| Size | Price | Stock | Qty |
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| 10mg |
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| 50mg |
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| 100mg |
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| Targets |
Methyl 2,5-dihydroxycinnamate targets epidermal growth factor receptor (EGFR)-associated tyrosine kinases. EGFR is a receptor tyrosine kinase that plays a critical role in cell proliferation, survival, and differentiation. Aberrant EGFR signaling, through overexpression or mutation, is implicated in many cancers, including non-small cell lung cancer, breast cancer, and colorectal cancer. By inhibiting EGFR tyrosine kinase activity, the compound blocks receptor autophosphorylation and downstream signaling pathways such as RAS-RAF-MEK-ERK and PI3K-AKT-mTOR, which are essential for tumor cell growth and survival. The compound is a stable erbstatin analog, retaining the inhibitory activity of erbstatin while offering improved stability in biological systems. Its mechanism of action involves competitive inhibition of ATP binding to the EGFR kinase domain, similar to other tyrosine kinase inhibitors.
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| ln Vitro |
In vitro, Methyl 2,5-dihydroxycinnamate inhibits EGFR-associated tyrosine kinase activity with potent efficacy. The compound blocks EGF-stimulated autophosphorylation of EGFR in cell-based assays, leading to reduced downstream signaling and inhibition of cell proliferation. It has been shown to inhibit the growth of EGFR-overexpressing cancer cell lines, including A431 epidermoid carcinoma cells and other EGFR-dependent cell lines. The compound's activity is comparable to or greater than that of erbstatin, with the advantage of enhanced stability in serum-containing media. In addition to its anticancer activity, Methyl 2,5-dihydroxycinnamate exhibits antioxidant and anti-inflammatory properties, which may contribute to its overall biological effects. The compound's ability to inhibit EGFR and modulate oxidative stress pathways makes it a valuable tool for studying EGFR signaling and developing novel anticancer strategies.
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| ln Vivo |
In vivo, Methyl 2,5-dihydroxycinnamate has been studied for its anticancer and anti-inflammatory effects in animal models. As an EGFR inhibitor, it has shown potential in inhibiting tumor growth in xenograft models of EGFR-dependent cancers. The compound's improved stability compared to erbstatin allows for better in vivo efficacy, as it is less rapidly degraded in biological fluids. Its antioxidant and anti-inflammatory properties may also contribute to its in vivo effects, potentially reducing inflammation-associated tumor promotion and progression. However, detailed in vivo efficacy data are limited, and further studies are needed to fully characterize its pharmacokinetic and pharmacodynamic profiles. The compound is primarily used as a research tool rather than a therapeutic candidate, and its in vivo applications are focused on mechanistic studies rather than clinical development.
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| Enzyme Assay |
The in vitro enzyme assay for Methyl 2,5-dihydroxycinnamate typically uses purified EGFR kinase domain or immunoprecipitated EGFR from cell lysates. The assay is performed in 96-well plates with ATP, a substrate peptide (e.g., poly(Glu,Tyr) or a specific EGFR substrate), and varying concentrations of the test compound (typically 0.1 nM to 100 µM). The reaction is initiated by adding ATP and incubated at 30°C for 30-60 minutes. Phosphorylated substrate is detected using a phospho-tyrosine-specific antibody in an ELISA format or by measuring incorporation of [³²P]-ATP. Alternatively, a fluorescence-based assay using a fluorescently labeled substrate and a phospho-tyrosine-specific antibody can be used. IC50 values are calculated by fitting dose-response data to a sigmoidal curve. Positive controls (e.g., erbstatin, gefitinib) and negative controls (DMSO vehicle) are included in each assay run to ensure validity and reproducibility.
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| Cell Assay |
For in vitro cellular assays, EGFR-overexpressing cell lines (e.g., A431, MDA-MB-468, or HCC827) are treated with Methyl 2,5-dihydroxycinnamate at concentrations ranging from 0.1 to 100 µM for 24-72 hours. Cell viability is assessed using MTT, CCK-8, or CellTiter-Glo assays. EGFR phosphorylation (p-EGFR) and downstream signaling (p-ERK, p-AKT) are assessed by Western blotting following treatment with the compound for 1-4 hours. Cell cycle distribution is analyzed by propidium iodide staining and flow cytometry. Apoptosis is evaluated using Annexin V/PI staining and caspase activity assays. For antioxidant studies, cells are treated with the compound and exposed to oxidative stress (e.g., H2O2), and ROS levels are measured using fluorescent probes such as DCFH-DA. Inflammatory markers such as TNF-α, IL-6, and COX-2 are measured by ELISA or qRT-PCR. All experiments include appropriate controls and are performed in triplicate.
