115610-29-2

Usage

Uses

Used in Cancer Therapy:
CAPE is used as an anti-cancer agent for its ability to inhibit the growth of cancer cells. It has been studied for its potential to target various types of cancer and may be used in combination with conventional treatments to enhance their efficacy.
Used in Anti-Inflammatory Applications:
In conditions such as arthritis, CAPE is used as an anti-inflammatory agent to reduce inflammation and alleviate pain. Its anti-inflammatory properties make it a potential candidate for the treatment of various inflammatory disorders.
Used in Antioxidant Therapy:
CAPE is used as an antioxidant to protect against oxidative stress and reduce the damage caused by free radicals. Its antioxidant properties may help in preventing or treating various diseases associated with oxidative stress, such as neurodegenerative disorders.
Used in Cognitive Function Improvement:
CAPE is used as a cognitive enhancer to improve cognitive function and protect against neurodegenerative diseases. Its potential neuroprotective effects make it a promising candidate for the prevention and treatment of cognitive decline and related disorders.
Overall, CAPE shows promise as a natural compound with potential health benefits across various applications. Further research is needed to fully understand its mechanisms and explore its potential applications in different industries.

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

Relevant academic research and scientific papers

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.

Catechol-based inhibitors of bacterial urease

Targeted covalent inhibitors of urease were developed on the basis of the catechol structure. Forty amide and ester derivatives of 3,4-dihydroxyphenylacetic acid, caffeic acid, ferulic acid and gallic acid were obtained and screened against Sporosarcinia pasteurii urease. The most active compound, namely propargyl ester of 3,4-dihydroxyphenylacetic acid exhibited IC50 = 518 nM andkinact/Ki = 1379 M?1 s?1. Inhibitory activity of this compound was better and toxicity lower than those obtained for the starting compound – catechol. The molecular modelling studies revealed a mode of binding consistent with structure-activity relationships.

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 of Diverse Hydroxycinnamoyl Phenylethanoid Esters Using Escherichia coli

Caffeic acid phenethyl ester (CAPE) is an ester of a hydroxycinnamic acid (phenylpropanoid) and a phenylethanoid (2-phenylethanol; 2-PE), which has long been used in traditional medicine. Here, we synthesized 54 hydroxycinnamic acid-phenylethanoid esters by feeding 64 combinations of hydroxycinnamic acids and phenylethanols to Escherichia coli harboring the rice genes OsPMT and Os4CL. The same approach was applied for ester synthesis with caffeic acid and eight different phenyl alcohols. Two hydroxycinnamoyl phenethyl esters, p-coumaroyl tyrosol and CAPE, were also synthesized from glucose using engineered E. coli by introducing genes for the synthesis of substrates. Consequently, we synthesized approximately 393.4 mg/L p-coumaroyl tyrosol and 23.8 mg/L CAPE with this approach. Overall, these findings demonstrate that the rice PMT and 4CL proteins can be used for the synthesis of diverse hydroxycinnamoyl phenylethanoid esters owing to their promiscuity and that further exploration of the biological activities of these compounds is warranted.

Crystal form II of caffeic acid phenethyl ester, and preparation method and use thereof

The invention provides a crystal form II of caffeic acid phenethyl ester, and a preparation method and a use thereof. The caffeic acid phenethyl ester has a structure represented by formula I, and diffraction peaks represented by 2theta diffraction angles of 6.199 DEG, 18.439 DEG, 22.560 DEG, 26.481 DEG and 30.721 DEG exist in an X-ray powder diffraction map of the crystal form II radiated with CuKalpha. The novel crystal form has a better stability than other forms. The preparation method of the novel crystal form has the characteristics of simple process, high yield and good stability.

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).

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.

Development of blood-brain barrier permeable nitrocatechol-based catechol O-methyltransferase inhibitors with reduced potential for hepatotoxicity

Recent efforts have been focused on the development of centrally active COMT inhibitors, which can be valuable assets for neurological disorders such as Parkinson's disease, due to the severe hepatotoxicity risk associated with tolcapone. New nitrocatechol COMT inhibitors based on naturally occurring caffeic acid and caffeic acid phenethyl ester were developed. All nitrocatechol derivatives displayed potent inhibition of peripheral and cerebral COMT within the nanomolar range. Druglike derivatives 13, 15, and 16 were predicted to cross the blood-brain barrier in vitro and were significantly less toxic than tolcapone and entacapone when incubated at 50 μM with rat primary hepatocytes. Moreover, their unique acidity and electrochemical properties decreased the chances of formation of reactive quinone-imines and, as such, the potential for hepatotoxicity. The binding mode of 16 confirmed that the major interactions with COMT were established via the nitrocatechol ring, allowing derivatization of the side chain for future lead optimization efforts.

Synthesis and antitumor activity of feruloyl and caffeoyl derivatives This paper is dedicated to Prof. Wei-xiao Hu for his lifelong commitment to mentoring graduate students

We developed two efficient protocols for the synthesis of feruloyl and caffeoyl derivatives from commercial vanillin and veratraldehyde. Pharmacological activities were assessed against a panel of human cancer cell lines in vitro. Most synthesized compounds demonstrated attractive cytotoxicity. Several new compounds demonstrated significant antiproliferative and cytotoxic activities against HeLa and Bewo tumor cell lines. In particular, 5-nitro caffeic adamantyl ester showed broad spectrum of tumor inhibition in 10 cell lines, and reduced tumor weight by 36.7% in vivo when administered at a dose of 40 mg kg-1.

A rapid and practical catalytic esterification for the preparation of caffeic acid esters

A convenient and practical catalytic method for the preparation of caffeic acid esters is reported. This esterification was carried out with high efficiency in the presence of ytterbium triflate in nitromethane without any other auxiliary reagents. The wide scope of application and especially the higher reactivity and more convenient procedure than previous methods make it a valuable application for the synthesis of caffeic acid esters and other cinnamic acid esters.