| Size | Price | Stock | Qty |
|---|---|---|---|
| 25mg |
|
||
| 100mg |
|
||
| 250mg |
|
||
| 500mg |
|
||
| Other Sizes |
| Targets |
iNOS (inducible Nitric Oxide Synthase, IC50 = 25.6 μM for NO production inhibition) [1]
COX-2 (Cyclooxygenase-2, IC50 = 32.1 μM for PGE2 production inhibition) [1] |
|---|---|
| ln Vitro |
In LPS (1 μg/mL)-stimulated RAW264.7 murine macrophages, (E)-Ethyl p-methoxycinnamate (10-50 μM) exhibited dose-dependent anti-inflammatory activity. At 25.6 μM (IC50), it inhibited nitric oxide (NO) production by 50%; at 50 μM, NO inhibition rate reached 78%, as detected by Griess reagent assay [1]
It also suppressed prostaglandin E2 (PGE2) synthesis in a concentration-dependent manner: 32.1 μM (IC50) reduced PGE2 production by 50%, and 50 μM achieved a 72% inhibition rate, measured by sandwich ELISA [1] qPCR analysis showed that 50 μM of the compound downregulated iNOS mRNA expression by 68% and COX-2 mRNA expression by 63%. Western blot confirmed reduced protein levels: iNOS by 71% and COX-2 by 65% at 50 μM [1] Additionally, it inhibited the secretion of pro-inflammatory cytokines: TNF-α production was reduced by 67% and IL-6 by 61% at 50 μM. It showed no significant cytotoxicity to RAW264.7 cells at concentrations up to 100 μM (MTT assay: >92% viability) [1] |
| ln Vivo |
In ICR mice (20-25 g) with TPA (12-O-tetradecanoylphorbol-13-acetate)-induced ear edema, topical application of (E)-Ethyl p-methoxycinnamate (20 mg/kg or 40 mg/kg) 30 minutes before TPA challenge dose-dependently inhibited edema formation. The 20 mg/kg dose reduced ear swelling by 42%, and the 40 mg/kg dose by 65%, compared to the vehicle control group [1]
Histopathological examination of ear tissues revealed that the 40 mg/kg dose decreased inflammatory cell infiltration by 70%, reduced vascular dilation and edema, and diminished dermal thickness by 58% (H&E staining) [1] |
| Cell Assay |
RAW264.7 macrophage anti-inflammatory assay: RAW264.7 cells were cultured in DMEM supplemented with fetal bovine serum, seeded in 96-well plates (5×10⁴ cells/well) for NO/PGE2 detection or 6-well plates (2×10⁵ cells/well) for protein/mRNA analysis, and allowed to adhere for 24 hours [1]
Cells were pretreated with (E)-Ethyl p-methoxycinnamate (10-50 μM) for 1 hour, then stimulated with LPS (1 μg/mL) for 24 hours. Supernatants were collected for NO quantification (Griess reagent) and PGE2 detection (ELISA) [1] For protein extraction, cells were lysed with RIPA buffer, and iNOS/COX-2 protein levels were measured by Western blot (SDS-PAGE electrophoresis, membrane transfer, antibody incubation, ECL detection). For mRNA analysis, total RNA was extracted by Trizol method, reverse-transcribed to cDNA, and qPCR was performed to quantify iNOS/COX-2 mRNA expression (β-actin as internal control) [1] |
| Animal Protocol |
TPA-induced mouse ear edema model: Male ICR mice (20-25 g, n=6 per group) were randomly divided into control, model, 20 mg/kg, and 40 mg/kg treatment groups. (E)-Ethyl p-methoxycinnamate was dissolved in 5% DMSO + 95% ethanol to prepare 20 mg/mL and 40 mg/mL solutions, and 10 μL/ear was topically applied to the left ear of mice [1]
Thirty minutes later, the left ear of model and treatment groups was treated with TPA (2.5 μg/ear, dissolved in 20 μL acetone), while the right ear served as a control. Twenty-four hours after TPA challenge, ear thickness was measured with a vernier caliper, and edema rate was calculated as [(left ear thickness - right ear thickness)/right ear thickness × 100%] [1] Mice were euthanized, and left ear tissues were fixed in 4% paraformaldehyde, embedded in paraffin, sectioned, and stained with H&E for histological observation of inflammatory cell infiltration and tissue morphology [1] |
| Toxicity/Toxicokinetics |
In vitro toxicity: Ethyl (E)-p-methoxycinnamate at concentrations up to 100 μM did not show significant cytotoxicity to RAW264.7 cells (MTT assay: cell viability >92% vs. control group) [1] In vivo toxicity: Topical application of 40 mg/kg ethyl (E)-p-methoxycinnamate in ICR mice did not cause abnormal behavior, significant weight changes, or histopathological abnormalities of the liver, kidneys, or heart within 24 hours [1]
|
| References | |
| Additional Infomation |
4-Methoxycinnamate ethyl ester is a cinnamic ester. It has been reported that 4-methoxycinnamate ethyl ester exists in galangal and ginger flowers, and relevant data are available.
(E)-ethyl p-methoxycinnamate is a natural phenylpropanoid compound, which was isolated from the dried rhizome of Kaempferia galangal L. [1] The extraction method is to extract the crushed Kaempferia galangal rhizome by refluxing with 95% ethanol, concentrate the extract, and then purify it by silica gel column chromatography (petroleum ether-ethyl acetate gradient elution) and gel column chromatography [1] Its chemical structure was identified by spectroscopic analysis (UV, IR, ¹H-NMR, ¹³C-NMR, MS), and it was confirmed to be the trans isomer of ethyl p-methoxycinnamate [1] Its anti-inflammatory mechanism involves downregulating the mRNA and protein expression of iNOS and COX-2, thereby reducing the production of inflammatory mediators (NO, PGE2) and pro-inflammatory cytokines (TNF-α, IL-6) [1]. |
| Molecular Formula |
C12H14O3
|
|---|---|
| Molecular Weight |
206.2378
|
| Exact Mass |
206.094
|
| CAS # |
24393-56-4
|
| PubChem CID |
5281783
|
| Appearance |
Light yellow to yellow solid powder
|
| Density |
1.1±0.1 g/cm3
|
| Boiling Point |
325.1±17.0 °C at 760 mmHg
|
| Melting Point |
49ºC
|
| Flash Point |
133.8±15.5 °C
|
| Vapour Pressure |
0.0±0.7 mmHg at 25°C
|
| Index of Refraction |
1.540
|
| LogP |
2.65
|
| Hydrogen Bond Donor Count |
0
|
| Hydrogen Bond Acceptor Count |
3
|
| 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
|
| 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 (In Vitro) |
DMSO : ~100 mg/mL (~484.87 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (12.12 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 (12.12 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. 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 (12.12 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 | 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.
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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
