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Cardamonin

Cat No.:V17577 Purity: ≥98%
(E)-Cardamomin ((E)-Cardamomin) is a novel hTRPA1 cation channel antagonist (inhibitor) with IC50 of 454 nM.
Cardamonin
Cardamonin Chemical Structure CAS No.: 19309-14-9
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Other Forms of Cardamonin:

  • Cardamonin
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Top Publications Citing lnvivochem Products
Product Description
(E)-Cardamomin ((E)-Cardamomin) is a novel hTRPA1 cation channel antagonist (inhibitor) with IC50 of 454 nM.
Cardamonin (CAS 19309-14-9) is a naturally occurring chalcone, a type of polyphenol, found in the fruits of *Alpinia* species and other plants. It is a cell-permeable compound with a wide range of pharmacological activities, including potent anti-inflammatory, anticancer, and anti-melanogenic effects.
Biological Activity I Assay Protocols (From Reference)
Targets
Cardamonin targets multiple pathways. It is a novel antagonist of the human TRPA1 cation channel with an IC50 of 454 nM. It also inhibits the NF-κB pathway by suppressing p65NF-κB nuclear translocation and I-κBα phosphorylation. Additionally, it inhibits NO and PGE2 production.
ln Vitro
(E)-Cardamomomin does not interact with TRPV1 or TRPV4 channels, but instead preferentially inhibits TRPA1 activation (IC50=454 nM). Cardamomin's docking research indicated a compatible interaction with TRPA1's A-967079 binding site. (E)-Cardamomomin ((E)-Cardamomomin) did not significantly affect cardiomyocyte contraction or HEK293 cell viability [1]. Tgase-2, cyclooxygenase-2 (COX-2), and p65 (nuclear factor-κB) expression are all inhibited by (E)-Cardamomomin in a concentration-dependent manner, but IκB expression is restored in MG63 and Raw264.7 cells [2].
In vitro, Cardamonin (20, 40, and 80 mg/kg, intragastric) reduces inflammation in rats, demonstrating its systemic anti-inflammatory effects. It inhibits NO and PGE2 production from LPS- and IFN-γ-induced RAW cells and inhibits TXB2 production via the COX-1 and COX-2 pathways.
ln Vivo
(E)-Cardamomomin ((E)-Cardamomomin) (3-30 mg/kg, orally) dramatically reduces the writhing caused by PBQ. Additionally, carrageenan-induced hyperalgesia's withdrawal latency increases significantly in response to CDN in a dose-dependent manner [2].
In vivo, Cardamonin shows anti-inflammatory activity in various models. It inhibits NF-κB activation via inhibition of IκBα degradation and phosphorylation, IκB kinase activation, and NF-κB nuclear translocation. These effects contribute to its anticancer and anti-inflammatory properties.
Enzyme Assay
The in vitro receptor binding assay for Cardamonin involves measuring its antagonist activity at the hTRPA1 cation channel. This is typically performed using calcium flux assays in cells overexpressing the TRPA1 channel, where the compound's ability to block agonist-induced calcium influx is measured.
Cell Assay
In vitro cell-based assays are performed in RAW 264.7 macrophage cells. Cells are stimulated with LPS and IFN-γ to induce an inflammatory response. The production of NO and PGE2 is then measured in the presence and absence of Cardamonin to assess its anti-inflammatory activity.
Animal Protocol
In vivo activity is evaluated in animal models of inflammation, such as the rat model. Cardamonin is administered via intragastric gavage, and serum levels of pro-inflammatory molecules are measured to assess its systemic anti-inflammatory effect.
ADME/Pharmacokinetics
Pharmacokinetic properties of Cardamonin are not extensively detailed. As a natural product with oral activity (intragastric administration), it is likely absorbed and systemically distributed. Further studies would be needed to fully characterize its ADME profile.
Toxicity/Toxicokinetics
Detailed toxicological data for Cardamonin is not available in the standard research literature. As a naturally occurring compound with a history of use in traditional medicine, it is generally considered to have a low toxicity profile, but systematic studies are lacking.
References

[1]. Cardamonin, a Novel Antagonist of hTRPA1 Cation Channel, Reveals Therapeutic Mechanism of Pathological Pain. Molecules. 2016 Aug 29;21(9). pii: E1145.

[2]. Novel anti-nociceptive effects of cardamonin via blocking expression of cyclooxygenase-2 andtransglutaminase-2. Pharmacol Biochem Behav. 2014 Mar;118:10-5.

Additional Infomation
Cardamonin belongs to the chalcone class of compounds. Cardamonin (also known as dihydroxymethoxychalcone) has attracted considerable attention from the scientific community due to its health benefits, and the number of related publications is constantly increasing. The name Cardamonin comes from its presence in cardamom spices. Cardamonin has been reported to be found in Toona sinensis (Cedrelopsis grevei), turmeric (Boesenbergia rotunda), and other organisms with relevant data.
Cardamonin is a promising natural product lead for drug development, particularly for inflammatory diseases and cancer. Its multi-targeted mechanism of action, including TRPA1 antagonism and NF-κB inhibition, makes it a valuable tool for studying these pathways. It is not an approved drug.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C16H14O4
Molecular Weight
270.2800
Exact Mass
270.089
CAS #
19309-14-9
Related CAS #
Cardamonin; 18956-16-6; (E)-Cardamonin; 19309-14-9
PubChem CID
641785
Appearance
Light yellow to yellow solid powder
Density
1.3±0.1 g/cm3
Boiling Point
484.5±45.0 °C at 760 mmHg
Flash Point
182.7±22.2 °C
Vapour Pressure
0.0±1.3 mmHg at 25°C
Index of Refraction
1.658
Source
Originated from plants: Zingiberaceae Alpinia katsumadai Hayata
LogP
3.62
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
4
Heavy Atom Count
20
Complexity
346
Defined Atom Stereocenter Count
0
SMILES
COC1=CC(=CC(=C1C(=O)/C=C/C2=CC=CC=C2)O)O
InChi Key
NYSZJNUIVUBQMM-BQYQJAHWSA-N
InChi Code
InChI=1S/C16H14O4/c1-20-15-10-12(17)9-14(19)16(15)13(18)8-7-11-5-3-2-4-6-11/h2-10,17,19H,1H3/b8-7+
Chemical Name
(E)-1-(2,4-dihydroxy-6-methoxyphenyl)-3-phenylprop-2-en-1-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)
DMSO : ≥ 28 mg/mL (~103.60 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 15 mg/mL (55.50 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween-80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), Clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of DMSO stock solution (150.0 mg/mL) to 400 μL of PEG300 and mix well; then add 50 μL of Tween-80 and mix well; finally add 450 μL of physiological saline and adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.6999 mL 18.4993 mL 36.9987 mL
5 mM 0.7400 mL 3.6999 mL 7.3997 mL
10 mM 0.3700 mL 1.8499 mL 3.6999 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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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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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