142350-99-0

Basic information

• Product Name: 2-Propenamide, N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-, (E)-
• CAS NO: 142350-99-0
• Molecular Formula: C18H19NO5
• Molecular Weight: 329.353
• Mol File: 142350-99-0.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 2-Propenamide, N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenamide, N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-, (E)-(142350-99-0)
• EPA Substance Registry System: 2-Propenamide, N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-, (E)-(142350-99-0)

Safety Data

• Hazardous Substances Data: 142350-99-0(Hazardous Substances Data)

Usage

Molecular structure

Complex structure composed of a vinyl amide group attached to a phenethylamine moiety, which is linked to a resorcinol and a methoxyphenol group

Potential applications

Pharmaceuticals, development of new materials, bioactive compounds

Functional groups

Phenolic and amide, known for their biological activity

Need for further research

To fully understand the properties and potential uses of this compound.

Upstream product

• 51-61-6 dopamine 
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• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 62-31-7 dopamine hydrochloride 
• 121-33-5 vanillin 
• 2596-47-6 (E)-3-(4-acetoxy-3-methoxyphenyl)acrylic acid 

Relevant articles and documents

Acetylcholinesterase inhibition and antioxidant activity of N-trans-caffeoyldopamine and N-trans-feruloyldopamine

Phenolic acids and their derivatives found in nature are well-known for their potential biological activity. In this study, two amides derived from trans-caffeic/ferulic acid and dopamine were synthesized and characterized by Fourier-transform infrared sp

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.

Anti-tyrosinase, antioxidant and antimicrobial activities of hydroxycinnamoylamides

Synthetic hydroxycinnamoylamides of amino acids (precursors of aromatic amines) were studied for their antioxidant activity in vitro by two antioxidant assay systems, including 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and inhibition of lipid peroxidation (LPO). Furthermore, these compounds were tested and compared with their corresponding cinnamoylamides of aromatic amines for their inhibitory activity using mushroom tyrosinase. In addition, five hydroxycinnamoyl amino acid amides were investigated for their antimicrobial effect. Structure-activity relationships analysis disclosed that the presence of catechol rest at amino acid or at benzene moieties of substituted cinnamic acid amides significantly scavenged DPPH radical and inhibited LPO. The results obtained by LPO clearly expressed the positive influence of indole moiety on the activity. Moreover, the existence of p-hydroxy substituted cinnamic acid moiety leads to better tyrosinase inhibition. Amongst the tested compounds, amides of p-coumaroyldopamine or tyramine and their corresponding amino acid precursors are the most potent tyrosinase inhibitors.