106005-97-4

Basic information

• Product Name: 2-Propenamide, N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(4-hydroxyphenyl)-
• CAS NO: 106005-97-4
• Molecular Formula: C17H17NO4
• Molecular Weight: 299.326
• Mol File: 106005-97-4.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 2-Propenamide, N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(4-hydroxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenamide, N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(4-hydroxyphenyl)-(106005-97-4)
• EPA Substance Registry System: 2-Propenamide, N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(4-hydroxyphenyl)-(106005-97-4)

Safety Data

• Hazardous Substances Data: 106005-97-4(Hazardous Substances Data)

Upstream product

• 3943-97-3 methyl 4-hydroxycinnamate 
• 645-31-8 3-hydroxytyramine hydrobromide 
• 7400-08-0 p-Coumaric Acid 
• 123-08-0 4-hydroxy-benzaldehyde 
• 51-61-6 dopamine 
• 62-31-7 dopamine hydrochloride 
• 27542-85-4 4-acetoxycinnamic acid 

Relevant articles and documents

Method for synthesizing coumaroyl dopamine by one-pot method

The invention discloses a method for synthesizing coumaroyl dopamine by one-pot method, which comprises the following steps: (1) reacting coumaric acid serving as a raw material with ethyl chloroformate under the action of triethylamine to obtain an intermediate III; (2) carrying out condensation on the intermediate III and dopamine hydrochloride under the action of triethylamine to obtain an intermediate V; and (3) treating the intermediate V with hydrazine hydrate to obtain a target compound I, namely coumaroyl dopamine. The method has the advantages of high efficiency and high yield, and is suitable for large-scale industrial production.

Preparation method of N-coumaroyldopamine

The invention discloses a preparation method of N-coumaroyldopamine. The preparation method includes adding 3-hydroxytyramine hydrobromide, methyl p-hydroxycinnamate, and alkaline into a four-port round-bottom flask as well as solvent, stirring, and finishing thin-layer chromatography detection reaction; adding water into reaction solution to separate, adding ethyl acetate for extraction, washing organic phase with saturated salt solution, washing inorganic phase with diluted hydrochloric acid, drying with anhydrous sodium sulfate, filtering, and concentrating to obtain pulp; adding petroleum ether into the pulp, heating to reflow, cooling and standing, pouring solution on the upper layer, adding ethyl acetate into the pulp, mixing, filtering and drying to obtain white solids. Through authentication of nuclear magnetism, the product is N-coumaroyldopamine. In the preparation method of N-coumaroyldopamine, the final product is synthesized directly at one step, synthesis steps are greatly reduced, and production cost is greatly reduced. Moreover, fewer steps facilitate after-treatment of reaction, and purification is simplified.

Synthesis of phenolic amides and evaluation of their antioxidant and anti-inflammatory activity in vitro and in vivo

A series of 15 phenolic amides (PAs) have been synthesized (PA1-PA15) and examined in vitro by four different tests: (1) prevention of Cu2+-induced human low-density lipoprotein oxidation, (2) scavenging of stable radicals, (3) anti-inflammatory activity, (4) scavenging of superoxide radicals. We used PA1 and α-tocopherol for an in vivo study. The overall potential of the antioxidant system was significantly enhanced by the PA1 and α-tocopherol supplements as the hepatic TBARS levels were lowered while the hepatic SOD activities and GSH concentration were elevated in PA1 fed rats. Our results support that PA1 may exert antioxidant action through inhibiting superoxide generation. PA1 decreased the level of nitric oxide (NO) production, tumor necrosis factor-alpha (TNF-α) and nuclear factor-kappa B (NF-κB). These results show that PA1 can inhibit lipid peroxidation, enhance the activities of antioxidant enzymes, and decrease the TNF-α/NF-κB level and nitric oxide production. Therefore, it was speculated that PA1 acts through its anti-inflammation capacity.