| Size | Price | Stock | Qty |
|---|---|---|---|
| 10g |
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| 25g |
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| Other Sizes |
| Targets |
Coumalic acid functions as an inhibitor of human carbonic anhydrase (hCA), with a KI of 0.073 μM for hCA IX and 0.083 μM for hCA XII. Carbonic anhydrases are zinc-containing enzymes that catalyze the reversible hydration of carbon dioxide to bicarbonate and protons. They are involved in various physiological processes, including pH regulation, fluid secretion, and CO2 transport. Inhibition of carbonic anhydrase is being investigated for the treatment of various diseases, including cancer, glaucoma, and epilepsy. The compound's higher affinity for hCA IX and XII, which are tumor-associated carbonic anhydrases, suggests potential as an anticancer agent. The compound also displays antibronchial and antimalarial activity, suggesting that it may target pathways involved in bronchial inflammation and malaria parasite survival.
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| ln Vitro |
In vitro, coumalic acid is an inhibitor of human carbonic anhydrase, with a KI of 0.073 μM for hCA IX and 0.083 μM for hCA XII. It displays antibronchial and antimalarial activity. The compound is a valuable platform compound that can be prepared from malic acid. It may be used in the flavoring, fragrance, and cosmetic industries as a polymer component and as an active molecular scaffold. In medicinal chemistry, it serves as a building block for constructing biologically active molecules. Its coumarin-like structure provides a scaffold for the synthesis of various derivatives with potential biological activity.
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| ln Vivo |
In vivo, coumalic acid displays antibronchial and antimalarial activity. This suggests that the compound or its derivatives may have therapeutic potential for the treatment of bronchial conditions and malaria. However, specific in vivo studies on the compound are limited. The compound's carbonic anhydrase inhibitory activity suggests potential for in vivo evaluation in cancer models, but comprehensive studies have not been performed.
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| Enzyme Assay |
Cell-free assays for coumalic acid involve studying its carbonic anhydrase inhibitory activity. The compound is incubated with human carbonic anhydrase enzymes (hCA IX and hCA XII) and a suitable substrate, and enzymatic activity is measured spectrophotometrically or fluorometrically. The compound's KI values of 0.073 μM for hCA IX and 0.083 μM for hCA XII are determined. The compound's antibronchial and antimalarial activities can be assessed using relevant biochemical assays. Its antioxidant activity can be assessed using standard antioxidant assays such as DPPH or ABTS.
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| Cell Assay |
Cellular assays for coumalic acid involve testing its activity in cell-based systems. For carbonic anhydrase inhibition, cancer cell lines expressing hCA IX or XII are treated with the compound, and cell viability, proliferation, and pH regulation are assessed. For antimalarial activity, Plasmodium cultures are treated with the compound, and parasite growth inhibition is measured. For antibronchial activity, bronchial epithelial cells or smooth muscle cells are treated with the compound, and inflammatory markers or contractility are assessed. The compound's antioxidant activity can be assessed in cell-based oxidative stress models.
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| Animal Protocol |
Animal studies for coumalic acid are limited. The compound's antibronchial and antimalarial activities suggest potential for in vivo evaluation in animal models of bronchial inflammation and malaria. Its carbonic anhydrase inhibitory activity suggests potential for in vivo evaluation in cancer models. However, specific in vivo studies on the compound are not extensively documented.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for coumalic acid are not well characterized. As a small polar molecule with a molecular weight of 140.09 g/mol, it is expected to have moderate bioavailability if administered. However, comprehensive pharmacokinetic studies, including absorption, distribution, metabolism, and excretion, have not been performed. For research purposes, the compound is typically handled as a neat chemical and not administered to living organisms for pharmacokinetic profiling.
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| Toxicity/Toxicokinetics |
Toxicological data for coumalic acid are limited. Standard safety precautions for handling carboxylic acids and coumarin derivatives apply, including the use of personal protective equipment such as gloves and safety goggles. The compound should be handled in a well-ventilated area, and contact with skin and eyes should be avoided. In case of exposure, affected areas should be rinsed thoroughly with water. The compound is not classified as a carcinogen or mutagen based on available data, but comprehensive toxicological evaluation has not been performed. As with all research chemicals, it should be handled with care and used only in accordance with safety guidelines.
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| References | |
| Additional Infomation |
Coumalic acid is a pyranone.
Coumalic acid is a research chemical, not an approved drug. It has no clinical trial or marketing approval status for therapeutic use. The compound is an inhibitor of human carbonic anhydrase, with a KI of 0.073 μM for hCA IX and 0.083 μM for hCA XII. It displays antibronchial and antimalarial activity. The compound may be used in the flavoring, fragrance, and cosmetic industries as a polymer component and as an active molecular scaffold. It is a valuable platform compound that can be prepared from malic acid. It is supplied with a purity of ≥97.65% and should be stored in a cool, dry place. p-Coumaric acid, a related compound, has been shown to possess strong antioxidant activity. |
| Molecular Formula |
C6H4O4
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|---|---|
| Molecular Weight |
140.09
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| Exact Mass |
140.01
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| CAS # |
500-05-0
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| PubChem CID |
68141
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| Appearance |
Light yellow to brown solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
282.4±0.0 °C at 760 mmHg
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| Melting Point |
203-205 °C (dec.)(lit.)
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| Flash Point |
137.3±19.4 °C
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| Vapour Pressure |
0.0±1.2 mmHg at 25°C
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| Index of Refraction |
1.577
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| LogP |
-0.43
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
10
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| Complexity |
236
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=CC(=O)OC=C1C(=O)O
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| InChi Key |
ORGPJDKNYMVLFL-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C6H4O4/c7-5-2-1-4(3-10-5)6(8)9/h1-3H,(H,8,9)
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| Chemical Name |
6-oxopyran-3-carboxylic acid
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
DMSO: 250 mg/mL (1784.57 mM)
H2O: 2 mg/mL (14.28 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (14.85 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 20.8 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 7.1383 mL | 35.6913 mL | 71.3827 mL | |
| 5 mM | 1.4277 mL | 7.1383 mL | 14.2765 mL | |
| 10 mM | 0.7138 mL | 3.5691 mL | 7.1383 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.
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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