66648-43-9

Basic information

• Product Name: N-Trans-Feruloyltyramine
• Synonyms: N-Trans-Feruloyltyramine;(E)-3-(4-hydroxy-3-Methoxy-phenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enaMide
• CAS NO: 66648-43-9
• Molecular Formula: C₁₈H₁₉NO₄
• Molecular Weight: 313
• Mol File: 66648-43-9.mol
• Article Data: 19

Chemical Properties

• Melting Point: 138-140 °C(Solv: chloroform (67-66-3); methanol (67-56-1))
• Boiling Point: 603.3°Cat760mmHg
• Flash Point: 318.7°C
• Appearance: /
• Density: 1.248g/cm³
• Vapor Pressure: 3.78E-15mmHg at 25°C
• Refractive Index: 1.636
• Storage Temp.: ?20°C
• PKA: 9.83±0.31(Predicted)
• CAS DataBase Reference: N-Trans-Feruloyltyramine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Trans-Feruloyltyramine(66648-43-9)
• EPA Substance Registry System: N-Trans-Feruloyltyramine(66648-43-9)

Safety Data

• Hazard Codes: N
• Statements: 50
• Safety Statements: 61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 66648-43-9(Hazardous Substances Data)

Usage

General Description

N-Trans-Feruloyltyramine is a natural phenolic compound found in various plants, including fruits, vegetables, and grains. It is known for its antioxidant and anti-inflammatory properties, making it a potential candidate for pharmaceutical and cosmetic applications. Studies have shown that N-Trans-Feruloyltyramine can protect cells from oxidative stress and reduce inflammation, making it a promising compound for the treatment of various health conditions. Additionally, it is also being researched for its potential use in skincare products due to its ability to protect the skin from UV-induced damage and aging. Overall, N-Trans-Feruloyltyramine is a versatile chemical with potential therapeutic and cosmetic benefits.

InChI:InChI=1/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+

Synthetic route

tyrosamine (51-67-2) + (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) → (E)-N-feruloyltyramine (66648-43-9)

Conditions	Yield
With diethyl cyanophosphonate In N,N-dimethyl-formamide at 0℃; for 6h;	80%
Stage #1: (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid With triethylamine In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: tyrosamine With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 20.5h;	73%
Stage #1: (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: tyrosamine With triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; Inert atmosphere;	58%

N,O-di-(trans-acetylferuloyl)-tyramine (76733-94-3) → (E)-N-feruloyltyramine (66648-43-9)

Conditions	Yield
With potassium hydroxide In methanol Ambient temperature;	57.5%

Acetic acid 4-{(E)-2-[2-(4-hydroxy-phenyl)-ethylcarbamoyl]-vinyl}-2-methoxy-phenyl ester → (E)-N-feruloyltyramine (66648-43-9)

Conditions	Yield
With sodium carbonate In ethanol for 2h; Heating; Yield given;
With hydrazine hydrate In acetonitrile at 20℃;	0.17 g

tyrosamine (51-67-2) + 2,5-dioxopyrrolidin-1-yl (E)-3-(4-hydroxy-3-methoxyphenyl)acrylate (56254-05-8) → (E)-N-feruloyltyramine (66648-43-9)

Conditions	Yield
With sodium hydrogencarbonate In water; acetone for 24h;

tyrosamine (51-67-2) + caffeic acid coenzyme A thiol ester (1021913-49-4) → (E)-N-feruloyltyramine (66648-43-9)

Conditions	Yield
With tyramine N-hydroxycinnamoyltransferase; tris hydrochloride In water at 30℃; pH=8.5; Enzyme kinetics; Acylation; Enzymatic reaction;

tyrosamine (51-67-2) + 4-coumaroyl-coenzyme A (30802-00-7, 119785-99-8) → (E)-N-feruloyltyramine (66648-43-9)

Conditions	Yield
With tyramine N-hydroxycinnamoyltransferase; tris hydrochloride In water at 30℃; pH=8.5; Enzyme kinetics; Acylation; Enzymatic reaction;

tyrosamine (51-67-2) + feruloyl-CoA (30802-02-9, 142185-30-6) → (E)-N-feruloyltyramine (66648-43-9)

Conditions	Yield
With tyramine N-hydroxycinnamoyltransferase; tris hydrochloride In water at 30℃; pH=8.5; Enzyme kinetics; Acylation; Enzymatic reaction;

tyrosamine (51-67-2) + sinapoyl-CoA (54429-80-0) → (E)-N-feruloyltyramine (66648-43-9)

