3579-85-9

Basic information

• Product Name: N-(4-hydroxyphenyl)cinnamamide
• Synonyms: N-(4-hydroxyphenyl)cinnamamide;N-(4-Hydroxyphenyl)-3-Phenyl-2-Propenamide;N-(4-Hydroxyphenyl)-3-phenylpropenamide
• CAS NO: 3579-85-9
• Molecular Formula: C₁₅H₁₃NO₂
• Molecular Weight: 239.26922
• EINECS: 222-701-2
• Mol File: 3579-85-9.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 495.4°Cat760mmHg
• Flash Point: 253.4°C
• Appearance: /
• Density: 1.26g/cm³
• Vapor Pressure: 1.94E-10mmHg at 25°C
• Refractive Index: 1.698
• CAS DataBase Reference: N-(4-hydroxyphenyl)cinnamamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-hydroxyphenyl)cinnamamide(3579-85-9)
• EPA Substance Registry System: N-(4-hydroxyphenyl)cinnamamide(3579-85-9)

Safety Data

• Hazardous Substances Data: 3579-85-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H13NO2/c17-14-9-7-13(8-10-14)16-15(18)11-6-12-4-2-1-3-5-12/h1-11,17H,(H,16,18)/b11-6+

Upstream product

• 123-30-8 4-amino-phenol 
• 102-92-1 Cinnamoyl chloride 
• 102-92-1 cinnamoyl chloride 
• 538-56-7 3-phenylpropenoic anhydride 
• 140-10-3 (E)-3-phenylacrylic acid 
• 621-82-9 Cinnamic acid 
• 201230-82-2 carbon monoxide 
• 536-74-3 phenylacetylene 

Downstream Products

• 94042-54-3 2,6-bis(1-pyrrolidinylmethyl)-4-cinnamidophenol 

Relevant articles and documents

Simple Synthesis of Amides via Their Acid Chlorides in Aqueous TPGS-750-M

The technology of surfactant chemistry is employed for amide bond construction via the reaction of acyl chlorides with amines in 2 wt % TPGS-750-M aqueous solution. Specifically, this highly efficient method enables a chromatography-free scalable process and recycling of the TPGS-750-M solution.

Structure–activity relationship investigation of tertiary amine derivatives of cinnamic acid as acetylcholinesterase and butyrylcholinesterase inhibitors: compared with that of phenylpropionic acid, sorbic acid and hexanoic acid

In the present investigation, 48 new tertiary amine derivatives of cinnamic acid, phenylpropionic acid, sorbic acid and hexanoic acid (4d–6g, 10d–12g, 16d–18g and 22d–24g) were designed, synthesized and evaluated for the effect on AChE and BChE in vitro. The results revealed that the alteration of aminoalkyl types and substituted positions markedly influences the effects in inhibiting AChE. Almost of all cinnamic acid derivatives had the most potent inhibitory activity than that of other acid derivatives with the same aminoalkyl side chain. Unsaturated bond and benzene ring in cinnamic acid scaffold seems important for the inhibitory activity against AChE. Among them, compound 6g revealed the most potent AChE inhibitory activity (IC50 value: 3.64 μmol/L) and highest selectivity over BChE (ratio: 28.6). Enzyme kinetic study showed that it present a mixed-type inhibition against AChE. The molecular docking study suggested that it can bind with the catalytic site and peripheral site of AChE.

Synthesis and structure-activity relationship analysis of caffeic acid amides as selective matrix metalloproteinase inhibitors

Four series of acid amides were synthesized, and through measurement using a fluorogenic substrate assay with human recombinant MMP-1, MMP-2 and MMP-9, compound 3f showed considerable inhibitory activities against MMP-2, MMP-9 and the best selectivity over MMP-1. Preliminary structure-activity relationship analysis indicated that caffeic acid amides with electron-donating groups at para-position of amino phenyl group showed better inhibitory activities and selectivity than those with electron-withdrawing groups, and the presence of adjacent dihydroxy in the caffeoyl group was very important for the MMP-2 and MMP-9 inhibitory activities.