138343-04-1

Basic information

• Product Name: 2-Propenamide, 3-(3,4-dihydroxyphenyl)-N-ethyl-, (2E)- (9CI)
• Synonyms: 2-Propenamide, 3-(3,4-dihydroxyphenyl)-N-ethyl-, (2E)- (9CI)
• CAS NO: 138343-04-1
• Molecular Formula: C₁₁H₁₃NO₃
• Molecular Weight: 207.22582
• Product Categories: ALCOHOL
• Mol File: 138343-04-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Propenamide, 3-(3,4-dihydroxyphenyl)-N-ethyl-, (2E)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenamide, 3-(3,4-dihydroxyphenyl)-N-ethyl-, (2E)- (9CI)(138343-04-1)
• EPA Substance Registry System: 2-Propenamide, 3-(3,4-dihydroxyphenyl)-N-ethyl-, (2E)- (9CI)(138343-04-1)

Safety Data

• Hazardous Substances Data: 138343-04-1(Hazardous Substances Data)

Usage

Chemical Class

Phenylpropanoids

Derivative of

3-(3,4-dihydroxyphenyl)prop-2-enal

Primary Use

Pharmaceutical and cosmetic industries

Properties

Potential antioxidant and anti-inflammatory properties

Applications

Treatment of neurodegenerative diseases
Anti-aging agent in skin care products

Upstream product

• 331-39-5 caffeic acid 
• 75-04-7 ethylamine 
• 331-39-5 caffeic acid 

Relevant articles and documents

Identification of cinnamic acid derivatives as novel antagonists of the prokaryotic proton-gated ion channel GLIC

Pentameric ligand gated ion channels (pLGICs) mediate signal transduction. The binding of an extracellular ligand is coupled to the transmembrane channel opening. So far, all known agonists bind at the interface between subunits in a topologically conserved "orthosteric site" whose amino acid composition defines the pharmacological specificity of pLGIC subtypes. A striking exception is the bacterial proton-activated GLIC protein, exhibiting an uncommon orthosteric binding site in terms of sequence and local architecture. Among a library of Gloeobacter violaceus metabolites, we identified a series of cinnamic acid derivatives, which antagonize the GLIC proton-elicited response. Structure-activity analysis shows a key contribution of the carboxylate moiety to GLIC inhibition. Molecular docking coupled to site-directed mutagenesis support that the binding pocket is located below the classical orthosteric site. These antagonists provide new tools to modulate conformation of GLIC, currently used as a prototypic pLGIC, and opens new avenues to study the signal transduction mechanism.

Synthesis, structure and structure-activity relationship analysis of caffeic acid amides as potential antimicrobials

A series of caffeic acid amides 1-23 were synthesized and nine of which (13-17, 19-21 and 23) were reported for the first time. The chemical structures of these compounds were confirmed by means of 1H NMR, ESI MS and elemental analyses. Compound 15 was determined by single-crystal X-ray diffraction analysis. All of the compounds were assayed for antibacterial (Bacillus subtilis, Escherichia coli, Pseudomonas fluorescens and Staphylococcus aureus) and antifungal (Aspergillus niger, Candida albicans and Trichophyton rubrum) activities by MTT method. Compounds 10-12, 15, 18 and 21 showed considerable antibacterial activities against B. subtilis with MICs of 7.95, 6.25, 3.89, 1.18, 3.12 and 15.5?μg/mL, respectively. Structure-activity relationship analysis disclosed that caffeic acid anilides with electron-donating groups at p-position of benzene ring have better inhibitory activities.

Synthesis and evaluation of caffeic acid amides as antioxidants

A series of amides of caffeic acid has been synthesised and their antioxidant properties evaluated as lipid peroxidation inhibitors. Anilides of caffeic acid were found to be very efficient antioxidants with IC50's of 0.3 μM.