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| Other Sizes |
| Targets |
Methyl cinnamate targets multiple pathways including tyrosinase, CaMKK2-AMPK, and Ca2+ channels. It acts as a tyrosinase inhibitor, which is relevant for its antimicrobial and potential skin-lightening effects. The compound activates the CaMKK2-AMPK pathway, which is involved in metabolic regulation. It also modulates Ca2+ channels, contributing to its vasorelaxant effects. These diverse targets explain its wide range of biological activities.
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| ln Vitro |
Methyl Cinnamate (methyl 3-phenylacrylate) suppresses adipocyte differentiation in the 3T3-L1 cell model by reducing the expression of adipogenic transcription factors SREBP-1, PPARγ, and C/EBPα, as well as PPARγ's transcriptional activity. Furthermore, methyl cinnamate, also known as methyl 3-phenylacrylate, triggers the CaMKK2−AMPK signaling cascade that controls adipogenesis [1].
In vitro, Methyl cinnamate demonstrates antimicrobial activity against various pathogens including Candida glabrata. It functions as a tyrosinase inhibitor. The compound inhibits adipocyte differentiation via activation of the CaMKK2-AMPK pathway in 3T3-L1 cells. It exhibits vasorelaxant effects through modulation of Ca2+ channels. Methyl cinnamate also shows anti-inflammatory effects. Its antibacterial activity involves binding to DNA monomers and blocking polymerase chain reaction. |
| ln Vivo |
In vivo, Methyl cinnamate has been studied for its various pharmacological effects. Its antiadipogenic effects suggest potential applications in obesity and metabolic disorders. The compound's vasorelaxant properties may have cardiovascular implications. As a flavoring agent, it is widely used in food products. In vivo studies have investigated its antimicrobial and anti-inflammatory effects. The compound's safety as a food additive has been established through regulatory evaluations.
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| Enzyme Assay |
The cell-free assay for Methyl cinnamate involves measuring its inhibitory activity against tyrosinase. Tyrosinase activity is monitored spectrophotometrically by measuring the oxidation of L-DOPA to dopachrome at 475 nm. Inhibition is assessed by incubating tyrosinase with varying concentrations of Methyl cinnamate and measuring residual activity. IC50 values are determined from dose-response curves. The compound's binding to DNA monomers can also be studied using biophysical techniques.
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| Cell Assay |
For in vitro cellular assays, Methyl cinnamate is typically dissolved in DMSO and diluted in cell culture medium. 3T3-L1 preadipocytes are treated with various concentrations of the compound during differentiation. Adipocyte differentiation is assessed by Oil Red O staining and measurement of adipogenic markers. Antimicrobial activity is evaluated using broth microdilution methods to determine MIC values. Anti-inflammatory effects are assessed by measuring cytokine production in activated immune cells.
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| Animal Protocol |
In vivo animal studies for Methyl cinnamate are typically conducted in mouse models of metabolic or inflammatory diseases. The compound can be administered via oral gavage or dietary inclusion. Body weight, food intake, and metabolic parameters are monitored. Adipose tissue weight and histology are assessed. Inflammatory markers in serum and tissues are measured using ELISA. Safety and tolerability are evaluated through standard toxicology assessments.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of Methyl cinnamate include a molecular weight of 162.19 g/mol and molecular formula C10H10O2. As a flavoring compound, it is well-absorbed and metabolized. The compound is naturally found in various plants and is generally recognized as safe for food use. It is typically handled as a liquid or solid and stored at appropriate conditions. Detailed ADME parameters are available from food safety and toxicology studies.
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| Toxicity/Toxicokinetics |
The toxicity profile of Methyl cinnamate has been well-characterized due to its widespread use as a flavoring agent. It is generally recognized as safe (GRAS) for food use. Standard toxicology studies include acute, sub-chronic, and chronic toxicity assessments. The compound is not classified as a carcinogen or mutagen. Allergic reactions are possible in sensitive individuals. The compound is intended for research and food use, not for therapeutic applications.
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| References | |
| Additional Infomation |
Methyl cinnamate is a product of the condensation of methyl cinnamate and methanol. It is naturally found in ginger family plants (such as galangal) and basil leaf oil, and is widely used in the fragrance and flavor industry. Methyl cinnamate has various uses, including as a flavoring agent, spice, insect attractant, volatile oil component, and anti-inflammatory agent. It is a methyl ester and also an alkyl cinnamate ester. Methyl cinnamate has been reported to be present in Hainan ginger (Alpinia hainanensis), thornless ginger (Alpinia mutica), and several other organisms with relevant data. Methyl cinnamate is also a metabolite of or produced by the yeast Saccharomyces cerevisiae.
Methyl cinnamate is an active component of Zanthoxylum armatum and a widely used natural flavor compound with antimicrobial, antiadipogenic, vasorelaxant, and anti-inflammatory effects. It inhibits tyrosinase and activates the CaMKK2-AMPK pathway. The compound inhibits adipocyte differentiation in 3T3-L1 cells and shows antimicrobial activity against various pathogens. Methyl cinnamate is generally recognized as safe for food use and is widely used in the fragrance and food industries. It is strictly for research and food applications, not for therapeutic use. |
| Molecular Formula |
C10H10O2
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|---|---|
| Molecular Weight |
162.1852
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| Exact Mass |
162.068
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| CAS # |
103-26-4
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| PubChem CID |
637520
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| Appearance |
White to off-white <34°C powder,>38°C liquid
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
261.9±0.0 °C at 760 mmHg
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| Melting Point |
34-38 °C(lit.)
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| Flash Point |
141.3±9.9 °C
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| Vapour Pressure |
0.0±0.5 mmHg at 25°C
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| Index of Refraction |
1.559
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| Source |
Originated from plants: Rutaceae Zanthoxylum armatum DC.
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| LogP |
2.18
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
12
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| Complexity |
167
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O(C)C(/C=C/C1C=CC=CC=1)=O
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| InChi Key |
CCRCUPLGCSFEDV-BQYQJAHWSA-N
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| InChi Code |
InChI=1S/C10H10O2/c1-12-10(11)8-7-9-5-3-2-4-6-9/h2-8H,1H3/b8-7+
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| Chemical Name |
methyl (E)-3-phenylprop-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 (~616.56 mM)
H2O : ~1 mg/mL (~6.17 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (15.41 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 (15.41 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 (15.41 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 2 mg/mL (12.33 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication (<60°C). |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.1656 mL | 30.8280 mL | 61.6561 mL | |
| 5 mM | 1.2331 mL | 6.1656 mL | 12.3312 mL | |
| 10 mM | 0.6166 mL | 3.0828 mL | 6.1656 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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