Conditions	Yield
With tyramine N-hydroxycinnamoyltransferase; tris hydrochloride In water at 30℃; pH=8.5; Enzyme kinetics; Acylation; Enzymatic reaction;

tyrosamine (51-67-2) → (E)-N-feruloyltyramine (66648-43-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2 / 20 °C 2: 0.17 g / hydrazine monohydrate / acetonitrile / 20 °C View Scheme
Multi-step reaction with 2 steps 1: tetrahydrofuran / 6 h / Heating 2: 57.5 percent / KOH / methanol / Ambient temperature View Scheme

4-acetoxy-3-methoxycinnamoyl chloride (50906-12-2) → (E)-N-feruloyltyramine (66648-43-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2 / 20 °C 2: 0.17 g / hydrazine monohydrate / acetonitrile / 20 °C View Scheme
Multi-step reaction with 2 steps 1: tetrahydrofuran / 6 h / Heating 2: 57.5 percent / KOH / methanol / Ambient temperature View Scheme

(E)-3-(4-acetoxy-3-methoxyphenyl)acrylic acid (2596-47-6, 147677-05-2, 34749-55-8) → (E)-N-feruloyltyramine (66648-43-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: thionyl chloride / benzene; tetrahydrofuran / 2 h / Heating 2: tetrahydrofuran / 6 h / Heating 3: 57.5 percent / KOH / methanol / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: Et3N / tetrahydrofuran 2: Et3N / tetrahydrofuran / Ambient temperature 3: 3percent aq. Na2CO3 / ethanol / 2 h / Heating View Scheme

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) → (E)-N-feruloyltyramine (66648-43-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: pyridine 2: Et3N / tetrahydrofuran 3: Et3N / tetrahydrofuran / Ambient temperature 4: 3percent aq. Na2CO3 / ethanol / 2 h / Heating View Scheme

Acetic acid 4-((E)-3-isobutoxycarbonyloxy-3-oxo-propenyl)-2-methoxy-phenyl ester → (E)-N-feruloyltyramine (66648-43-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / Ambient temperature 2: 3percent aq. Na2CO3 / ethanol / 2 h / Heating View Scheme

2-methoxy-4-iodophenol (203861-62-5) + N-(4-hydroxyphenethyl)acrylamide (80633-44-9) → (E)-N-feruloyltyramine (66648-43-9)

Conditions	Yield
With tetrabutylammomium bromide; palladium diacetate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 130 - 140℃; Heck reaction; Microwave irradiation; Continuous-flow conditions;	1.64 g

cis-ferulic acid (1014-83-1) + tyramine hydrochloride (60-19-5) → (E)-N-feruloyltyramine (66648-43-9)

Conditions	Yield
With triethylamine; lipase In acetonitrile at 40℃; for 48h; Reagent/catalyst; Temperature; Time; Sealed tube;

(Z)-N-feruloyltyramine (65646-26-6, 66648-43-9, 80510-09-4) → (E)-N-feruloyltyramine (66648-43-9)

Conditions	Yield
In methanol for 96h; Kinetics; UV-irradiation;

(E)-N-feruloyltyramine (66648-43-9) + acetic anhydride (108-24-7) → N-trans-feruloyal tyramine diacetate (66648-46-2)

Conditions	Yield
With pyridine	70%
In pyridine
With pyridine Ambient temperature; Yield given;
With pyridine Yield given;
With pyridine for 24h; Ambient temperature;	10.3 mg

(E)-N-feruloyltyramine (66648-43-9) → (±)-trans-grossamide + 7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-N2,N3-bis(4-hydroxyphenethyl)-6-methoxy-1,2-dihydronaphthalene-2,3-dicarboxamide

Conditions	Yield
With dihydrogen peroxide; horseradish peroxidase In ethanol at 37℃; for 24h; pH 7.4; further reagents and conditions;	A 18% B 10%

(E)-N-feruloyltyramine (66648-43-9) → (±)-trans-grossamide

Conditions	Yield
With Trametes versicolor laccase In ethyl acetate at 25℃; for 4h; pH=4.5; Green chemistry; Enzymatic reaction; diastereoselective reaction;	16%

(E)-N-feruloyltyramine (66648-43-9) → tyramine hydrochloride (60-19-5)

Conditions	Yield
With hydrogenchloride In ethanol for 20h; Heating;	15 mg

(E)-N-feruloyltyramine (66648-43-9) → (Z)-N-feruloyltyramine (65646-26-6, 66648-43-9, 80510-09-4)

Conditions	Yield
In methanol for 2h; Ambient temperature; Irradiation; Yield given;
In methanol for 96h; Kinetics; UV-irradiation;

