2979-06-8

Basic information

• Product Name: P-hydroxyl ethyl cinnaMate
• Synonyms: ETHYL-p-COUMARATE(P);2-Propenoic acid, 3-(4-hydroxyphenyl)-, ethyl ester;Ethyl p-coumarate;NSC 408777
• CAS NO: 2979-06-8
• Molecular Formula: C₁₁H₁₂O₃
• Molecular Weight: 192.21118
• Mol File: 2979-06-8.mol
• Article Data: 89

Chemical Properties

• Melting Point: 73～74℃
• Boiling Point: 320.2 °C at 760 mmHg
• Flash Point: 136.5 °C
• Appearance: /
• Density: 1.162 g/cm³
• Vapor Pressure: 0.000172mmHg at 25°C
• Refractive Index: 1.58
• CAS DataBase Reference: P-hydroxyl ethyl cinnaMate(CAS DataBase Reference)
• NIST Chemistry Reference: P-hydroxyl ethyl cinnaMate(2979-06-8)
• EPA Substance Registry System: P-hydroxyl ethyl cinnaMate(2979-06-8)

Safety Data

• Hazardous Substances Data: 2979-06-8(Hazardous Substances Data)

Usage

Chemical Properties

White or off-white solid powder

InChI:InChI=1/C11H12O3/c1-2-14-11(13)8-5-9-3-6-10(12)7-4-9/h3-8,12H,2H2,1H3/b8-5+

Upstream product

• 64-17-5 ethanol 
• 123-08-0 4-hydroxy-benzaldehyde 
• 105-36-2 ethyl bromoacetate 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 540-38-5 p-Iodophenol 
• 140-88-5 ethyl acrylate 
• 1071-46-1 hydrogen ethyl malonate 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 7400-08-0 p-Coumaric Acid 
• 144-55-8 sodium hydrogencarbonate 
• 25743-64-0 trans-p-acetoxycinnamic acid ethyl ester 
• 106-41-2 4-bromo-phenol 
• 227097-01-0 (E)-ethyl 3-(4-(allyloxy)phenyl)acrylate 
• 5048-82-8 ethyl 4-aminocinnamate 

Downstream Products

• 83021-94-7 ethyl p-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyloxy)cinnamate 
• 2979-06-8 cis-3-(4-Hydroxyphenyl)-2-propensaeure-ethylester 
• 244293-43-4 ethyl (E)-3-(4-(((tert-butyldimethylsilyl)oxy)phenyl)acrylate) 
• 440117-14-6 ethyl (E)-4-[2-(tert-butoxycarbonylamino)ethoxy]cinnamate 
• 440117-18-0 (E)-4-[2-(tert-butoxycarbonylamino)ethoxy]cinnamyl alcohol 
• 124607-18-7 5,7-dihydroxy-4-(4-hydroxyphenyl)-2H-1-benzopyran-2-one 
• 78589-65-8 3-(4-hydroxyphenyl)prop-2-yn-1-oic acid 
• 140-10-3 (E)-3-phenylacrylic acid 
• 928256-82-0 ethyl (E)-4-(3-chloropropoxy)cinnamate 
• 1018438-92-0 (E)-ethyl 3-(4-((3,5,6-trimethylpyrazin-2-yl)methoxy)phenyl)acrylate 
• 7400-08-0 para-coumaric acid 
• 27542-85-4 3-(4-acetoxyphenyl)acrylic acid 
• 10210-17-0 3-(4-hydroxyphenyl)propan-1-ol 
• 3690-05-9 4-hydroxycinnamic alcohol 

Relevant articles and documents

Preparation of Cinnamate Esters from Styrenes

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4'-O-beta-d-glucosyl-cis-p-coumaric acid - A natural constituent of Sphagnum fallax cultivated in bioreactors

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Prenylated trans-cinnamic esters and ethers against clinical fusarium spp.: Repositioning of natural compounds in antimicrobial discovery

Onychomycosis is a common nail infection mainly caused by species belonging to the F. oxysporum, F. solani, and F. fujikuroi species complexes. The aim of this study was to evaluate the in vitro susceptibility of six representative strains of clinically relevant Fusarium spp. toward a set of natural-occurring hydroxycinnamic acids and their derivatives with the purpose to develop naturally occurring products in order to cope with emerging resistance phenomena. By introducing a prenylated chain at one of the hydroxy groups of trans-cinnamic acids 1–3, ten prenylated derivatives (coded 4–13) were preliminarily investigated in solid Fusarium minimal medium (FMM). Minimal inhibitory concentration (MIC) and lethal dose 50 (LD50) values were then determined in liquid FMM for the most active selected antifungal p-coumaric acid 3,3′-dimethyl allyl ester 13, in comparison with the conventional fungicides terbinafine (TRB) and amphotericin B (AmB), through the quantification of the fungal growth. Significant growth inhibition was observed for prenylated derivatives 4–13, evidencing ester 13 as the most active. This compound presented MIC and LD50 values (62–250 μM and 7.8–125 μM, respectively) comparable to those determined for TRB and AmB in the majority of the tested pathogenic strains. The position and size of the prenylated chain and the presence of a free phenol OH group appear crucial for the antifungal activity. This work represents the first report on the activity of prenylated cinnamic esters and ethers against clinical Fusarium spp. and opens new avenues in the development of alternative antifungal compounds based on a drug repositioning strategy.

Hybrids of 4-hydroxy derivatives of goniothalamin and piplartine bearing a diester or a 1,2,3-triazole linker as antiproliferative agents

A library of nine hybrids of 4-hydroxygoniothalamin (2), 4-hydroxypiplartine (4), monastrol (5) and oxo-monastrol (6) was prepared via a modular synthetic route with a diester or a 1,2,3-triazole as linkers. The compounds were assayed against a panel of h