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| Targets |
Methyl p-coumarate targets multiple biological processes. It is an inhibitor of melanin synthesis, as demonstrated by its ability to inhibit melanin formation in B16 mouse melanoma cells. It also exhibits antifungal activity, with strong in vitro inhibitory effects against Alternaria and other pathogens. Additionally, it has antibacterial properties and acts as an anti-inflammatory agent. These diverse activities make it a candidate for research in microbiology, dermatology, and inflammation.
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| ln Vitro |
In vitro, Methyl p-coumarate demonstrates significant biological activity. It inhibits melanin formation in B16 mouse melanoma cells, making it a valuable tool for studying skin pigmentation disorders. It also has strong in vitro inhibitory effects against Alternaria and other pathogens. These activities are typically assessed in cell-based assays measuring melanin content or fungal growth inhibition. The compound's antibacterial and antifungal properties are confirmed in standard antimicrobial susceptibility tests.
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| ln Vivo |
In vivo studies for Methyl p-coumarate are not extensively detailed in the provided literature. As a naturally occurring compound with antibacterial and anti-melanogenesis properties, it has potential for in vivo applications in dermatology and infectious disease research. Studies in appropriate animal models would be needed to evaluate its in vivo efficacy, pharmacokinetics, and safety profile. Its role as a plant metabolite suggests it may be well-tolerated.
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| Enzyme Assay |
For non-cellular enzyme/receptor binding studies, Methyl p-coumarate's activity could be evaluated in biochemical assays targeting melanin synthesis enzymes, such as tyrosinase. Its antifungal activity can be assessed using standard antimicrobial susceptibility testing methods, where the compound is tested against fungal cultures to determine its minimum inhibitory concentration (MIC). These assays provide insights into its mechanism of action as a melanin synthesis inhibitor and antifungal agent.
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| Cell Assay |
For in vitro cellular experiments, B16 mouse melanoma cells are cultured and treated with Methyl p-coumarate at various concentrations to assess its effect on melanin formation. Melanin content is measured spectrophotometrically. For antifungal studies, fungal cultures such as Alternaria are grown and treated with the compound, and growth inhibition is measured. Cell viability is assessed using standard assays to ensure that the observed effects are not due to cytotoxicity.
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| Animal Protocol |
In vivo animal studies for Methyl p-coumarate are not extensively documented. However, its potential for in vivo applications in dermatology and infectious disease research is suggested by its in vitro activities. Studies in animal models of skin pigmentation disorders or fungal infections would be needed to evaluate its in vivo efficacy. The compound could be administered topically or orally, and its effects would be assessed by measuring melanin content or pathogen load.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of Methyl p-coumarate are not extensively detailed in the provided sources. It has a molecular weight of 178.18 and is an off-white to light yellow solid powder. It is soluble in DMSO at 100 mg/mL (561.23 mM). For long-term storage, the powder should be kept at -20°C for 3 years or 4°C for 2 years. In solvent, it is stable for 6 months at -80°C or 1 month at -20°C. It is stable at ambient temperature for short periods.
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| Toxicity/Toxicokinetics |
The toxicity profile of Methyl p-coumarate is not explicitly detailed in the provided sources. As a naturally occurring compound with roles as a plant metabolite, it is likely to have a favorable safety profile. However, standard laboratory safety precautions should be followed when handling it. It is intended for research use only and is not for human therapeutic applications. Comprehensive toxicological studies are needed to fully evaluate its safety.
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| References |
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| Additional Infomation |
Methyl 4-coumarate is a cinnamic ester, a methyl ester derivative of 4-coumaric acid. It possesses multiple functions, including inhibiting melanin synthesis, acting as a fungal metabolite, an anti-inflammatory agent, an antifungal agent, and a plant metabolite. It is a cinnamic ester, belonging to the phenolic class of compounds, and is also a methyl ester. Its functions are related to 4-coumaric acid. Methyl 4-hydroxycinnamic acid has been reported in Alpinia blepharocalyx, Gmelina asiatica, and several other organisms with relevant data.
Methyl p-coumarate is an esterified analogue of p-coumaric acid with a molecular formula of C10H10O3 and a molecular weight of 178.18. It is extracted from Trixis michuacana var longifolia and exhibits antibacterial, antifungal, and anti-melanogenesis properties. It inhibits melanin formation in B16 cells and has strong in vitro inhibitory effects against Alternaria. This research compound is for laboratory use only and has not been approved for clinical applications. |
| Molecular Formula |
C10H10O3
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| Molecular Weight |
178.18
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| Exact Mass |
178.062
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| CAS # |
3943-97-3
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| Related CAS # |
(E)-Methyl 4-coumarate;19367-38-5
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| PubChem CID |
5319562
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| Appearance |
Off-white to light yellow solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
306.6±17.0 °C at 760 mmHg
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| Melting Point |
144-145ºC
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| Flash Point |
132.8±13.7 °C
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| Vapour Pressure |
0.0±0.7 mmHg at 25°C
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| Index of Refraction |
1.593
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| LogP |
1.64
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
13
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| Complexity |
190
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| Defined Atom Stereocenter Count |
0
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| SMILES |
COC(=O)/C=C/C1=CC=C(C=C1)O
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| InChi Key |
NITWSHWHQAQBAW-QPJJXVBHSA-N
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| InChi Code |
InChI=1S/C10H10O3/c1-13-10(12)7-4-8-2-5-9(11)6-3-8/h2-7,11H,1H3/b7-4+
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| Chemical Name |
methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
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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 (561.23 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (14.03 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
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 (14.03 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (14.03 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 | 5.6123 mL | 28.0615 mL | 56.1230 mL | |
| 5 mM | 1.1225 mL | 5.6123 mL | 11.2246 mL | |
| 10 mM | 0.5612 mL | 2.8062 mL | 5.6123 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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