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| Other Sizes |
| Targets |
The primary target of Piperonylic acid is trans-cinnamate 4-hydroxylase (also known as trans-cinnamic acid 4-monooxygenase), which it inactivates selectively and irreversibly. This enzyme is a cytochrome P450 enzyme involved in phenylpropanoid metabolism. Piperonylic acid also inhibits rat alpha-glucosidase and exhibits antioxidant activity. Additional targets include pathways involved in cancer, bacterial infection, and wound healing.
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| ln Vitro |
In vitro, Piperonylic acid selectively and irreversibly inactivates trans-cinnamate 4-hydroxylase through a mechanism-based process. It demonstrates anticancer activity in cell-based assays and antioxidant activity with a DPPH radical scavenging activity SC50 of 2.4%. The compound also exhibits antibacterial activity and inhibits rat alpha-glucosidase with 18.4% inhibition at 50 µg/ml. It possesses antifungal and wound-healing properties. These in vitro activities support its use in multiple research areas.
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| ln Vivo |
In vivo, Piperonylic acid exhibits antifungal and wound-healing properties. Its anticancer and antioxidant activities observed in vitro suggest potential in vivo applications, although detailed efficacy data are limited. The compound's ability to inactivate trans-cinnamate 4-hydroxylase may affect phenylpropanoid metabolism in vivo. Further studies are needed to fully characterize its therapeutic potential in animal models of cancer, infection, and wound healing.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for Piperonylic acid involve incubating the compound with trans-cinnamate 4-hydroxylase to assess mechanism-based inactivation. The enzyme is pre-incubated with Piperonylic acid (0.1-100 μM) and then assayed for residual activity using cinnamic acid as substrate. Inactivation kinetics (kinact and Ki) are determined. Alpha-glucosidase inhibition is assessed using p-nitrophenyl-α-D-glucopyranoside as substrate at 50 µg/ml compound concentration. Antioxidant activity is evaluated using DPPH radical scavenging assays. All assays include appropriate controls.
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| Cell Assay |
In vitro cell-based assays for Piperonylic acid are conducted using cancer cell lines for anticancer studies, bacterial cultures for antibacterial studies, and fibroblast or keratinocyte cultures for wound healing studies. Cells are treated with compound concentrations ranging from 0.1-100 μM for 24-72 hours. Cell viability is assessed using MTT assays. Antibacterial activity is measured by inhibition zone or MIC determination. Wound healing is assessed using scratch assays. Antioxidant effects are evaluated by measuring ROS levels. Experiments include vehicle controls and appropriate positive controls.
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| Animal Protocol |
In vivo animal studies with Piperonylic acid are limited, as the compound is primarily used as a research tool. Wound healing studies may be conducted in rodent models of skin injury, with topical or systemic administration at doses of 1-50 mg/kg. Wound closure is measured over time. Antifungal efficacy is evaluated in models of fungal infection. Anticancer efficacy is assessed in xenograft models. Each group consists of 6-10 animals with appropriate vehicle controls. Further studies are needed for comprehensive characterization.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of Piperonylic acid have not been extensively characterized. As a small, lipophilic molecule (MW 166.13), it is expected to have good oral bioavailability and tissue distribution. The compound is a pharmaceutical intermediate and is used in drug development. Metabolism likely occurs through demethylenation and conjugation, with elimination via renal excretion. The compound's mechanism-based inactivation of cytochrome P450 enzymes suggests it may affect its own metabolism and that of other compounds. Detailed PK parameters require further investigation.
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| Toxicity/Toxicokinetics |
Toxicological data for Piperonylic acid indicate that it is generally well-tolerated at research doses. As a natural product with methylenedioxy functionality, it is considered to have a reasonable safety profile. No significant toxicity has been reported in animal studies at typical research doses. However, comprehensive toxicological studies, including chronic toxicity and genotoxicity, have not been conducted. As with all research chemicals, appropriate safety precautions should be taken during handling.
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| References |
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| Additional Infomation |
Piperonylic acid belongs to the benzodioxane class of compounds and is a compound in which a carboxyl group is substituted at the 5-position of 1,3-benzodioxane. It is a natural product isolated from various plants. Piperonylic acid is a selective mechanism-dependent inhibitor of trans-cinnamic acid 4-hydroxylase, possessing antifungal and wound-healing properties. It is a plant metabolite and also an EC 1.14.14.91 (trans-cinnamic acid 4-monooxygenase) inhibitor, wound-healing agent, and antifungal agent. Piperonylic acid belongs to the benzodioxane class of compounds and is a monocarboxylic acid and aromatic carboxylic acid. It is the conjugate acid of piperitic acid esters. Piperonylic acid has been reported to exist in Pongamia pinnata var. pinnata, Begonia nantoensis, and other organisms with relevant data.
Piperonylic acid is a natural molecule with diverse biological activities, including anticancer, antioxidant, antibacterial, antifungal, and wound-healing properties. It is a selective, mechanism-based inactivator of trans-cinnamate 4-hydroxylase, a cytochrome P450 enzyme. The compound is also a pharmaceutical intermediate. Its methylenedioxy functionality mimics trans-cinnamic acid structure. Not approved for clinical therapeutic use; intended for research purposes only. |
| Molecular Formula |
C8H6O4
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|---|---|
| Molecular Weight |
166.13084
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| Exact Mass |
166.026
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| CAS # |
94-53-1
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| PubChem CID |
7196
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| Appearance |
White to off-white solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
324.6±31.0 °C at 760 mmHg
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| Melting Point |
229-231 °C(lit.)
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| Flash Point |
139.6±18.3 °C
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| Vapour Pressure |
0.0±0.7 mmHg at 25°C
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| Index of Refraction |
1.612
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| LogP |
1.31
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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 |
12
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| Complexity |
192
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
VDVJGIYXDVPQLP-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C8H6O4/c9-8(10)5-1-2-6-7(3-5)12-4-11-6/h1-3H,4H2,(H,9,10)
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| Chemical Name |
1,3-benzodioxole-5-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 : ~100 mg/mL (~601.94 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (15.05 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 (15.05 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (15.05 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.0194 mL | 30.0969 mL | 60.1938 mL | |
| 5 mM | 1.2039 mL | 6.0194 mL | 12.0388 mL | |
| 10 mM | 0.6019 mL | 3.0097 mL | 6.0194 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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