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4-Methoxycinnamic acid ethyl ester

Alias: Ethyl p-methoxycinnamate
4-Methoxycinnamate (ethyl p-methoxycinnamate) is an orally effective natural compound.
4-Methoxycinnamic acid ethyl ester
4-Methoxycinnamic acid ethyl ester Chemical Structure CAS No.: 1929-30-2
Product category: COX
This product is for research use only, not for human use. We do not sell to patients.
Size Price
500mg
1g
Other Sizes

Other Forms of 4-Methoxycinnamic acid ethyl ester:

  • (E)-Ethyl p-methoxycinnamate
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
4-Methoxycinnamic acid ethyl ester (Ethyl p-methoxycinnamate) is an orally effective natural compound. It exerts its anti-inflammatory effects by inhibiting cyclooxygenases (COX-1 (IC50 = 1.12 μM) and COX-2 (IC50 = 0.83 μM)), NF-κB (IC50 = 88.7 μM), and cytokine production (TNF-α (IC50 = 96.84 μg/mL) and IL-1β (IC50 = 166.4 μg/mL)). 4-Methoxycinnamic acid ethyl ester inhibits tumor cell proliferation, migration, and cancer metabolism, and induces apoptosis. It also inhibits VEGF expression, thereby suppressing angiogenesis. 4-Methoxycinnamic acid ethyl ester exhibits significant inhibitory effects against dengue virus and Mycobacterium tuberculosis. It also demonstrates analgesic effects in rats.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
4-Methoxycinnamic acid ethyl ester (25-200 μg/mL, 0-48 h) inhibited the growth of HUVECs with an IC50 of 160 μg/mL and inhibited the migration ability of HUVECs by VEGF [2]. 4-Methoxycinnamic acid ethyl ester (50-200 μg/mL, 6-24 h) dose-dependently impaired the ability of HUVECs to form tubular structures on Matrigel [2]. 4-Methoxycinnamic acid ethyl ester (50-200 μg/mL, 5 d) significantly inhibited the sprouting and growth of microvessels in the aortic ring of rats [2]. 4-Methoxycinnamic acid ethyl ester (0.03–0.97 mM, 7 d) inhibited Mycobacterium tuberculosis H37Ra, H37Rv, drug-sensitive and multidrug-resistant (MDR) clinical isolates (MIC: 0.242–0.485 mM), and was ineffective against common bacteria such as Mycobacterium smegmatis, Escherichia coli and Staphylococcus aureus [3]. 4-Methoxycinnamic acid ethyl ester (50 μM, 12 h) significantly reduced the phosphorylation levels of p-p65 (Ser536) and p-Akt (Ser473) in melanoma cells [4]. 4-Methoxycinnamic acid ethyl ester (50 μM, 24 h) significantly inhibited the migration and invasion of melanoma cells [4]. 4-Methoxycinnamic acid ethyl ester (1-50 μM, 12-24 h) reversed the resistance of melanoma cells to Paclitaxel[4]. 4-Methoxycinnamic acid ethyl ester (125-500 μM, 24 h) showed broad-spectrum antiviral activity against all four dengue serotypes (DENV-1, DENV-2, DENV-3, DENV-4), with EC50 values of 22.58 and 6.17 μM against DENV-2 in HepG2 and A549 cells, respectively[5]. 4-Methoxycinnamic acid ethyl ester (100 μM, 1-24 h) inhibited de novo fatty acid synthesis (rather than glycolysis) in Ehrlich ascites carcinoma cells (EATCs), thereby depleting ATP[6]. 4-Methoxycinnamic acid ethyl ester (48 h) showed moderate cytotoxicity against MCF-7, HT-29, HCT-116 (IC50 = 42.1 μg/mL), U-937, PC-3 (IC50 = 39 μg/mL), and K-562 cells [7]. 4-Methoxycinnamic acid ethyl ester (50–200 μg/mL, 12–48 h) inhibited the migration of HCT-116 cells and induced apoptosis via the mitochondrial pathway [7]. 4-Methoxycinnamic acid ethyl ester (200 μg/mL, 8 h) significantly activated all tested caspases, including caspase-9, caspase-8, and caspase-3/7, in HCT-116 cells [7].
ln Vivo
Ethyl 4-methoxycinnamate (100-800 mg/kg, single gavage) was administered in the field via monitoring to reduce paw edema[1]. Ethyl 4-methoxycinnamate (200-800 mg/kg, single gavage for 7 consecutive days) was administered in the field via reporting to reduce chronic granuloma formation[2]. (200-800 mg/kg, single gavage) was administered in a dose-dependent manner to prolong the latency period of tail hanging and showed significant analgesic effects[2].
Cell Assay
Cell Migration Assay [2]
Cell Types: HUVECs
Tested Concentrations: 50, 100, 200 μg/mL
Incubation Duration: 0, 6 and 12 h
Experimental Results: Effectively prevented the migration of endothelial cells to the damaged area.
Western Blot Analysis[4]
Cell Types: B16F10 G5-Luc and SK-Mel 28
Tested Concentrations: 50 μM
Incubation Duration: 12 h (B16F10 G5-Luc) and 24 h (SK-Mel 28)
Experimental Results: Significantly reduced the phosphorylation levels of p-p65 (Ser536) and p-Akt (Ser473). Upregulated the expression of γ-H2AX with Paclitaxel.
Cell Migration Assay [4]
Cell Types: B16F10 G5-Luc
Tested Concentrations: 50 μM
Incubation Duration: 12 h
Experimental Results: Significantly inhibited the migration.
Cell Invasion Assay[4]
Cell Types: B16F10 G5-Luc
Tested Concentrations: 50 μM
Incubation Duration: 12 h
Experimental Results: Significantly reduced the number of cells passing through Matrigel.
Western Blot Analysis[4]
Cell Types: 143B cells
Tested Concentrations: 2.5 μM
Incubation Duration: 1, 2, 4, 8, 16 and 24 h
Experimental Results: Activated caspases and increased PARP-1 cleavage. Promoted the phosphorylation of p53, and upregulated PUMA and Bax. Increased the level of γH2AX.
RT-PCR[6]
Cell Types: EATCs
Tested Concentrations: 100 μM
Incubation Duration: 1, 6 and 12 h
Experimental Results: Significantly downregulated the mRNA expression of key enzymes in fatty acid synthesis, including Acly, Acc1, and Fasn. Was no significant effect on the mRNA expression of key fatty acid oxidation enzymes Cpt1a and Cpt1b. Significantly downregulated the expression levels of SREBP1 mRNA.
Western Blot Analysis[6]
Cell Types: EATCs
Tested Concentrations: 100 μM
Incubation Duration: 1, 6 and 12 h
Experimental Results: Significantly reduced the phosphorylation level of c-Myc protein Ser62 site. Downregulated the expression of key enzymes in fatty acid synthesis (Acly, Acc1, Fasn).
Apoptosis Analysis[7]
Cell Types: HCT-116
Tested Concentrations: 50, 100, 200 μg/mL
Incubation Duration: 48 h
Experimental Results: Dose-dependently induced chromatin condensation in HCT-116 cells. Dose-dependent lost mitochondrial membrane potential.
Animal Protocol
Animal/Disease Models: Carrageenan-induced paw edema model established in male Sprague Dawely (SD) rats (150-200 g)[1]
Doses: 100, 200, 400 and 800 mg/kg
Route of Administration: Oral gavage (i.g.), single dose
Experimental Results: Inhibited paw edema in a dose-dependent manner, with the minimum effective dose (MIC) being 100 mg/kg. No toxic reactions were observed at 2000 mg/kg.
Animal/Disease Models: Cotton pellet granuloma assay established in male Sprague Dawely (SD) rats (200-250 g)[2]
Doses: 200, 400, 800 mg/kg
Route of Administration: Oral gavage (i.g.), once daily for 7 days
Experimental Results: Reached inhibition rate by 51.65% at 800 mg/kg. Inhibited the production of key pro-inflammatory cytokines IL-1β and TNF-α.
Animal/Disease Models: Tail flick assay established in male Sprague Dawely (SD) rats (200-250 g)[2]
Doses: 200, 400, 800 mg/kg
Route of Administration: Oral gavage (i.g.), single dose
Experimental Results: Prolonged the tail-flick latency of rats in a dose-dependent manner
References

