3856-05-1

Basic information

• Product Name: ISOBUTYL GALLATE
• Synonyms: GALLIC ACID ISO-BUTYL ESTER;ISOBUTYL GALLATE;isobutyl 3,4,5-trihydroxybenzoate;3,4,5-Trihydroxybenzoic acid 2-methylpropyl ester;3,4,5-Trihydroxybenzoic acid isobutyl ester;2-methylpropyl 3,4,5-trihydroxybenzoate
• CAS NO: 3856-05-1
• Molecular Formula: C₁₁H₁₄O₅
• Molecular Weight: 226.23
• EINECS: 223-363-9
• Product Categories: Aromatic Esters
• Mol File: 3856-05-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 142 °C
• Boiling Point: 444.3°Cat760mmHg
• Flash Point: 175.4°C
• Appearance: /
• Density: 1.311g/cm³
• Vapor Pressure: 1.65E-08mmHg at 25°C
• Refractive Index: 1.581
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 7.89±0.25(Predicted)
• CAS DataBase Reference: ISOBUTYL GALLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ISOBUTYL GALLATE(3856-05-1)
• EPA Substance Registry System: ISOBUTYL GALLATE(3856-05-1)

Safety Data

• Hazardous Substances Data: 3856-05-1(Hazardous Substances Data)

Usage

General Description

Isobutyl gallate is a synthetic chemical compound that is frequently used as an antioxidant in food, cosmetics, and pharmaceuticals. It is produced by combining gallic acid with isobutanol, resulting in a substance that helps to prevent oxidation and spoilage in products. Isobutyl gallate is also used as a stabilizer in plastic products and as a component in some industrial processes. However, there is some concern about its potential health effects and its impact on the environment, so its use and application are regulated in certain jurisdictions.

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 articles and documents

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.

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.

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.