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• 99-50-3 3,4-Dihydroxybenzoic acid 
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Relevant academic research and scientific papers

Protocatechuic acid alkyl esters: Hydrophobicity as a determinant factor for inhibition of NADPH oxidase

This study presents the increased efficiency of NADPH oxidase inhibition produced by esterification of protocatechuic acid (P0). Alkyl esters bearing chain lengths of 4 (P4), 7 (P7) and 10 (P10) carbons were synthesized and their oxidation potential, hydr

Improvement of pro-oxidant capacity of protocatechuic acid by esterification

Pro-oxidant effects of phenolic compounds are usually correlated to the one-electron redox potential of the phenoxyl radicals. Here we demonstrated that, besides their oxidizability, hydrophobicity can also be a decisive factor. We found that esterificati

Synthesis and application of acrylic resin based on protocatechuic acid

The invention discloses synthesis and application of acrylic resin based on protocatechuic acid. According to the method, protocatechuic acid is used as a raw material, firstly, alcohol is used for esterification, and then the raw material and acryloyl chloride are synthesized into the protocatechuic acid-based acrylic resin monomer (M) through a one-pot method. And the acrylic resin based on protocatechuic acid is used for modifying polymethyl methacrylate (organic glass). The resin monomer is copolymerized with methyl methacrylate (MMA), the glass transition temperature (Tg) is increased along with the increase of the M content, and when the M content is 50%, the Tg of the copolymer is 159.6 DEG C (the heat resistance is improved by 51 DEG C). The Td5 of the copolymer is 358 DEG C (increased by 48 DEG C), and the residual carbon rate is 12.57%. In addition, the copolymerization product also shows the characteristic of absorbing short-wave blue light. The synthesis method provided by the invention is mild in reaction condition and relatively high in yield, and has a relatively great application prospect in the application field of optical electronics. The invention also widens the application range of biological resources.

Metabolite profile of Nectandra oppositifolia Nees & Mart. And assessment of antitrypanosomal activity of bioactive compounds through efficiency analyses

EtOH extracts from the leaves and twigs of Nectandra oppositifolia Nees & Mart. shown activity against amastigote forms of Trypanosoma cruzi. These extracts were subjected to successive liquid-liquid partitioning to afford bioactive CH2Cl2 fractions. UHPL

Design of antibacterial agents: Alkyl dihydroxybenzoates against xanthomonas citri subsp. citri

Xanthomonas citri subsp. citri (Xcc) causes citrus canker, affecting sweet orange-producing areas around the world. The current chemical treatment available for this disease is based on cupric compounds. For this reason, the objective of this study was to design antibacterial agents. In order to do this, we analyzed the anti-Xcc activity of 36 alkyl dihydroxybenzoates and we found 14 active compounds. Among them, three esters with the lowest minimum inhibitory concentration values were selected; compounds 4 (52 μM), 16 (80 μM) and 28 (88 μM). Our study demonstrated that alkyl dihydroxybenzoates cause a delay in the exponential phase. The permeability capacity of alkyl dihydroxybenzoates in a quarter of MIC was compared to nisin (positive control). Compound 28 was the most effective (93.8), compared to compound 16 (41.3) and compound 4 (13.9) by percentage values. Finally, all three compounds showed inhibition of FtsZ GTPase activity, and promoted changes in protofilaments, leading to depolymerization, which prevents bacterial cell division. In conclusion, heptyl dihydroxybenzoates (compounds 4, 16 and 28) are promising anti-Xcc agents which may serve as an alternative for the control of citrus canker.

Antioxidant activity of protocatechuates evaluated by DPPH, ORAC, and CAT methods

Hibiscus sabdariffa L. is a worldwide consumed plant, principally after infusion of its dried sepals and calyces, which are usually discarded. Nevertheless, they represent a potential source of natural bioactive compounds, e.g. polyphenols, which could ad

Alkyl hydroxybenzoic acid derivatives that inhibit HIV-1 protease dimerization

The therapeutic potential of gallic acid and its derivatives as anti-cancer, antimicrobial and antiviral agents is well known. We have examined the mechanism by which natural gallic acid and newly synthesized gallic acid alkyl esters and related protocatechuic acid alkyl esters inhibit HIV-1 protease to compare the influence of the aromatic ring substitutions on inhibition. We used Zhang-Poorman's kinetic analysis and fluorescent probe binding to demonstrate that several gallic and protecatechuic acid alkyl esters inhibited HIV-1 protease by preventing the dimerization of this obligate homodimeric aspartic protease rather than targeting the active site. The tri-hydroxy substituted benzoic moiety in gallates was more favorable than the di-substituted one in protocatechuates. In both series, the type of inhibition, its mechanism and the inhibitory efficiency dramatically depended on the length of the alkyl chain: no inhibition with alkyl chains less than 8 carbon atoms long. Molecular dynamics simulations corroborated the kinetic data and propose that gallic esters are intercalated between the two N- and C-monomer ends. They complete the β-sheet and disrupt the dimeric enzyme. The best gallic ester (14 carbon atoms, Kid of 320 nM) also inhibited the multi-mutated protease MDR-HM. These results will aid the rational design of future generations of non-peptide inhibitors of HIV-1 protease dimerization that inhibit multi-mutated proteases. Finally, our work suggests the wide use of gallic and protocatechuic alkyl esters to dissociate intermolecular β-sheets involved in protein-protein interactions.

Molecular design of multifunctional food additives: Antioxidative antifungal agents

A series of alkyl 3,4-dihydroxybenzoates (protocatechuates) was synthesized, and their fungicidal activity against Saccharomyces cerevisiae was assayed using a 2-fold serial broth dilution method. Nonyl and octyl 3,4-dihydroxybenzoate were noted to be the most effective against this yeast with the minimum fungicidal concentration of 12.5 μg/mL each. The activity was found to correlate with the hydrophobic alkyl chain length. The time-kill curve study showed that nonyl 3,4-dihydroxybenzoate was fungicidal against S. cerevisiae at any growth stage and this activity was not influenced by pH values. The fungicidal activity of alkyl 3,4-dihydroxybenzoates was noted in combination with their ability to disrupt the native membrane-associated function nonspecifically as surface-active agents (surfactants) and to inhibit the respiratory electron transport. However, the primary fungicidal activity of nonyl 3,4-dihydroxybenzoate likely comes from its ability to act as a surfactant.