[1]. Bioactivity-Guided Isolation of Ethyl-p-methoxycinnamate, an Anti-inflammatory Constituent, from Kaempferia galanga L. Extracts. Molecules. 2012 Jul 23;17(7):8720-34.

[2]. Ethyl-p-methoxycinnamate isolated from Kaempferia galanga inhibits inflammation by suppressing interleukin-1, tumor necrosis factor-α, and angiogenesis by blocking endothelial functions. Clinics (Sao Paulo). 2014 Feb;69(2):134-44.

[3]. Ethyl p-methoxycinnamate isolated from a traditional anti-tuberculosis medicinal herb inhibits drug resistant strains of Mycobacterium tuberculosis in vitro. Fitoterapia. 2011 Jun;82(4):757-61.

[4]. Ethyl P-Methoxycinnamate: An Active Anti-Metastasis Agent and Chemosensitizer Targeting NFKB from Kaempferia galanga for Melanoma Cells. Life (Basel). 2022 Mar 24;12(4):337.

[5]. Dual action effects of ethyl-p-methoxycinnamate against dengue virus infection and inflammation via NF-kB pathway suppression. Sci Rep. 2024 Apr 23;14(1):9322.

[6]. Ethyl p-methoxycinnamate inhibits tumor growth by suppressing fatty acid synthesis and depleting ATP. Sci Rep. 2025 May 2;15(1):15317.

[7]. Cytotoxic and Pro-Apoptotic Properties of Ethyl-p-Methoxycinnamate and Its Hydrophilic Derivative Potassium-p-Methoxycinnamate. Chemistry Africa. 2018 Jul 31;1(1-2):87-95.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C12H14O3
Molecular Weight
206.24
Exact Mass
206.094
CAS #
1929-30-2
Related CAS #
(E)-Ethyl p-methoxycinnamate; 24393-56-4
PubChem CID
5281783
Appearance
Typically exists as solids at room temperature
Melting Point
49 - 50 °C
Hydrogen Bond Donor Count
0
Rotatable Bond Count
5
Heavy Atom Count
15
Complexity
215
Defined Atom Stereocenter Count
0
SMILES
CCOC(=O)/C=C/C1=CC=C(C=C1)OC
InChi Key
DHNGCHLFKUPGPX-RMKNXTFCSA-N
InChi Code
InChI=1S/C12H14O3/c1-3-15-12(13)9-6-10-4-7-11(14-2)8-5-10/h4-9H,3H2,1-2H3/b9-6+
Chemical Name
ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
Synonyms
Ethyl p-methoxycinnamate
HS Tariff Code
2934.99.9001
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)
Solubility Data
Solubility (In Vitro)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*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 : PEG300Tween 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).
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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)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL 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).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.8487 mL 24.2436 mL 48.4872 mL
5 mM 0.9697 mL 4.8487 mL 9.6974 mL
10 mM 0.4849 mL 2.4244 mL 4.8487 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.

Calculator

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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