100668-06-2

Upstream product

• 71-41-0 pentan-1-ol 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 331-39-5 caffeic acid 

Relevant academic research and scientific papers

Structure–activity relations of rosmarinic acid derivatives for the amyloid β aggregation inhibition and antioxidant properties

Amyloid-β aggregation inhibitors are expected to be therapeutic or prophylactic agents for Alzheimer's disease. Rosmarinic acid, which is one of the main aggregation inhibitors derived from Lamiaceae, was employed as a lead compound and its 25 derivatives were synthesized. In this study, the structure–activity relations of rosmarinic acid derivatives for the amyloid-β aggregation inhibitory effect (MSHTS assay), antioxidant properties, and xanthine oxidase inhibition were evaluated. Among the tested compounds, compounds 16d and 19 were found to the most potent amyloid aggregation inhibitors. The SAR revealed that the necessity of the presence of the phenolic hydroxyl on one side of the molecule as well as the lipophilicity of the entire molecule. The importance of these structural properties was also supported by docking simulations.

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.

Optimizing the efficiency of antioxidants in emulsions by lipophilization: Tuning interfacial concentrations

Optimization of the efficiency of antioxidants, AOs, in lipid-based emulsions via chemical modifications of their reactive moieties is not always possible because of the inherent experimental difficulties and because of the regulatory status of AOs. Esterification of hydrophilic AOs may be a practical, convenient, alternative approach. Here we employed a series of caffeic acid derivatives bearing the same reactive moiety but of different hydrophobicity (alkyl chain lengths of 1 to 16 carbon atoms) to investigate the effects of hydrophobicity on the oxidative stability of stripped corn oil-in-water emulsions. AO efficiency was determined by monitoring the production of primary oxidation products (conjugated dienes) with time and a non-linear, parabolic-like, variation of their efficiency with the number of C atoms in their alkyl chain, with a maximum at the C8 derivative, found. To rationalize the results, we also determined the distribution of the AOs between the oil, interfacial and aqueous regions of the same emulsions by employing a recently developed kinetic method that provides the partition constants of the AO between the oil-interfacial, PIO, and water-interfacial, PIW, regions of the intact emulsions. Values of both PIO and PIW range between 180-2000, suggesting that the transfer of the AOs to the interfacial region is spontaneous. The results indicate that the variations of both the percentage of AO in the interfacial region, % AOI, of the emulsions and the AO efficiency with the number of C atoms in the AO alkyl chain parallel each other with a maxima at the C8 derivative. The results illustrate an effective and convenient way to control lipid oxidation by modulation of the hydrophobicity (HLB) of the AOs. An increase in the alkyl chain length of the AOs promote their incorporation into the interfacial region of emulsions but only up to a critical chain length, after which a further increase makes their efficiency decrease as a consequence of the decrease in their % AOI.

Biological activity evaluation and structure-activity relationships analysis of ferulic acid and caffeic acid derivatives for anticancer

The anticancer activities of alkyl esters and NO-donors of ferulic acid (FA) and caffeic acid (CA) were assessed by a high-throughout screening (HTS) method, and the structure-activity relationships were described. CA alkyl esters had better anticancer activities than FA alkyl esters with the same alkyl substituent. Mono-nitrates and phenylfuroxan nitrates were more potent than the dual nitrates. Phenylsulfonylfuroxan nitrates of FA, especially compounds 8b-8d, exhibited more potent activities in anticancer.