| Size | Price | Stock | Qty |
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| 50mg |
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| 100mg |
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| 500mg |
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| Other Sizes |
| Targets |
Ethyl trans-caffeate targets multiple pathways and enzymes. Its primary anti-inflammatory mechanism involves the inhibition of nuclear factor-kappa B (NF-κB) activation by preventing NF-κB from binding to DNA . It also directly inhibits the enzymatic activity of human pancreatic α-amylase and HMG-CoA reductase (HMGCR) . In addition, it suppresses the activity of phosphoinositide 3-kinase (PI3K), ERK1/2, and p38 kinase through direct binding .
Ethyl trans-caffeate targets the NF-κB signaling pathway and its downstream inflammatory mediators. It inhibits iNOS (inducible nitric oxide synthase), COX-2 (cyclooxygenase-2), and PGE2 (prostaglandin E2). The compound also prevents DNA single-strand breaks caused by H₂O₂. Its anti-carcinogenic properties suggest additional targets in cancer cells. |
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| ln Vitro |
Ethyl trans-caffeate exhibits a range of potent in vitro activities. It strongly inhibits lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW 264.7 macrophages, with an IC₅₀ of 5.5 μg/mL . It suppresses the expression of pro-inflammatory mediators iNOS and COX-2 at both the mRNA and protein levels, as well as PGE₂ production, without significant cytotoxicity at effective concentrations . Furthermore, it strongly inhibits the neoplastic transformation of JB6 Cl41 cells and suppresses PI3K, ERK1/2, and p38 kinase activities by direct binding . It also inhibits HMG-CoA reductase activity, demonstrating potential as a cholesterol-lowering agent .
In vitro, Ethyl trans-caffeate suppresses NF-κB activation and its downstream inflammatory mediators iNOS, COX-2, and PGE2. It prevents DNA single-strand breaks caused by H₂O₂. The compound exhibits anti-inflammatory, immunomodulatory, and anti-carcinogenic properties. It has been studied as a high-resolution structure representative of inhibitors complexed with human pancreatic α-amylase. |
| ln Vivo |
In animal studies, Ethyl trans-caffeate demonstrates significant anti-inflammatory and chemopreventive effects. Topical application on mouse skin drastically inhibits TPA-induced overexpression of COX-2 protein and exerts chemopreventive effects against skin carcinogenesis caused by solar UV exposure . It has also been shown to ameliorate collagen-induced arthritis by suppressing the Th1 immune response and exhibits antifibrotic activity in vivo . One study showed it significantly inhibits HMG-CoA reductase activity in rat liver, comparable to the standard drug simvastatin .
Specific in vivo activity data for Ethyl trans-caffeate are limited. It has been studied for its effects on NF-κB activation in mouse skin, where it inhibits NF-κB activation and its downstream inflammatory mediators. It is considered a promising natural compound for future applications in chronic liver disease and as a chemopreventive agent against UV-induced skin carcinogenesis. |
| Enzyme Assay |
Several non-cellular assays have characterized the enzyme inhibition of Ethyl trans-caffeate. The binding to human pancreatic α-amylase was studied by solving high-resolution X-ray crystal structures of the enzyme-inhibitor complex . The inhibition of HMG-CoA reductase (HMGCR) activity was investigated through an enzymatic method, comparing its inhibitory percentage to the control drug simvastatin . The inhibition of NF-κB-DNA binding was assessed using an electrophoretic mobility shift assay (EMSA), which showed that the compound prevents the transcription factor from binding to its DNA response element .
Typical in vitro assays for Ethyl trans-caffeate include NF-κB activation assays using reporter gene systems in cell lines. iNOS, COX-2, and PGE2 levels are measured by Western blot or ELISA. Antioxidant activity is assessed by measuring protection against H₂O₂-induced DNA damage. α-Amylase inhibition assays are performed using enzymatic activity measurements. |
| Cell Assay |
Cellular activity was assessed using various cell lines. For anti-inflammatory studies, RAW 264.7 murine macrophages were pre-treated with Ethyl trans-caffeate before stimulation with LPS. Nitric oxide production was measured using the Griess reaction, and cell viability was determined by MTT assay to confirm the effects were not due to cytotoxicity . The expression of iNOS, COX-2, and related signaling proteins (PI3K, ERK, p38) was analyzed by Western blot, and gene expression was assessed by RT-PCR . Chemopreventive activity was evaluated using the JB6 Cl41 mouse epidermal cell line, where the compound's ability to inhibit neoplastic transformation was measured .
