1166-52-5Relevant articles and documents
Inhibitory effect of gallic acid and its esters on 2,2'-azobis(2- amidinopropane)hydrochloride (AAPH)-induced hemolysis and depletion of intracellular glutathione in erythrocytes
Ximenes, Valdecir F.,Lopes, Mariana G.,Petronio, Maicon Segalla,Regasini, Luis Octavio,Siqueira Silva, Dulce H.,Da Fonseca, Luiz M.
, p. 5355 - 5362 (2010)
The protective effect of gallic acid and its esters, methyl, propyl, and lauryl gallate, against 2,2'-azobis(2-amidinopropane)hydrochloride (AAPH)-induced hemolysis and depletion of intracellular glutathione (GSH) in erythrocytes was studied. The inhibition of hemolysis was dose-dependent, and the esters were significantly more effective than gallic acid. Gallic acid and its esters were compared with regard to their reactivity to free radicals, using the DPPH and AAPH/pyranine free-cell assays, and no significant difference was obtained. Gallic acid and its esters not only failed to inhibit the depletion of intracellular GSH in erythrocytes induced by AAPH but exacerbated it. Similarly, the oxidation of GSH by AAPH or horseradish peroxidase/H 2O2 in cell-free systems was exacerbated by gallic acid or gallates. This property could be involved in the recent findings on pro-apoptotic and pro-oxidant activities of gallates in tumor cells. We provide evidence that lipophilicity and not only radical scavenger potency is an important factor regarding the efficiency of antihemolytic substances.
Synthetic method of dodecyl gallate
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Paragraph 0022-0025, (2020/06/17)
The invention relates to a synthesis method of dodecanoyl gallate. The synthesis method comprises the following steps: 1) carrying out a primary reaction to obtain a dodecanoyl gallate crude product and an applied mother liquor; 2) applying the mother liquor to obtain a dodecanoyl gallate crude product; and 3) preparing a dodecanoyl gallate refined product by combining the crude product. The preparation method mainly comprises the following steps: carrying out a primary reaction on anhydrous gallic acid and a dodecanol to obtain a crude product and a mother liquor, carrying out an applying reaction on anhydrous gallic acid, dodecanol and the mother liquor to obtain a dodecanoyl gallate crude product, and finally preparing the refined product from the crude products obtained by the two reactions. The reaction synthesis method is simple, the raw material utilization rate is high, the product purity can reach more than 99%, and the product yield can reach more than 75%.
Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors
Rivero-Buceta, Eva,Carrero, Paula,Doyagüez, Elisa G.,Madrona, Andrés,Quesada, Ernesto,Camarasa, María José,Peréz-Pérez, María Jesús,Leyssen, Pieter,Paeshuyse, Jan,Balzarini, Jan,Neyts, Johan,San-Félix, Ana
, p. 656 - 671 (2015/01/30)
Linear and branched compounds that contain two, three or five units of galloyl (3,4,5-trihydroxybenzoyl) or its isomer 2,3,4-trihydroxybenzoyl, as well as other mono- or dihydroxybenzoyl moieties have been synthesized. These molecules have been evaluated for their in vitro inhibitory effects against a wide panel of viruses showing preferential activity against HIV and HCV. Our structure-activity relationship studies demonstrated that the 2,3,4-trihydroxybenzoyl moiety provides better antiviral activities than the galloyl (3,4,5-trihydroxybenzoyl) moiety that is present in natural green tea catechins. This observation can be of interest for the further rational exploration of compounds with anti-HCV/HIV properties. The most notable finding with respect to HIV is that the tripodal compounds 43 and 45, with three 2,3,4-trihydroxybenzoyl moieties, showed higher activities than linear compounds with only one or two. With respect to HCV, the linear compounds, 52 and 41, containing a 12 polymethylene chain and two 2,3 di- or 2,3,4 tri-hydroxybenzoyl groups respectively at the ends of the molecule showed good antiviral efficiency. Furthermore, the anti-HCV activity of both compounds was observed at concentrations well below the cytotoxicity threshold. A representative member of these compounds, 41, showed that the anti-HCV activity was largely independent of the genetic make-up of the HCV subgenomic replicon and cell lines used.