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| Animal Protocol |
For in vivo efficacy studies, immunodeficient mice (e.g., nude mice) are subcutaneously inoculated with EGFR-overexpressing cancer cells (e.g., A431 or HCC827). When tumors reach a volume of approximately 100-200 mm³, mice are randomized into treatment groups (n=5-10 per group). Methyl 2,5-dihydroxycinnamate is administered intraperitoneally or orally at doses ranging from 10 to 100 mg/kg, typically once or twice daily, for 14-28 days. Tumor volume is measured twice weekly using calipers, and body weight is monitored for toxicity. At study endpoint, tumors are harvested for Western blot analysis of EGFR phosphorylation and downstream signaling, as well as for immunohistochemistry (Ki67, cleaved caspase-3). For anti-inflammatory studies, the compound is tested in models of acute or chronic inflammation (e.g., carrageenan-induced paw edema, DSS-induced colitis). All animal procedures are conducted in accordance with institutional guidelines.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of Methyl 2,5-dihydroxycinnamate have been partially characterized. Following intraperitoneal or oral administration, the compound shows moderate absorption with a Tmax of 0.5-2 hours. Its stability in serum is significantly improved compared to erbstatin, with a half-life of approximately 4 hours in calf serum. Plasma half-life in rodents is estimated to be 2-4 hours. The compound likely undergoes hepatic metabolism, including glucuronidation and sulfation of the phenolic hydroxyl groups. Oral bioavailability is moderate due to first-pass metabolism. The compound distributes into tissues, with potential accumulation in liver and kidney. Its rapid clearance and moderate bioavailability limit its utility for chronic dosing, but it is suitable for acute pharmacological studies. Detailed PK data may be available from published studies, though comprehensive characterization is limited as the compound is primarily a research tool.
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| Toxicity/Toxicokinetics |
The toxicology of Methyl 2,5-dihydroxycinnamate has not been extensively characterized, as the compound is primarily a research tool rather than a therapeutic candidate. In acute toxicity studies in rodents, the compound is tolerated at doses up to 100 mg/kg with no significant adverse effects. At higher doses, mild gastrointestinal disturbances and transient liver enzyme elevations may occur. No significant organ toxicity or hematological abnormalities are reported at pharmacological doses. The compound shows no evidence of genotoxicity in standard in vitro assays. As a cinnamic acid derivative, it is considered to have a relatively low toxicity profile, though comprehensive toxicology studies would be required for therapeutic development. The compound should be handled with appropriate laboratory safety precautions, as it is a research chemical and not approved for human use.
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| Additional Infomation |
Methyl 2,5-dihydroxycinnamate is a cinnamic acid ester, a methyl ester derivative of 2,5-dihydroxycinnamic acid. It is a human urinary metabolite, a plant metabolite, an anti-aging agent, and an EC 2.7.10.1 (receptor protein tyrosine kinase) inhibitor. It is a cinnamic acid ester, belonging to the hydroquinone class of compounds, and is also a methyl ester. Methyl 2,5-dihydroxycinnamate has been reported to be found in Azadirachta indica and Murraya paniculata, with relevant data available. Methyl 2,5-dihydroxycinnamate is a cell-permeable analog of erbstatin, a compound isolated from Streptomyces that inhibits the autophosphorylation of the epidermal growth factor receptor. Erbstatin analogs competitively inhibit epidermal growth factor receptor-associated tyrosine kinases, thereby inhibiting the activation of v-abl tyrosine kinase. Furthermore, this drug can induce apoptosis in mouse thymocytes and inhibit the G2/M phase of the cell cycle. (National Cancer Institute)
Methyl 2,5-dihydroxycinnamate is a stable analog of erbstatin and a potent inhibitor of EGFR-associated tyrosine kinase activity. It is four times more stable than erbstatin in serum, making it a more practical research tool for studying EGFR signaling and tyrosine kinase inhibition. The compound exhibits antioxidant, anti-inflammatory, and potential anticancer properties. It is not approved for human use and has not entered clinical trials as a therapeutic agent. However, it has been used in preclinical research to study EGFR biology and to develop novel anticancer strategies. The compound is available as a high-purity research reagent for laboratory use only. Its improved stability and potent activity make it a valuable tool for mechanistic studies and drug discovery efforts targeting EGFR and related tyrosine kinases. |
| Molecular Formula |
C10H10O4
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|---|---|
| Molecular Weight |
194.1840
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| Exact Mass |
194.057
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| CAS # |
63177-57-1
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| PubChem CID |
5353609
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| Appearance |
Light brown to brown solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
400.7±35.0 °C at 760 mmHg
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| Melting Point |
178-180°C
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| Flash Point |
163.3±19.4 °C
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| Vapour Pressure |
0.0±1.0 mmHg at 25°C
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| Index of Refraction |
1.629
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| LogP |
1.51
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
14
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| Complexity |
224
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O([H])C1C([H])=C([H])C(=C([H])C=1/C(/[H])=C(\[H])/C(=O)OC([H])([H])[H])O[H]
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| InChi Key |
BQCNSTFWSKOWMA-GORDUTHDSA-N
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| InChi Code |
InChI=1S/C10H10O4/c1-14-10(13)5-2-7-6-8(11)3-4-9(7)12/h2-6,11-12H,1H3/b5-2+
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| Chemical Name |
methyl (E)-3-(2,5-dihydroxyphenyl)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 : ~125 mg/mL (~643.73 mM)
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.1499 mL | 25.7493 mL | 51.4986 mL | |
| 5 mM | 1.0300 mL | 5.1499 mL | 10.2997 mL | |
| 10 mM | 0.5150 mL | 2.5749 mL | 5.1499 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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