Cellular assays for Ethyl trans-caffeate typically involve treating macrophages or other cell lines with the compound at concentrations ranging from 1-100 µM. NF-κB activation is assessed by reporter gene assays or by measuring iNOS, COX-2, and PGE2 levels. Cell viability is assessed by MTT assay. DNA damage is assessed by comet assay or other methods. |
| Animal Protocol |
Animal protocols vary based on the model. In a mouse skin inflammation model, female ICR mice were treated topically with Ethyl trans-caffeate for 30 minutes prior to a 4-hour TPA application, after which skin tissues were harvested for immunohistochemical analysis of COX-2 . In a rat model studying cholesterol reduction, the compound was administered to assess its effect on HMGCR activity in the liver, followed by analysis of serum glutamate oxalate transaminase (SGOT)/serum glutamate pyruvate transaminase (SGPT) levels and liver histology to evaluate toxicity . For in vivo experiments, the compound can be formulated in various vehicles, such as 10% DMSO, 40% PEG300, 5% Tween 80, and 45% saline for injection, or suspended in 0.5% carboxymethyl cellulose (CMC) for oral administration .
In vivo animal experiments for Ethyl trans-caffeate have been conducted in mouse skin models. The compound is applied topically or administered systemically, and NF-κB activation and inflammatory mediator levels are assessed in skin tissue. It is also studied in models of UV-induced skin carcinogenesis. |
| ADME/Pharmacokinetics |
Ethyl Caffeate was found to have little or no cytotoxicity to RAW 264.7 macrophages at concentrations of 10 μg/mL or below, as determined by MTT assay. At 5 μg/mL, >50% of cells remained viable. [1]
In MCF-7 cells, no cytotoxic effects were observed with ethyl caffeate treatment at concentrations of 10-100 μg/mL over 6 hours as determined by MTT assay. [1] Pharmacokinetic data for Ethyl trans-caffeate are limited. As a small phenolic ester with a molecular weight of 208.21 g/mol, it would be expected to have good oral bioavailability. The compound has a density of 1.271 g/cm³, a melting point of 147-148°C, and a boiling point of 148-149°C. Detailed ADME parameters are not available. |
| Toxicity/Toxicokinetics |
Toxicological data for Ethyl trans-caffeate are limited. As a natural phenolic compound, it is generally considered to have low toxicity. The hazard class is Xn with risk statements 36/37/38-22 and safety statements 26-36. Standard laboratory safety precautions should be followed.
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| References | |
| Additional Infomation |
Ethyl trans-caffeic acid is an ethyl ester formed by the condensation of the carboxyl group of trans-caffeic acid with ethanol. It possesses anti-inflammatory and antitumor activities. It is an alkyl caffeic acid ester and ethyl ester, functionally related to trans-caffeic acid. Ethyl caffeic acid has been reported in perilla, Himalayan sasanqua, and several other organisms with relevant data.
Ethyl trans-caffeate (Ethyl caffeate) is a natural phenolic ester from Bidens pilosa and Ferula assafoetida with anti-inflammatory, immunomodulatory, and anti-carcinogenic properties. It suppresses NF-κB activation and downstream iNOS, COX-2, and PGE2. It is a research compound for studying inflammation, cancer, and chronic liver disease. It is not approved for any clinical indication. |
| Molecular Formula |
C11H12O4
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|---|---|
| Molecular Weight |
208.21058
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| Exact Mass |
208.073
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| CAS # |
66648-50-8
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| Related CAS # |
Ethyl Caffeate;102-37-4
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| PubChem CID |
5317238
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
377.0±32.0 °C at 760 mmHg
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| Flash Point |
148.4±18.6 °C
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| Vapour Pressure |
0.0±0.9 mmHg at 25°C
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| Index of Refraction |
1.612
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| Source |
Originated from plants: Leguminosae Erythrophleum fordii Oliv.
Originated from plants: Compositae |
| LogP |
1.72
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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 |
4
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| Heavy Atom Count |
15
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| Complexity |
237
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CCOC(=O)/C=C/C1=CC(=C(C=C1)O)O
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| InChi Key |
WDKYDMULARNCIS-GQCTYLIASA-N
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| InChi Code |
InChI=1S/C11H12O4/c1-2-15-11(14)6-4-8-3-5-9(12)10(13)7-8/h3-7,12-13H,2H2,1H3/b6-4+
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| Chemical Name |
ethyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
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| Synonyms |
Ethyl caffeate; 102-37-4; ethyl trans-caffeate; Ethyl 3,4-dihydroxycinnamate; ...; 66648-50-8;
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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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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 (~480.3 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 | 4.8028 mL | 24.0142 mL | 48.0284 mL | |
| 5 mM | 0.9606 mL | 4.8028 mL | 9.6057 mL | |
| 10 mM | 0.4803 mL | 2.4014 mL | 4.8028 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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