19198-75-5

Usage

InChI:InChI=1/C17H26O5/c1-2-3-4-5-6-7-8-9-10-22-17(21)13-11-14(18)16(20)15(19)12-13/h11-12,18-20H,2-10H2,1H3

Upstream product

• 112-30-1 1-Decanol 
• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 35388-10-4 3,4,5-trihydroxybenzoyl chloride 

Downstream Products

• 1329454-66-1 decyl 3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside)-4,5-dihydroxybenzoate 
• 1329454-78-5 decyl 3-O-(β-D-glucopyranosyl)-4,5-dihydroxybenzoate 

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.

Antifungal activity of alkyl gallates against plant pathogenic fungi

The antifungal activity of alkyl gallates against plant pathogenic fungi was evaluated. All of the fungi tested in this study were susceptible to some alkyl gallates, and the effect of linear alkyl gallates against plant pathogenic fungi was similar to the previously reported effects against Gram-negative and Gram-positive bacteria. We found that branched alkyl gallates showed stronger activity than did linear alkyl gallates with similar log P values. In addition, the antifungal activity of alkyl gallates was correlated with gallate-induced inhibition of the activity of mitochondrial complex II. The antifungal activity of alkyl gallates likely originates, at least in part, from their ability to inhibit the membrane respiratory chain.

ANTAGONISTS OF THE TOLL-LIKE RECEPTOR 1/2 COMPLEX

Provided are compounds, compositions and methods for treating Toll-like receptor 1/2 complex (TLRI/2) related inflammatory disorders. Small molecules, based on the benzotropolone scaffold, capable of influencing downstream signaling are dislcosed as well as methods of making and modifying these molecules. Also provided are methods for treating a subject for a clinical condition associated with Toll? like receptor complex 1/2 activation, comprising administering to the subject an effective amount of a benzotropolone compound.

Discovery of small-molecule inhibitors of the TLR1/TLR2 complex

An important regulator of innate immunity, the protein complex of Toll-like receptors 1 and 2 (TLR1/TLR2) provides an attractive target for the treatment of various immune disorders. The novel compound CU-CPT22 can compete with the binding of the specific lipoprotein ligand to TLR1/TLR2 (see picture) with high inhibitory activity and specificity. Repression of downstream signaling from TNF-α and IL-1β was also observed. Copyright

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.

Synthesis and characterization of phenolic antioxidants with surfactant properties: Glucosyl- and glucuronosyl alkyl gallates

In the search of better antioxidants for different applications, we have designed and synthesized two series of antioxidants that possess surfactant properties: glucosyl- and glucuronosyl alkyl gallates. They display better surface-active efficiency that alkyl gallates and some show critical micelle concentration (CMC) and surfactant effectiveness (γcmc) in the same range of worldwide known surfactants, such as Brij-30 or Tween-20. Moreover, they exhibit a high antioxidant activity due to the di-ortho phenolic moiety present in their structure. Nevertheless, glucosyl- and glucuronosyl alkyl gallates are worse antioxidants than the corresponding alkyl gallates.

Inhibitive effects of alkyl gallates on Hyaluronidase and collagenase

A series of the gallate esters of n-alkanols (C1-C12) was examined to determine their inhibitory activities against hyaluronidase and collagenase. Hexyl, heptyl, octyl, nonyl, and decyl gallates inhibited both hyaluronidase and collagenase, and the most potent inhibitor was octyl gallate against both enzymes. Octyl 3, 5- dihydroxybenzoate showed inhibitory effects on hyaluronidase, whereas collagenase was inhibited by octyl 3, 4-dihydroxybenzoate.

Antifeeding method against insects

Wooden material can be protected by applying a C8-C12 alkyl ester of gallic acid to the wooden material from feeding by insects.

Evaluation of anti-herpetic and antioxidant activities, and cytotoxic and genotoxic effects of synthetic alkyl-esters of gallic acid

The n-alkyl esters of gallic acid (CAS 138-57-8) have a diverse range of uses as anti-oxidants in food, cosmetics and pharmaceutical industries. Pharmaceutical studies performed with these compounds have found that they have many therapeutic potentialities including anti-cancer, antiviral and antimicrobial properties. However, more interest has been devoted to their antioxidant activity due to the ability to scavenge and reduce reactive oxygen species (ROS) formation. In this study, gallic acid and 14 different alkyl gallates were tested. The cytotoxicity and anti-herpetic (HSV-1, KOS and 29-R strains) activity were studied by using the MTT (3-(4,5-dimethylthiazol-2-yl)-2, 5-diphenyl tetrazolium bromide) colorimetric assay and the cell viability by using the Trypan blue dye exclusion method. The genotoxicity was studied by the Comet assay and the antioxidant activity by using the DPPH (1,1-diphenyl-2- picrylhydrazyl) radical scavenging and microsomal lipid peroxidation-inhibiting activities. The results showed that all the tested compounds have anti-herpetic activity at non cytotoxic concentrations with selectivity indices (SI = CC 50/EC50) varying from 0.89 to 18.34, depending on the used HSV-1 strain. It was observed that all tested alkyl gallates showed some degree of genotoxicity, at the tested concentrations, except cetyl gallate, at 256.60 μmol/L (p 50 values varying from 17 to 31 μmol/L; and microsomal lipid peroxidation-inhibiting activity with IC50 values varying from 21 to 59 μmol/L. It was observed that the presence of hydroxyl groups in these molecules is important for their pharmacological profile, but the length of the lateral carbonic chain does not have considerable influence.

Alkyl gallates, intensifiers of β-lactam susceptibility in methicillin-resistant Staphylococcus aureus

We found that ethyl gallate purified from a dried pod of tara (Caesalpinia spinosa) intensified β-lactam susceptibility in methicillin-resistant and methicillin-sensitive strains of Staphylococcus aureus (MRSA and MSSA strains, respectively). This compound and several known alkyl gallates were tested with MRSA and MSSA strains to gain new insights into their structural functions in relation to antimicrobial and β-lactam susceptibility-intensifying activities. The maximum activity of alkyl gallates against MRSA and MSSA strains occurred at 1-nonyl and 1-decyl gallate, with an MIC at which 90% of the isolates tested were inhibited of 15.6 μg/ml. At concentrations lower than the MIC, alkyl gallates synergistically elevated the susceptibility of MRSA and MSSA strains to β-lactam antibiotics. Such a synergistic activity of the alkyl gallates appears to be specific for β-lactam antibiotics, because no significant changes were observed in the MICs of other classes of antibiotics examined in this study. The length of the alkyl chain was also associated with the modifying activity of the alkyl gallates, and the optimum length was C5 to C6. The present work clearly demonstrates that the length of the alkyl chain has a key role in the elevation of susceptibility to β-lactam antibiotics.