N-cis-Feruloyl tyramine (cis-N-(4-Hydroxypheneth) ferulamide) is a natural phenolic compound with moderate inhibitory activity on LPS-activated NO production in RAW 264.7 cells.

Physicochemical Properties

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)

Biological Activity

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 showed preferential anti-inflammatory activity without overt toxicity to normal cells [1]
References	[1]. Inhibitory phenolic amides on lipopolysaccharide-induced nitric oxide production in RAW 264.7 cells from Beta vulgaris var. cicla seeds. Phytother Res. 2003 Sep;17(8):983-5.
Additional Infomation	1. Source and Isolation: - N-cis-feruloyl tyramine (2) was isolated from Beta vulgaris var. cicla (Swiss chard) seeds using solvent extraction and column chromatography [1] 2. Structural Characterization: - The compound’s structure was confirmed by NMR and MS spectroscopy, distinguishing its cis-configuration from the trans-isomer [1] 3. Mechanism of Action: - The anti-inflammatory effect likely involves suppression of NF-κB signaling pathway activation, leading to reduced iNOS and COX-2 expression [1] 4. Comparative Activity: - Compared to its trans-isomer (N-trans-feruloyl tyramine), the cis-form exhibited moderate inhibitory activity against NO production, possibly due to differences in molecular conformation [1] N-cis-Feruloyltyramine is a hydroxycinnamic acid. n-cis-Feruloyltyramine has been reported in Aristolochia kankauensis, Peperomia leptostachya, and other organisms with data available.

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 : 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). 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 : PEG300：Tween 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). 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	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.