103188-49-4

Basic information

• Product Name: (e)-3-(3,4-dihydroxyphenyl)-n-(2-(3,4-dihydroxyphenyl)ethyl)-2-propenaMide
• Synonyms: (E)-N-(3,4-Dihydroxyphenethyl)-3-(3,4-dihydroxyphenyl)acrylaMide;N-caffeoyldopaMine;Caffenoyldopamine;3-(3,4-dihydroxyphenyl)-N-[2-(3,4-dihydroxyphenyl)ethyl]prop-2-enamide;(e)-3-(3,4-dihydroxyphenyl)-n-(2-(3,4-dihydroxyphenyl)ethyl)-2-propenaMide;N-(3,4-dihydroxyphenethyl)-3-(3,4-dihydroxyphenyl)acrylaMide;(e)-3-(3;4-dihydroxyphenyl)ethyl)-2-propenaMide
• CAS NO: 103188-49-4
• Molecular Formula: C₁₇H₁₇NO₅
• Molecular Weight: 315.32058
• Mol File: 103188-49-4.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 691.222 °C at 760 mmHg
• Flash Point: 371.838 °C
• Appearance: /
• Density: 1.409
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.706
• Storage Temp.: 2-8°C
• PKA: 9.38±0.10(Predicted)
• CAS DataBase Reference: (e)-3-(3,4-dihydroxyphenyl)-n-(2-(3,4-dihydroxyphenyl)ethyl)-2-propenaMide(CAS DataBase Reference)
• NIST Chemistry Reference: (e)-3-(3,4-dihydroxyphenyl)-n-(2-(3,4-dihydroxyphenyl)ethyl)-2-propenaMide(103188-49-4)
• EPA Substance Registry System: (e)-3-(3,4-dihydroxyphenyl)-n-(2-(3,4-dihydroxyphenyl)ethyl)-2-propenaMide(103188-49-4)

Safety Data

• Hazardous Substances Data: 103188-49-4(Hazardous Substances Data)

Usage

General Description

"(e)-3-(3,4-dihydroxyphenyl)-n-(2-(3,4-dihydroxyphenyl)ethyl)-2-propenaMide" is a chemical compound that belongs to the family of propenamides. It is a small molecule composed of three aromatic hydroxyl groups and an amide functional group, giving it potential pharmaceutical and biological activity. (e)-3-(3,4-dihydroxyphenyl)-n-(2-(3,4-dihydroxyphenyl)ethyl)-2-propenaMide may have antioxidant, anti-inflammatory, and potentially anticancer properties due to its structural characteristics. Further research and studies are needed to fully understand the potential uses and effects of this chemical compound.

InChI:InChI=1/C17H17NO5/c19-13-4-1-11(9-15(13)21)3-6-17(23)18-8-7-12-2-5-14(20)16(22)10-12/h1-6,9-10,19-22H,7-8H2,(H,18,23)/b6-3+

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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

Synthesis of amide and ester derivatives of cinnamic acid and its analogs: Evaluation of their free radical scavenging and monoamine oxidase and cholinesterase inhibitory activities

A series of cinnamic acid derivatives, amides (1–12) and esters (13–22), were synthesized, and structure–activity relationships for antioxidant activity, and monoamine oxidases (MAO) A and B, acetylcholinesterase, and butyrylcholinesterase (BChE) inhibitory activities were analyzed. Among the synthesized compounds, compounds 1–10, 12–18, and rosmarinic acid (23), which contained catechol, o-methoxyphenol or 5-hydroxy-indole moieties, showed potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity. Compounds 9–11, 15, 17–22 showed potent and selective MAO-B inhibitory activity. Compound 20 was the most potent inhibitor of MAO-B. Compounds 18 and 21 showed moderate BChE inhibitory activity. In addition, compound 18 showed potent antioxidant activity and MAO-B inhibitory activity. In a comparison of the cinnamic acid amides and esters, the amides exhibited more potent DPPH free radical scavenging activity, while the esters showed stronger inhibitory activities against MAO-B and BChE. These results suggested that cinnamic acid derivatives such as compound 18, p-coumaric acid 3,4-dihydroxyphenethyl ester, and compound 20, p-coumaric acid phenethyl ester, may serve as lead compounds for the development of novel MAO-B inhibitors and candidate lead compounds for the prevention or treatment of Alzheimer’s disease.

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.