suppressive agent, cynarin, on CD28 of T-cell receptor. Pharm Res. 2009 Feb;26(2):375-81.

Additional Infomation
1,3-dicaffeoylquinic acid is an alkyl caffeate ester obtained by the formal condensation of hydroxy groups at positions 1 and 3 of ()-quinic acid with two molecules of trans-caffeic acid. It has a role as a plant metabolite. It is a quinic acid and an alkyl caffeate ester. It is functionally related to a trans-caffeic acid and a (-)-quinic acid. It is a conjugate acid of a 1,3-dicaffeoylquinate.
Cynarine has been reported in Echinacea angustifolia, Solanum tuberosum, and other organisms with data available.
See also: Cynara scolymus leaf (part of).
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C25H24O12
Molecular Weight
516.451
Exact Mass
516.126
CAS #
30964-13-7
Related CAS #
1,3-Dicaffeoylquinic acid;19870-46-3
PubChem CID
5281769
Appearance
White to light yellow solid powder
Density
1.6±0.1 g/cm3
Boiling Point
819.9±65.0 °C at 760 mmHg
Melting Point
225-227 °C
Flash Point
278.1±27.8 °C
Vapour Pressure
0.0±3.1 mmHg at 25°C
Index of Refraction
1.719
LogP
1.64
Hydrogen Bond Donor Count
7
Hydrogen Bond Acceptor Count
12
Rotatable Bond Count
9
Heavy Atom Count
37
Complexity
887
Defined Atom Stereocenter Count
4
SMILES
C1[C@H]([C@@H]([C@@H](C[C@]1(C(=O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)OC(=O)/C=C/C3=CC(=C(C=C3)O)O)O)O
InChi Key
YDDUMTOHNYZQPO-RVXRWRFUSA-N
InChi Code
InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1
Chemical Name
(1R,3R,4S,5R)-1,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxycyclohexane-1-carboxylic acid
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)
DMSO : ≥ 23 mg/mL (~44.53 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 1.9363 mL 9.6815 mL 19.3630 mL
5 mM 0.3873 mL 1.9363 mL 3.8726 mL
10 mM 0.1936 mL 0.9681 mL 1.9363 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.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT05686993 Active,not recruiting Drug: Cinnarizine
Drug: NIFEdipine ER
Primary Aldosteronism
Endocrine Hypertension
Queen Mary
University of London
May 5, 2023 Not Applicable
NCT00065715 Completed Dietary Supplement:Echinacea
Other: Blinded placebo
Common Cold University of
Wisconsin, Madison
September 2003 Phase 3
Biological Data
  • AFTIR scheme. The compound cynarin was discovered in Echinacea extract by the AFTIR method. This schematic diagram shows the immobilization of CD28 (extra-cellular part) in the chip. Many components from the extract of Echinacea purpurea, including cynarin, are indicated by different symbols flowing across the immobilized CD28. Subsequently, only cynarin is bound to the specific binding site of CD28, and other components are washed off the chip. Pharm Res. 2009 Feb;26(2):375-81.
  • G-pocket of CD28 appeared to be the most probable binding site for cynarin. Spatial locations of cynarin on CD28 were predicted with 100 runs of global docking analysis using AutoDock. A 3-D structure of CD28 with 100 superimposed cynarin predicted to be docked onto the receptor. The yellow arrow indicates the location of G-pocket. The spheres indicate the center-of-mass of a cynarin molecule. The calculated docked energies were presented with a red-to-blue gradient. Red indicated the lowest docked energy (i.e. −11.5 kcal/mol in this study and suggesting the most probable conformation) while blue shows the highest (i.e. −4.95 kcal/mol). B A 3D scatter plot to show the binding location on CD28 for each of the 100 predicted cynarin binding. The yellow arrow indicates the location of G-pocket. The majority of the predicted cynarin bindings were clustered at the G-pocket of CD28 with relatively lower docked energies than the rest.Pharm Res. 2009 Feb;26(2):375-81.
  • IC50 on co-stimulated (signal 1+signal 2) of T-cell activation and cytotoxicity of cynarin. The reductions of IL-2 production by T-cells as a function of concentration of cynarin was plotted by route 1 (R1) (anti-CD3+anti-CD28; filled squares) and route 2 (R2) (anti-CD3+B-cell; curve represented by open circles). There was little cytotoxicity seen in T-cells at all concentrations of cynarin used, up to 1,000 μg/mL (MTT assay; represented by filled triangles). The experiments were repeated four times and the average value and error in average were shown. Pharm Res. 2009 Feb;26(2):375-81.
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