3856-05-1

Usage

Uses

Used in Food Industry:
Isobutyl gallate is used as a preservative and antioxidant for extending the shelf life of food products. It prevents the oxidation of fats and oils, thereby maintaining the freshness and quality of the food items.
Used in Cosmetics Industry:
Isobutyl gallate is used as an antioxidant in cosmetics to prevent the degradation of active ingredients and to extend the product's shelf life. It helps maintain the stability and efficacy of cosmetic formulations.
Used in Pharmaceutical Industry:
Isobutyl gallate is used as a stabilizer in pharmaceutical formulations to prevent the oxidation of sensitive compounds, ensuring the stability and potency of the drugs.
Used in Plastic Industry:
Isobutyl gallate is used as a stabilizer in plastic products to prevent the degradation of polymers, thereby enhancing the durability and longevity of the plastic materials.
Used in Industrial Processes:
Isobutyl gallate is used as a component in some industrial processes to prevent oxidation and spoilage, ensuring the stability and quality of the end products.
However, it is important to note that there are concerns about the potential health effects and environmental impact of isobutyl gallate. As a result, its use and application are regulated in certain jurisdictions to ensure safety and sustainability.

InChI:InChI=1/C11H14O5/c1-6(2)5-16-11(15)7-3-8(12)10(14)9(13)4-7/h3-4,6,12-14H,5H2,1-2H3

Upstream product

• 78-83-1 2-methyl-propan-1-ol 
• 149-91-7 3,4,5-trihydroxybenzoic acid 

Relevant academic research and scientific papers

Design, Synthesis, and Antifungal Activity of Alkyl Gallates Against Plant Pathogenic Fungi In Vitro and In Vivo

A series of alkyl gallates was synthesized by reacting gallic acid with the corresponding alcohols. Their structures were determined on the basis of spectroscopic data, including NMR and MS. The antifungal activities of these compounds against plant pathogenic fungi in vitro and in vivo were assessed.

Synthesis and in vitro antimalarial activity of alkyl esters of gallate as a growth inhibitor of plasmodium falciparum

This study is aimed to synthesize alkyl esters gallate and determine its in vitro antimalarial activity against parasite Plasmodium falciparum. Fourteen compounds of alkyl esters gallate were synthesized by esterification of the carboxyl group of gallic acid with a series of alkyl alcohols, as well as methoxylation of the hydroxy groups on the aromatic ring of gallic acid. Antimalarial activity of the synthesized alkyl esters gallate were expressed by IC50 value, with gallic acid as an original compound and artemisin as a positive control. Compared to gallic acid, eleven synthesized compounds of alkyl esters gallate, have a greater antimalarial activity against Plasmodium falciparum. On the other hand, three compounds, that are propyl gallate, butyl gallate and trimethoxy methyl gallate, showed a lower antimalarial activity. Moreover, compared to gallic acid (IC50: 194.86 mM) and artemisin (IC50: 0.5 mM), two synthesized compounds of alkyl gallates, namely methyl gallate and hexyl gallate exhibited the stronger antimalarial activity against Plasmodium falciparum, with IC50 value of 0.03 mM and 0.11 mM, respectively. Our result clearly demonstrated that methyl gallate and hexyl gallate as a promising candidate for the new antimalarial agents.

Synthetic method of gallic acid lower alkanol ester

A synthetic method of gallic acid lower alkanol ester comprises the following steps of: (1) placing gallic acid and lower alkanol in a reactor, adding a sulfonic acid resin catalyst subjected to hydrophobic modification, carrying out stirring, heating to a temperature of 65 to 120 DEG C, performing the reaction for 4 to 10h and filtering to obtain filtrate; (2) removing excessive alcohol in the filtrate by evaporation so as to obtain a crude product, then carrying out recrystallization by deionized water, and carrying out suction filtration and drying to obtain the gallic acid lower alkanol ester. The synthetic method disclosed by the invention is simple, is safe to operate; yield of the gallic acid lower alkanol ester is greater than or equal to 92 percent; product purity is more than or equal to 99.5 percent; moreover, the catalyst has excellent performance; the water distribution link in a conventional method is reduced; a reaction apparatus is simplified; the synthetic method has good repeatability.

Microwave-assisted esterification of gallic acid

An efficient synthesis of alkyl gallates under microwave irradiation was described. The reaction took place in 6-10 mins, which was much shorter than the traditional synthetic methods, with almost quantitative yields.

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.

Suppression of TNF-α induced NFκB activity by gallic acid and its semi-synthetic esters: Possible role in cancer chemoprevention

Gallic acid (3,4,5-trihydroxybenzoic acid), found in many plants either in free-form or part of tannins, is known to possess anti-microbial, antioxidant and cytotoxic properties. NFκB regulates the expression of several genes involved in carcinogenesis. These include anti-apoptotic, cytokines and cell cycle-regulatory genes. It is well established that the transcriptional factor NFκB is deregulated in many forms of cancer. Thus, agents that can suppress NFκB activation have the potential of suppressing carcinogenesis. In the present investigation, gallic acid was isolated from Alchornea glandulosa (Euphorbiaceae) and eight esters were synthesised. These compounds were evaluated against TNF-α-induced NFκB activation with stably transfected 293/NFκB-Luc human embryonic kidney cells. Gallates with IC50 values in a range of 10-56 M mediated inhibitory activity higher than gallic acid (IC50 76.0 4.9 M). In addition to inhibiting NFκB activation, gallic acid mediated a modest cytotoxic effect, and some of the gallates affected cell viability at the tested concentrations. Based on these results, suppression of NFκB activation by gallate esters could play a chemopreventive role in carcinogenesis.