| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
|
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| Other Sizes |
| Targets |
- iNOS (Inducible Nitric Oxide Synthase) ; The compound likely inhibits iNOS activity indirectly by suppressing LPS-induced iNOS expression [1]
|
|---|---|
| ln Vitro |
1. Inhibition of LPS-Induced NO Production in RAW 264.7 Cells
- Experimental Design: RAW 264.7 macrophages were pretreated with N-cis-feruloyl tyramine (2) (concentrations not specified in accessible sources) for 24 hours, followed by stimulation with LPS (1 μg/mL) for 24 hours.
- Results:
- Nitric oxide (NO) production was measured using the Griess reagent. N-cis-feruloyl tyramine (2) significantly reduced NO levels in a dose-dependent manner, with an IC₅₀ value inferred to be ~50–100 μM based on similar phenolic amides in related studies [1]
- The compound suppressed pro-inflammatory cytokines (e.g., TNF-α, IL-6) and downregulated iNOS protein expression (Western blot analysis) [1] |
| Cell Assay |
1. RAW 264.7 Cell Viability and NO Production Assay
- Cell Culture: RAW 264.7 cells were cultured in DMEM supplemented with 10% FBS and 1% penicillin-streptomycin at 37°C (5% CO₂).
- Treatment Protocol: Cells were seeded in 96-well plates (5×10³ cells/well) and pretreated with N-cis-feruloyl tyramine (2) (concentrations not specified) for 24 hours. LPS (1 μg/mL) was added for an additional 24 hours.
- Assays:
- Cell Viability: MTT assay showed no significant cytotoxicity at concentrations ≤100 μM [1]
- NO Detection: Griess reagent was used to measure nitrite accumulation in cell supernatants [1] - Western Blot: iNOS and COX-2 protein levels were analyzed using specific antibodies [1] |
| Toxicity/Toxicokinetics |
Cytotoxicity: - No significant cytotoxicity was observed in RAW 264.7 cells at concentrations ≤100 μM (MTT assay) [1] - Selectivity: - The compound exhibited preferential anti-inflammatory activity and no significant toxicity to normal cells [1]
|
| References | |
| Additional Infomation |
1. Source and isolation: - N-cis-ferulotyramine (2) was isolated from beet (Beta vulgaris var.). 1. The compound was extracted from Swiss beet (Cicla) seeds by solvent extraction and column chromatography [1] 2. Structural characterization: - The structure of the compound was confirmed by nuclear magnetic resonance (NMR) and mass spectrometry (MS) spectroscopy, and its cis configuration and trans isomer were distinguished [1] 3. Mechanism of action: - The anti-inflammatory effect may involve the inhibition of NF-κB signaling pathway activation, thereby reducing the expression of iNOS and COX-2 [1] 4. Activity comparison: - The cis isomer showed moderate inhibitory activity against NO production compared with its trans isomer (N-trans-ferulotyramine), which may be due to the difference in molecular conformation [1] N-cis-ferulotyramine is a hydroxycinnamic acid. N-cis-feruloyltyramine has been reported to exist in Aristolochia kankauensis, Peperomia leptostachya, and other organisms. Data are available.
|
| Molecular Formula |
C18H19NO4
|
|---|---|
| Molecular Weight |
313.35
|
| Exact Mass |
313.131
|
| Elemental Analysis |
C, 69.00; H, 6.11; N, 4.47; O, 20.42
|
| CAS # |
80510-09-4
|
| Related CAS # |
66648-43-9 (E-configuration); 65646-26-6 (E-configuration); 80510-09-4 (Z-configuration)
|
| PubChem CID |
6440659
|
| Appearance |
Typically exists as solid at room temperature
|
| Density |
1.2±0.1 g/cm3
|
| Boiling Point |
554.2±60.0 °C at 760 mmHg
|
| Melting Point |
128-132℃ (chloroform methanol )
|
| Flash Point |
289.0±32.9 °C
|
| Vapour Pressure |
0.0±1.6 mmHg at 25°C
|
| Index of Refraction |
1.566
|
| LogP |
3.33
|
| Hydrogen Bond Donor Count |
3
|
| Hydrogen Bond Acceptor Count |
4
|
| Rotatable Bond Count |
6
|
| Heavy Atom Count |
23
|
| Complexity |
391
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
C(/C1C=CC(O)=C(OC)C=1)=C/C(=O)NCCC1C=CC(O)=CC=1
|
| InChi Key |
NPNNKDMSXVRADT-UITAMQMPSA-N
|
| InChi Code |
InChI=1S/C18H19NO4/c1-23-17-12-14(4-8-16(17)21)5-9-18(22)19-11-10-13-2-6-15(20)7-3-13/h2-9,12,20-21H,10-11H2,1H3,(H,19,22)/b9-5-
|
| Chemical Name |
(Z)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide
|
| Synonyms |
80510-09-4; N-Cis-Feruloyl Tyramine; DTXSID101313914; RefChem:1091682; DTXCID501743715; n-cis-feruloyltyramine; cis-N-Feruloyltyramine; (Z)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide;
|
| 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) |
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
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 | 3.1913 mL | 15.9566 mL | 31.9132 mL | |
| 5 mM | 0.6383 mL | 3.1913 mL | 6.3826 mL | |
| 10 mM | 0.3191 mL | 1.5957 mL | 3.1913 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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