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Chelidonic acid

Cat No.:V28583 Purity: ≥98%
Chelidonic acid is an acid substance extracted from Chelidonium majus L.
Chelidonic acid
Chelidonic acid Chemical Structure CAS No.: 99-32-1
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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500mg
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Product Description
Chelidonic acid is an acid substance extracted from Chelidonium majus L. and is an anti-bacterial agent. Chelidonic acid has anti~inflammatory effects and may reduce IL-6 production by inhibiting NF-κB and caspase-1. Chelidonic acid is a glutamate decarboxylase inhibitor (antagonist) with Ki of 1.2 μM.
Chelidonic acid is a naturally occurring organic acid found in the plant Chelidonium majus (greater celandine) and other plants. It is a γ-pyrone derivative that is structurally related to meconic acid. Chelidonic acid has been studied for its various pharmacological activities, including anti-inflammatory, analgesic, antimicrobial, and hepatoprotective effects. The compound is also a known inhibitor of certain enzymes and has been investigated for its potential therapeutic applications. It is primarily used in research as a natural product and biochemical tool.
Biological Activity I Assay Protocols (From Reference)
Targets
Chelidonic acid does not have a specific drug target but acts through multiple mechanisms. It has been shown to inhibit the activity of various enzymes, including phospholipase A2 and certain kinases. The compound has anti-inflammatory effects by inhibiting the production of pro-inflammatory mediators. It also has antioxidant activity by scavenging free radicals. Chelidonic acid may also modulate calcium signaling pathways in cells.
ln Vitro
Chelidonic acid suppresses IL-6 mRNA expression at 1–10 μM and dose-dependently lowers IL-6 production at 0.1–10 μM [1]. Chelidonic acid (0.1–10 μM) increases cytoplasmic NF-κB activation and decreases caspase-1 and nuclear NF-κB activation [1]. Chelidonic acid has a Ki of 1.2 μM, making it an inhibitor of glutamate decarboxylase. Chelidonic acid does not react with free pyridoxal-P or encourage the synthesis of apoenzymes [2].
Chelidonic acid demonstrates anti-inflammatory activity by inhibiting the production of pro-inflammatory cytokines and mediators. It has analgesic effects in animal models of pain. The compound exhibits antimicrobial activity against various bacteria and fungi. Chelidonic acid also shows hepatoprotective effects by reducing oxidative stress and liver enzyme levels. The compound has been shown to inhibit the activity of phospholipase A2 and other enzymes.
ln Vivo
Chelidonic acid (0.2, 2 mg/kg, orally) can lessen ovalbumin-induced allergy responses in mice [3].
Chelidonic acid has been studied in various in vivo models. In rodents, administration of chelidonic acid has been shown to reduce inflammation, pain, and liver injury. The compound has also been shown to have antimicrobial effects in animal models of infection. Its effects are dose-dependent and mediated through its anti-inflammatory and antioxidant properties. Further research is needed to fully characterize its in vivo pharmacological profile.
Enzyme Assay
The in vitro assay for chelidonic acid typically involves measuring its enzyme inhibitory activity using standard biochemical assays. The compound is tested against enzymes such as phospholipase A2, kinases, or other targets. The IC50 value is determined from the dose-response curve. Antioxidant activity is assessed using DPPH, ABTS, or FRAP assays. Antimicrobial activity is assessed using standard broth dilution or disk diffusion methods.
Cell Assay
The in vitro cellular assay for chelidonic acid typically involves culturing cell lines such as macrophages, hepatocytes, or cancer cells and treating them with varying concentrations of the compound. Cellular responses such as inflammatory cytokine secretion, oxidative stress markers, cell viability, and apoptosis are measured. The compound's effects on signaling pathways are assessed using Western blotting or reporter gene assays.
Animal Protocol
In vivo animal studies for chelidonic acid typically involve the administration of the compound to rodents via oral gavage or intraperitoneal injection. Parameters such as inflammatory markers, pain responses, and liver function tests are assessed. The compound's effects on various disease models (e.g., inflammation, pain, or liver injury) are evaluated. The compound is generally well tolerated at moderate doses.
ADME/Pharmacokinetics
Chelidonic acid is a small molecule with a molecular weight of 184.10 g/mol and a molecular formula of C7H4O6. It is soluble in water and organic solvents. The compound is metabolized in the liver and excreted in urine. It has a short half-life and is rapidly cleared from the body. The compound is stable under normal storage conditions and should be stored in a cool, dry place.
Toxicity/Toxicokinetics
Chelidonic acid is a naturally occurring compound and is generally well tolerated at moderate doses. However, high doses may cause gastrointestinal irritation or other adverse effects. The compound is intended for research use only and should be handled with appropriate laboratory safety precautions. Standard safety assessments would be required before any clinical application.
References

[1]. Inhibitory effects of chelidonic acid on IL-6 production by blocking NF-κB and caspase-1 in HMC-1 cells. Immunopharmacol Immunotoxicol. 2011 Dec;33(4):614-9.

[2]. Chelidonic acid and other conformationally restricted substrate analogues as inhibitors of rat brain glutamate decarboxylase. Biochem Pharmacol. 1985 Dec 1;34(23):4145-50.

[3]. Beneficial effects of chelidonic acid on a model of allergic rhinitis. Send to Int Immunopharmacol. 2011 Jan;11(1):39-45.

Additional Infomation
Chelidonic acid is a carbonyl compound belonging to the pyran group. It has been reported that Chelidonic acid is found in corn, chelidinium, and other organisms with relevant data. See also: Chelidinium inflorescence (partial).
Chelidonic acid is a naturally occurring organic acid found in Chelidonium majus (greater celandine) and other plants. It is a γ-pyrone derivative that is structurally related to meconic acid. The compound has been studied for its anti-inflammatory, analgesic, antimicrobial, and hepatoprotective effects. It is primarily used in research as a natural product and biochemical tool. The compound has not yet entered clinical trials and is strictly for preclinical research purposes.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C7H4O6
Molecular Weight
184.1031
Exact Mass
184.001
CAS #
99-32-1
PubChem CID
7431
Appearance
Gray to brown solid powder
Density
1.821 g/cm3
Boiling Point
471.3ºC at 760 mmHg
Melting Point
265 °C (dec.)(lit.)
Flash Point
204.1ºC
LogP
0.036
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
2
Heavy Atom Count
13
Complexity
316
Defined Atom Stereocenter Count
0
InChi Key
PBAYDYUZOSNJGU-UHFFFAOYSA-N
InChi Code
InChI=1S/C7H4O6/c8-3-1-4(6(9)10)13-5(2-3)7(11)12/h1-2H,(H,9,10)(H,11,12)
Chemical Name
4-oxopyran-2,6-dicarboxylic 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 : ~10 mg/mL (~54.32 mM)
H2O : ~2.5 mg/mL (~13.58 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (13.58 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 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 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to 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.

Solubility in Formulation 2: ≥ 2.5 mg/mL (13.58 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in 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 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
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.

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Solubility in Formulation 3: 2 mg/mL (10.86 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication (<60°C).


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.4318 mL 27.1592 mL 54.3183 mL
5 mM 1.0864 mL 5.4318 mL 10.8637 mL
10 mM 0.5432 mL 2.7159 mL 5.4318 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:

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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?
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  • 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:
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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
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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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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