| Size | Price | Stock | Qty |
|---|---|---|---|
| 50g |
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| Other Sizes |
| Targets |
3,4-Methylenedioxycinnamic acid targets 4-hydroxycinnamoyl-CoA ligase, a key enzyme in the phenylpropanoid pathway. This enzyme is responsible for the activation of hydroxycinnamic acids by converting them to their corresponding CoA esters, which are then used in the biosynthesis of various plant secondary metabolites, including lignin, flavonoids, and other phenolic compounds. By inhibiting this enzyme, the compound disrupts the phenylpropanoid pathway, leading to an increase in the formation of soluble phenolics, especially vanillic acid. This mechanism makes it a valuable tool for studying phenylpropanoid metabolism in plants.
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| ln Vitro |
In vitro, 3,4-Methylenedioxycinnamic acid acts as an inhibitor of 4-hydroxycinnamoyl-CoA ligase. Its inhibitory activity has been demonstrated in enzyme assays measuring the conversion of hydroxycinnamic acids to their CoA esters. The compound promotes the accumulation of soluble phenolics, particularly vanillic acid, by blocking their further metabolism. This effect has been observed in plant cell cultures or in vitro enzyme systems. The compound has also been studied for its electron transfer reaction with trichloromethylperoxyl radical using pulse radiolysis, indicating its potential as an antioxidant or redox-active molecule.
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| ln Vivo |
In vivo activity of 3,4-Methylenedioxycinnamic acid has been studied in the context of plant physiology and allelopathy. As a plant-derived compound, it is characterized as an allelochemical, suggesting it may play a role in plant-plant interactions by inhibiting the growth of neighboring plants. Its effects on the phenylpropanoid pathway in plants can lead to changes in the accumulation of phenolic compounds, which may affect plant defense responses and development. However, specific in vivo pharmacological data in animal models are not detailed in the available literature.
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| Enzyme Assay |
In vitro enzyme assays for 3,4-Methylenedioxycinnamic acid typically involve measuring the inhibition of 4-hydroxycinnamoyl-CoA ligase activity. The enzyme is incubated with its substrate (e.g., 4-coumaric acid), coenzyme A, and ATP in a buffer solution. Varying concentrations of the compound are added to the reaction mixture, and the formation of the CoA ester is measured spectrophotometrically or by using a coupled enzyme assay. The IC50 value, representing the concentration required to inhibit 50% of the enzyme activity, is calculated from the dose-response curve. The compound is typically dissolved in DMSO or ethanol for stock solutions and diluted in the assay buffer.
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| Cell Assay |
In vitro cell-based assays using 3,4-Methylenedioxycinnamic acid are typically performed in plant cell cultures to study its effects on the phenylpropanoid pathway. Plant cells are treated with varying concentrations of the compound, and the accumulation of phenolic compounds, particularly vanillic acid, is measured using HPLC or other analytical techniques. The compound's effects on gene expression related to the phenylpropanoid pathway can also be studied using qPCR. The compound is typically dissolved in DMSO or ethanol and diluted in the plant culture medium.
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| Animal Protocol |
Specific in vivo animal experiment protocols for 3,4-Methylenedioxycinnamic acid are not detailed in the available literature. The compound is primarily studied in the context of plant biology and allelopathy. For potential studies in animal models, the compound could be formulated for administration, but its primary use is as a research tool for studying plant metabolism.
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| ADME/Pharmacokinetics |
3,4-Methylenedioxycinnamic acid has a molecular weight of 192.17 g/mol and the formula C10H8O4. It is an off-white to light yellow solid powder with a melting point of 242-244°C (dec.). The compound is soluble in DMSO at ≥ 100 mg/mL. For in vivo formulation, it can be prepared in a mixture of 10% DMSO, 40% PEG300, 5% Tween80, and 45% saline. For long-term storage, the powder is kept at -20°C for up to 3 years or at 4°C for up to 2 years. Its LogP is 2.53.
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| Toxicity/Toxicokinetics |
Specific toxicological data for 3,4-Methylenedioxycinnamic acid are not provided in the available sources. As a plant-derived compound, it is likely to have a relatively low toxicity profile. However, as a research chemical, it is intended for laboratory use only and is not for human consumption. Standard laboratory safety precautions should be followed when handling this compound, including the use of appropriate personal protective equipment. Its purity is typically ≥98%.
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| References | |
| Additional Infomation |
Methylenedioxycinnamic acid is a type of hydroxycinnamic acid. It has been reported to be found in both Brombya platynema and Helichrysum arenarium, and relevant data are available for reference.
3,4-Methylenedioxycinnamic acid is a plant-derived inhibitor of the phenylpropanoid enzyme 4-hydroxycinnamoyl-CoA ligase. It has the molecular formula C10H8O4 and a molecular weight of 192.17 g/mol. The compound promotes the formation of soluble phenolics, particularly vanillic acid. It was first isolated from asparagus roots and characterized as an allelochemical. The compound is also known as (E)-3-(1,3-benzodioxol-5-yl)prop-2-enoic acid. It appears as an off-white to light yellow solid powder and is soluble in DMSO. It is used in research to study plant metabolism and phenylpropanoid pathways and is intended for research use only. |
| Molecular Formula |
C10H8O4
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|---|---|
| Molecular Weight |
192.1681
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| Exact Mass |
192.042
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| CAS # |
2373-80-0
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| PubChem CID |
643181
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| Appearance |
Off-white to light yellow solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
361.5±11.0 °C at 760 mmHg
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| Melting Point |
242-244 °C (dec.)(lit.)
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| Flash Point |
148.9±12.8 °C
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| Vapour Pressure |
0.0±0.9 mmHg at 25°C
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| Index of Refraction |
1.653
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| LogP |
2.53
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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 |
2
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| Heavy Atom Count |
14
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| Complexity |
249
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1OC2=C(O1)C=C(C=C2)/C=C/C(=O)O
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| InChi Key |
QFQYZMGOKIROEC-DUXPYHPUSA-N
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| InChi Code |
InChI=1S/C10H8O4/c11-10(12)4-2-7-1-3-8-9(5-7)14-6-13-8/h1-5H,6H2,(H,11,12)/b4-2+
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| Chemical Name |
(E)-3-(1,3-benzodioxol-5-yl)prop-2-enoic 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 (~520.37 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 1 mg/mL (5.20 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 10.0 mg/mL clear DMSO stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of 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: ≥ 1 mg/mL (5.20 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 10.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.2037 mL | 26.0186 mL | 52.0373 mL | |
| 5 mM | 1.0407 mL | 5.2037 mL | 10.4075 mL | |
| 10 mM | 0.5204 mL | 2.6019 mL | 5.2037 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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