130734-47-3

Upstream product

• 331-39-5 caffeic acid 
• 100-51-6 benzyl alcohol 
• 2316-26-9 3,4-dimethoxycinnamic acid 
• 23416-69-5 caffeic acid chloride 
• 331-39-5 caffeic acid 
• 100-39-0 benzyl bromide 
• 77201-71-9 (E)-3-(3,4-dihydroxyphenyl)acryloyl chloride 
• 40204-26-0 malonic acid monobenzyl ester 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 621-59-0 isovanillin 
• 951288-55-4 (E)-benzyl 3-(3,4-bis(benzyloxy)phenyl)acrylate 
• 1338341-04-0 caffeic acid benzyl ester diacetate 
• 98631-72-2 3,4-diacetoxycinnamoyl chloride 
• 13788-48-2 di-O-acetylcaffeic acid 

Relevant academic research and scientific papers

Effect of 1-ethyl-3-methylimidazolium acetate on the oxidation of caffeic acid benzyl ester: An electrochemical and theoretical study

The effect of the ionic liquid (IL), 1-ethyl-3-methylimidazolium acetate ([emim][AcO]) on the oxidation of (E)-phenylmethyl-3-(3,4-dihydroxyphenyl)-2-propenoate (commonly known as caffeic acid benzyl ester [CABE]) was analyzed through experimental and theoretical methods, such as cyclic voltammetry (CV) and density functional theory (DFT) calculations. The obtained results demonstrated that the AcO? anion promotes the oxidation of the caffeic ester; this is because of the basic character of AcO?, which plays an important role to reduce the amount of energy required for the removal of one electron from the IL-CABE complex. This suggests that a strong hydrogen bond is formed between this anion and the phenolic H─O. Even the presence of water in the mixture of CABE-IL does not have a significant effect on the electrooxidation of the complex. Hence, it is possible to infer that CABE is more attached to [emim][AcO] than to the water molecules in the solvation sphere under the experimental conditions evaluated here. Other intermolecular interactions between CABE and IL also contribute to stabilize the resulting complex, e.g., van der Waals and cation-π interactions, which were evidenced through the theoretical noncovalent interactions (NCI) methodology. The relevant role of basic anions in the extraction of phenolic compounds, using ILs, has been documented in the literature; it should be considered that the strength of the hydrogen bond formed between the phenolic H─O and the IL should not contribute to the oxidation of target compounds.

Synthesis, DNA/RNA-interaction and biological activity of benzo[k,l]xanthene lignans

Interactions of two newly synthesized and six previously reported benzoxanthene lignans (BXLs), analogues of rare natural products, with DNA/RNA, G-quadruplex and HSA were evaluated by a set of spectrophotometric methods. Presence/absence of methoxy and hydroxy groups on the benzoxanthene core and minor modifications at C-1/C-2 side pendants – presence/absence of phenyl ring and presence/absence of methoxy and hydroxy groups on phenyl ring – influenced the fluorescence changes and the binding strength to double-stranded (ds-) and G-quadruplex structures. In general, compounds without phenyl ring showed stronger fluorescence changes upon binding than phenyl-substituted BXLs. On the other hand, BXLs with an unsubstituted phenyl ring showed the best stabilization effects of G-quadruplex. Circular dichroism spectroscopy results suggest mixed binding mode, groove binding and partial intercalation, to ds-DNA/RNA and end-stacking to top or bottom G-tetrads as the main binding modes of BXLs to those targets. All compounds exhibited micromolar binding affinities toward HSA and an increased protein thermal stability. Moderate to strong antiradical scavenging activity was observed for all BXLs with hydroxy groups at C-6, C-9 and C-10 positions of the benzoxanthene core, except for derivative bearing methoxy groups at these positions. BXLs with unsubstituted or low-substituted phenyl ring and one derivative without phenyl ring showed strong growth inhibition of Gram-positive Staphylococcus aureus. All compounds showed moderate to strong tumor cell growth-inhibitory activity and cytotoxicity.

Bioinspired benzoxanthene lignans as a new class of antimycotic agents: synthesis and Candida spp. growth inhibition

In this work we synthetized the bioinspired benzoxanthene lignans (BXLs) 3, 14–22, and the phenazine derivative 23 as potential antimycotic agents. MICs and MFCs against Candida strains were determined. In a preliminary screening, compounds 3, 15, 20, 21,

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.

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.