(E)-N-feruloyltyramine (66648-43-9) + acetic anhydride (108-24-7) → N-dihydroferuloyl tyramine diacetate

Conditions	Yield
With hydrogen; palladium on activated charcoal 1.) MeOH; 2.) pyridine; Yield given. Multistep reaction;

(E)-N-feruloyltyramine (66648-43-9) + methyl iodide (74-88-4) → (E)-3-(3,4-dimethoxyphenyl)-N-(4-methoxyphenethyl)acrylamide

Conditions	Yield
With sodium methylate In methanol Ambient temperature; Yield given;

(E)-N-feruloyltyramine (66648-43-9) → cannabisin G + cannabisin F + cannabisin E

Conditions	Yield
With iron(III) chloride In acetone for 48h; Ambient temperature;	A 14 mg B n/a C 22 mg

N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide (24589-78-4) + (E)-N-feruloyltyramine (66648-43-9) → (E)-3-(3-Methoxy-4-trimethylsilanyloxy-phenyl)-N-[2-(4-trimethylsilanyloxy-phenyl)-ethyl]-acrylamide

Conditions	Yield
at 85℃; for 0.25h;

(E)-N-feruloyltyramine (66648-43-9) → (-)-cannabasin B

Conditions	Yield
Multi-step reaction with 2 steps 1: 10 percent / horseradish peroxidase, H2O2 (0.06percent) / ethanol / 24 h / 37 °C / pH 7.4; further reagents and conditions 2: 63 percent / LiI / hexamethylphosphoric acid triamide / 3 h / 150 °C View Scheme

(E)-N-feruloyltyramine (66648-43-9) → cannabisin F

Conditions	Yield
Multi-step reaction with 2 steps 1: 22 mg / aq. FeCl3 / acetone / 48 h / Ambient temperature 2: 5 mg / H2SO4 / tetrahydrofuran / Heating View Scheme

(E)-N-feruloyltyramine (66648-43-9) → trans-grossamide (80510-06-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 2 h / Ambient temperature; Irradiation 2: 20 percent / 0.022percent H2O2 / 18 h / 38 °C / peroxidase, phosphate buffer sulution (pH 7.38) View Scheme

(E)-N-feruloyltyramine (66648-43-9) → N-cis-feruloyl tyramine diacetate (80510-10-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 2 h / Ambient temperature; Irradiation 2: pyridine View Scheme

(E)-N-feruloyltyramine (66648-43-9) → methyl 2-<2-hydroxy-3-methoxy-5-(2-methyloxycarbonylethyl)phenyl>-3-(4-hydroxy-3-methoxyphenyl)acrylate

Conditions	Yield
Multi-step reaction with 4 steps 1: methanol / 2 h / Ambient temperature; Irradiation 2: 20 percent / 0.022percent H2O2 / 18 h / 38 °C / peroxidase, phosphate buffer sulution (pH 7.38) 3: H2 / 10percent Pd-C / ethanol / 2 h 4: 1.) 6 N aq. HCl, 2.) HCl / 1.) 8.5 h, reflux, 2.) 2 h, reflux View Scheme

(E)-N-feruloyltyramine (66648-43-9) → dihydrogrossamide (80510-13-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: methanol / 2 h / Ambient temperature; Irradiation 2: 20 percent / 0.022percent H2O2 / 18 h / 38 °C / peroxidase, phosphate buffer sulution (pH 7.38) 3: H2 / 10percent Pd-C / ethanol / 2 h View Scheme

(E)-N-feruloyltyramine (66648-43-9) → triacetyl grossamide

Conditions	Yield
Multi-step reaction with 3 steps 1: methanol / 2 h / Ambient temperature; Irradiation 2: 20 percent / 0.022percent H2O2 / 18 h / 38 °C / peroxidase, phosphate buffer sulution (pH 7.38) 3: pyridine View Scheme

Upstream product

• 51-67-2 tyrosamine 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 76733-94-3 N,O-di-(trans-acetylferuloyl)-tyramine 
• 56254-05-8 ferulic acid N-hydroxysuccinimidyl ester 
• 1021913-49-4 caffeic acid coenzyme A thiol ester 
• 30802-00-7 4-coumaroyl-coenzyme A 
• 30802-02-9 feruloyl-CoA 
• 54429-80-0 sinapoyl-CoA 
• 50906-12-2 4-acetoxy-3-methoxycinnamoyl chloride 
• 2596-47-6 (E)-3-(4-acetoxy-3-methoxyphenyl)acrylic acid 
• 203861-62-5 2-methoxy-4-iodophenol 
• 80633-44-9 N-(4-hydroxyphenethyl)acrylamide 
• 1014-83-1 cis-ferulic acid 
• 60-19-5 tyramine hydrochloride 

