115610-29-2

Basic information

• Product Name: CAPE
• Synonyms: PHENETHYL CAFFEIATE;PHENETHYL 3,4-DIHYDROXYCINNAMATE;PHENYLETHYL CAFFEATE;CAPE;CAFFEIC ACID PHENYLETHYL ESTER;(E)-3-(3,4-DIHYDROXYPHENYL)-2-PROPENOIC ACID, 2-PHENYLETHYL ESTER;(E)-3-(3,4-Dihydroxyphenyl)propenoic acid phenethyl ester;(βE)-3,4-Dihydroxybenzeneacrylic acid phenethyl ester
• CAS NO: 115610-29-2
• Molecular Formula: C₁₇H₁₆O₄
• Molecular Weight: 284.31
• Mol File: 115610-29-2.mol
• Article Data: 22

Chemical Properties

• Melting Point: 121-123 °C
• Boiling Point: 498.6 °C at 760 mmHg
• Flash Point: 185.1 °C
• Appearance: /
• Density: 1.266 /cm³
• Vapor Pressure: 1.45E-10mmHg at 25°C
• Refractive Index: 1.645
• Storage Temp.: -20°C
• PKA: 9.32±0.10(Predicted)
• CAS DataBase Reference: CAPE(CAS DataBase Reference)
• NIST Chemistry Reference: CAPE(115610-29-2)
• EPA Substance Registry System: CAPE(115610-29-2)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:
• Safety Statements: S26:; S36:
• Hazardous Substances Data: 115610-29-2(Hazardous Substances Data)

Usage

General Description

Caffeic acid phenethyl ester (CAPE) is a natural substance found in propolis, a resinous substance collected by honeybees from various plants. It has been shown to have anti-inflammatory, antioxidant, and anti-cancer properties, making it a potential therapeutic agent for a variety of health conditions. CAPE has been studied for its ability to inhibit the growth of cancer cells, reduce inflammation in conditions such as arthritis, and protect against oxidative stress. It has also been examined for its potential to improve cognitive function and protect against neurodegenerative diseases. Overall, CAPE shows promise as a natural compound with potential health benefits, and further research is needed to fully understand its mechanisms and potential applications.

InChI:InChI=1/C17H16O4/c18-15-8-6-14(12-16(15)19)7-9-17(20)21-11-10-13-4-2-1-3-5-13/h1-9,12,18-19H,10-11H2/b9-7+

Upstream product

• 60-12-8 2-phenylethanol 
• 77201-71-9 (E)-3-(3,4-dihydroxyphenyl)acryloyl chloride 
• 103-82-2 phenylacetic acid 
• 621-59-0 isovanillin 
• 88623-81-8 3,4-diacetoxycinnamic acid 
• 118971-54-3 (E)-4-(3-oxo-3-phenethoxyprop-1-enyl)-1,2-phenylene diacetate 
• 331-39-5 caffeic acid 
• 92778-42-2 malonic acid di(2-phenylethyl) ester 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 848598-50-5 malonic acid monophenethyl ester 
• 103-63-9 1-phenyl-2-bromoethane 
• 538-75-0 dicyclohexyl-carbodiimide 

Relevant articles and documents

Caffeic acid phenethyl ester (CAPE)-derivatives act as selective inhibitors of acetylcholinesterase

Unexpected inhibitory effects against eeAChE could be found for a newly synthesized class of caffeic acid phenethyl ester (CAPE)derivatives. Thus, phenethyl-(E)-3-(3,5-dimethoxy-4-phenethoxyphenyl)-acrylate (Ki = 1.97 ± 0.38 μM, Ki′ = 2.44 ± 0.07 μM)and 4-(2-(((E)-3-(3,4-bis(benzyloxy)phenyl)acryloyl)oxy)ethyl)-1,2-phenylene (2E,2′E)-bis(3-(3,4-bis(benzyloxy)phenyl)acrylate)(Ki = 0.72 ± 0.31 μM, Ki′ = 1.80 ± 0.21 μM)showed very good inhibition of eeAChE, while being non cytotoxic for malignant human cancer cells and non-malignant mouse fibroblasts. Also, they are weak inhibitors for BChE (from equine serum).

Synthesis and characterization of CAPE derivatives as xanthine oxidase inhibitors with radical scavenging properties

Inhibitors of the enzyme xanthine oxidase (XO) with radical scavenging properties hold promise as novel agents against reperfusion injuries after ischemic events. By suppressing the formation of damaging reactive oxygen species (ROS) by XO or scavenging ROS from other sources, these compounds may prevent a buildup of ROS in the aftermath of a heart attack or stroke. To combine these two properties in a single molecule, we synthesized and characterized the non-purine XO inhibitor caffeic acid phenethylester (CAPE) and 19 derivatives using a convenient microwave-assisted Knoevenagel condensation protocol. Varying systematically the number and positions of the hydroxyl groups at the two phenyl rings, we derived structure-activity relationships based on experimentally determined XO inhibition data. Molecular docking suggested that critical enzyme/inhibitor interactions involved π-π interactions between the phenolic inhibitor ring and Tyr914, hydrogen bonds between inhibitor hydroxyl groups and Glu802, and hydrophobic interactions between the CAPE phenyl ring and non-polar residues located at the entrance of the binding site. To effectively scavenge the stable radical DPPH, two hydroxyl groups in 1,2- or 1,4-position at the phenyl ring were required. Among all compounds tested, E-phenyl 3-(3,4-dihydroxyphenyl)acrylate, a CAPE analog without the ethyl tether, showed the most promising properties.

Antiproliferative activity and SARs of caffeic acid esters with mono-substituted phenylethanols moiety

A series of CAPE derivatives with mono-substituted phenylethanols moiety were synthesized and evaluated by MTT assay on growth of 4 human cancer cell lines (Hela, DU-145, MCF-7 and ECA-109). The substituent effects on the antiproliferative activity were systematically investigated for the first time. It was found that electron-donating and hydrophobic substituents at 2′-position of phenylethanol moiety could significantly enhance CAPE's antiproliferative activity. 2′-Propoxyl derivative, as a novel caffeic acid ester, exhibited exquisite potency (IC50?=?0.4?±?0.02 & 0.6?±?0.03?μM against Hela and DU-145 respectively).