Synthesis, Antibacterial Evaluation, and QSAR of Caffeic Acid Derivatives

The present study evaluates the antibacterial effects of a set of 16 synthesized caffeic acid ester derivatives against strains of Staphylococcus aureus and Escherichia coli, as well as discusses their structure-activity relationship (SAR). The antibacterial assays were performed using microdilution techniques in 96-well microplates to determine minimal inhibitory concentration (MIC). The results revealed that five of the compounds present strong to optimum antibacterial effect. Of the sixteen ester derivatives evaluated, the products with alkyl side chains, as propyl caffeate (3), butyl caffeate (6), and pentyl caffeate (7), presented the best antibacterial activity with MIC values of around 0.20 μM against Escherichia coli and only butyl caffeate (6) showing the same MIC against Staphylococcus aureus. For products with aryl substituents, the best MIC results against the tested strain of Escherichia coli were 0.23 μM for (di-(4-chlorobenzyl)) caffeate (13) and 0.29 μM for diphenylmethyl caffeate (10) and all were less active against the Staphylococcus aureus strain. Preliminary quantitative structure-activity relationship (QSAR) analyses confirmed that certain structural characteristics, such as a median linear carbon chain and the presence of electron withdrawal substituents at the para position of the aromatic ring, help potentiate antibacterial activity.

A method for preparing coffee acid benzyl ester

The invention discloses a coffee acid benzyl ester of preparation method, the overall steps are: a, the caffeic acid dissolved in organic solvent, the reaction is carried out by adding thionyl chloride, make intermediate A; b, alkali and the presence of o

Caffeic acid esters are effective bactericidal compounds against paenibacillus larvae by altering intracellular oxidant and antioxidant levels

American Foulbrood (AFB) is a deadly bacterial disease affecting pupal and larval honey bees. AFB is caused by the endospore-forming bacterium Paenibacillus larvae (PL). Propolis, which contains a variety of organic compounds, is a product of bee foraging and is a resinous substance derived from botanical substances found primarily in trees. Several compounds from the class of caffeic acid esters, which are commonly found in propolis, have been shown to have antibacterial activity against PL. In this study, six different caffeic acid esters were synthesized, purified, spectroscopically analyzed, and tested for their activity against PL to determine the minimum inhibitory concentrations (MICs) and minimum bactericidal concentrations (MBCs). Caffeic acid isopropenyl ester (CAIE), caffeic acid benzyl ester (CABE), and caffeic acid phenethyl ester (CAPE) were the most effective in inhibiting PL growth and killing PL cell with MICs and MBCs of 125 μg/mL when used individually, and a MIC and MBC of 31.25 μg/mL for each compound alone when CAIE, CABE, and CAPE are used in combination against PL. These compounds inhibited bacterial growth through a bactericidal effect, which revealed cell killing but no lysis of PL cells after 18 h. Incubation with CAIE, CABE, and CAPE at their MICs significantly increased reactive oxygen species levels and significantly changed glutathione levels within PL cells. Caffeic acid esters are potent bactericidal compounds against PL and eliminate bacterial growth through an oxidative stress mechanism.

Synthesis and activity towards Alzheimer's disease in vitro: Tacrine, phenolic acid and ligustrazine hybrids

A series of novel tacrine-phenolic acid dihybrids and tacrine-phenolic acid-ligustrazine trihybrids were synthesized, characterized and screened as novel potential anti-Alzheimer drug candidates. These compounds showed potent inhibition activity towards cholinesterases (ChEs), among of them, 9i was the most potent one towards acetylcholinesterase (eeAChE, IC50 = 3.9 nM; hAChE, IC50 = 65.2 nM). 9i could also effectively block β-amyloid (Aβ) self-aggregation with an inhibition ratio of 47% at 20 μM. In addition, its strong anti-oxidation activity could protect PC12 cells from CoCl2-damage in the experimental condition while no neurotoxicity. Furthermore, its hepatotoxicity was lower than tacrine in vitro and in vivo. Kinetic and molecular modeling studies revealed that 9i worked in a mixed-type way, could interact simultaneously with catalytic active site (CAS) and peripheral anionic site (PAS) of AChE. Therefore, 9i was a promising multifunctional candidate for the treatment of AD.

Protective effect of caffeic acid derivatives on tert-butyl hydroperoxide-induced oxidative hepato-toxicity and mitochondrial dysfunction in HepG2 cells

Oxidative stress results in structural and functional abnormalities in the liver and is thought to be a crucial factor in liver diseases. The aim of this study was to investigate the cytoprotective and antioxidant effects of caffeic acid (CA) derivatives