Downstream Products

• 60-19-5 tyramine hydrochloride 
• 65646-26-6 (Z)-N-feruloyltyramine 
• 66648-46-2 N-trans-feruloyal tyramine diacetate 
• 80510-06-1 trans-grossamide 
• 163136-19-4 cannabisin F 
• 187655-56-7 (±)-trans-grossamide 
• 144506-19-4 7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-N₂,N₃-bis(4-hydroxyphenethyl)-6-methoxy-1,2-dihydronaphthalene-2,3-dicarboxamide 
• 80510-10-7 N-cis-feruloyl tyramine diacetate 
• 80510-13-0 dihydrogrossamide 

Relevant articles and documents

Lipase catalysed synthesis of N-trans-feruloyltyramine and a quantitative HPLC-UV method for analysis

N-trans feruloyltyramine amide was successfully synthesized from 4-hydroxy-3-methoxycinnamic acid and tyramine hydrochloride in a one-step lipase catalysed reaction. The use of immobilized lipase, lipozyme TL IM as the catalyst in the reaction allowed simple isolation of the enzyme from the products and other components in the reaction mixture. N-feruloyltyramine amide was characterized using Fourier Transform Infrared (FTIR) Spectroscopy, Proton Nuclear Magnetic Resonance (1H NMR) and elemental analysis. Under optimized conditions 93.5% yield was obtained when the process was carried out for 48 h using a molar ratio of cinnamic acid:tyramine HCl, 6:1 at 40°C. In addition, a rapid simple and sensitive HPLC-UV method was developed for the determination of N-feruloyltyramine using an Rp-8 endcapped column. The optimum mobile phase used was acetonitrile:disodium hydrogen phosphate, 30:70(v/v.). N-feruloyltyramine amide was detected at a retention time of 12 min. The calibration curve was linear over the range of 5.2712.30 × 10-4 M with correlation factor r 0.9958. Consequently, the method was considered valid for quantitative analysis samples of N-trans-feruloyltyramine amide.

Identification and quantification of potential anti-inflammatory hydroxycinnamic acid amides from wolfberry

Wolfberry or Goji berry, the fruit of Lycium barbarum, exhibits health-promoting properties that leads to an extensive study of their active components. We synthesized a set of hydroxycinnamic acid amide (HCCA) compounds, including trans-caffeic acid, trans-ferulic acid, and 3,4-dihydroxyhydrocinnamic acid, with extended phenolic amine components as standards to identify and quantify the corresponding compounds from wolfberry and to investigate anti-inflammatory properties of these compounds using in vitro model. With optimized LC-MS/MS and NMR analysis, nine amide compounds were identified from the fruits. Seven of these compounds were identified in this plant for the first time. The amide compounds with a tyramine moiety were the most abundant. In vitro studies indicated that five HCCA compounds showed inhibitory effect on NO production inuded by lipopolysaccharides with IC50 less than 15.08 μM (trans-N-feruloyl dopamine). These findings suggested that wolfberries demonstrated anti-inflammatory properties.

Dihydrobenzofuran Neolignanamides: Laccase-Mediated Biomimetic Synthesis and Antiproliferative Activity

The biomimetic synthesis of a small library of dihydrobenzofuran neolignanamides (the natural trans-grossamide (4) and the related compounds 21-28) has been carried out through an eco-friendly oxidative coupling reaction mediated by Trametes versicolor laccase. These products, after complete spectroscopic characterization, were evaluated for their antiproliferative activity against Caco-2 (colon carcinoma), MCF-7 (mammary adenocarcinoma), and PC-3 (prostate cancer) human cells, using an MTT bioassay. The racemic neolignamides (±)-21 and (±)-27, in being the most lipophilic in the series, were potently active, with GI50 values comparable to or even lower than that of the positive control 5-FU. The racemates were resolved through chiral HPLC, and the pure enantiomers were subjected to ECD measurements to establish their absolute configurations at C-2 and C-3. All enantiomers showed potent antiproliferative activity, with, in particular, a GI50 value of 1.1 μM obtained for (2R,3R)-21. The effect of (±)-21 on the Caco-2 cell cycle was evaluated by flow cytometry, and it was demonstrated that (±)-21 exerts its antiproliferative activity by inducing cell cycle arrest and apoptosis.