Solubility of Gallic Acid in Methanol, Ethanol, Water, and Ethyl Acetate

Daneshfar, Ali; Ghaziaskar, Hassan S.; Homayoun, Nasrolah

doi:10.1021/je700633w

Cited by 136 publications

(116 citation statements)

References 15 publications

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“…It was observed that an increase in the temperature increased the solubility of GE, EA, and GA, regardless of the solvent used (Table 7). A similar observation was reported by Daneshfar et al (2008), whereby the solubility of gallic acid in different solvents increased correspondingly with increasing temperature.…”

Section: Equilibrium Solubility In Biorelevant Mediasupporting

confidence: 87%

“…The solubility of GE, EA, and GA was observed to be the highest in intestinal fluids (SIF: pH 6.8, FaSSIF: pH 6.5, and FeSSIF: pH 5) and the least in gastric fluid (SGF: pH 1.2). This could be due to the acidic nature of the compounds (Ascacio-Valdes et al, 2011;Daneshfar et al, 2008;Przewloka & Shearer, 2002).…”

Section: Equilibrium Solubility In Biorelevant Mediamentioning

confidence: 99%

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The physicochemical properties of geraniin, a potential antihyperglycemic agent

Elendran

Wang

Prankerd

et al. 2015

Pharmaceutical Biology

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Context: Natural products play a vital role in the discovery of leads for novel pharmacologically active drugs. Geraniin (GE) was identified as the major compound in the rind of Nephelium lappaceum L. (Sapindaceae), while ellagic and gallic acids have been shown to be its main metabolites. GE and its metabolites possess a range of bioactive properties including being an anti-infective, anticarcinogenic, antihyperglycemic, and antihypertensive. Objective: GE and its metabolites were investigated to establish its gastrointestinal absorption and physicochemical properties. Materials and methods: GE was purified from N. lappaceum rind extract using reverse-phase C18 column chromatography. Lipophilicity (log P) was determined using the 1-octanol/water shakeflask method. Equilibrium solubility of GE and its metabolites (20 mg) was determined in water and four biorelevant media: simulated gastric, simulated intestinal, fasted state-simulated intestinal, and fed state-simulated intestinal after 72 h. Results and discussion: The purification yield was 10.8%; where a 97-99% pure GE was obtained. Log P values for GE, ellagic, and gallic acids were established as À0.73 ± 0.17, 0.11 ± 0.06, and 0.71 ± 0.21, respectively, establishing them as polar compounds. All three compounds were found to exhibit poor solubility in gastric (0.61-8.10 mg/mL) but good solubility in intestinal fluids (3.59-14.32 mg/mL). Conclusion:The above results indicate that the compounds have limited gastrointestinal absorption due to its polarities. To consider these compounds as oral drug candidates, formulation strategies are being developed.

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Section: Equilibrium Solubility In Biorelevant Mediasupporting

confidence: 87%

Section: Equilibrium Solubility In Biorelevant Mediamentioning

confidence: 99%

The physicochemical properties of geraniin, a potential antihyperglycemic agent

Elendran

Wang

Prankerd

et al. 2015

Pharmaceutical Biology

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“…In contrast to the compounds mentioned below, gallic acid is highly soluble in water and in polar solvents such as ethanol or methanol (Daneshfar et al 2008). This compound is found in hornbeam and oak bark, oak apple, green or black tea, hops, pomegranate and in other plants and fruits.…”

mentioning

confidence: 99%

Use of natural substances for boar semen decontamination

Mazurová¹,

Kukla²,

Rozkot³

et al. 2015

Vet. Med. - Czech

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ABSTRACT:The aim of this study was to investigate the antibacterial activity and toxicity for sperm cells of the natural substances gallic acid, methyl gallate, ethyl gallate, propyl gallate, octyl gallate, thymol, carvacrol and eugenol. The antibacterial activity of these natural substances and selected combinations of them against bacterial strains isolated from boar ejaculates was determined using the microdilution and macrodilution method in Mueller-Hinton broth. The most effective natural substances against Gram-negative and Gram-positive bacteria included in our study were thymol and carvacrol with minimum inhibitory concentration (MIC) values in the range of 300-600 µg/ml. Gallic acid exhibited the best antibacterial activity against Pseudomonas aeruginosa strains (MIC values of 300-2400 µg/ml), whereas the ranges of MIC values against Escherichia coli, Enterococcus faecalis and Staphylococcus sp. strains were higher. Octyl gallate exhibited stronger antibacterial activity against staphylococci and enterococci (MIC values of 18.8-75 µg/ml) than against Escherichia coli and Pseudomonas aeruginosa strains with MIC values in the ranges of 300-600 µg/ml and 1200-2400 µg/ml, respectively. Thymol combined with carvacrol was the most effective combination against enterococci (MIC values of 75-300 : 150 thymol : carvacrol) and Pseudomonas aeruginosa (MIC values of 75-300 : 300 thymol : carvacrol), bacteria which are known to be frequently resistant to antimicrobials. Similar results were determined for the combination of carvacrol and eugenol against staphylococci and enterococci. The results of the combinations revealed more of an additive rather than a synergistic effect. Thymol and carvacrol were the most effective natural substances against the bacteria included in this study, with a low toxicity for sperm cells compared to other substances, suggesting their possible use for boar semen decontamination.

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“…This suggests that either AA is a stronger antioxidant than the GA or that the concentration of GA is too low to scavenge free radicals in the solution [7]. Indeed, the applied GA concentration was only 1% (w/w), but this is the maximal achievable concentration in water solution at room temperature [3]. The T 1 dependence on antioxidant concentration has been already studied in the previous work [5] for AA and glutathione additives, the recovery of T 1 relaxation time was found to be more effective at higher concentrations of these antioxidants.…”

Section: Resultsmentioning

confidence: 99%

“…The antioxidants applied were ascorbic acid (AA, vitamin C, Polskie Odczynniki Chemiczne, POCH Poland) and gallic acid (GA, Fluka Chemika Switzerland), which were used as saturated water solutions at the concentrations of 17% (w/w) and 1% (w/w), respectively [2,3].…”

Section: Methodsmentioning

confidence: 99%

Observation of Antioxidants Activity using NMR Relaxation Measurements

2018

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Formation of free radicals in biological solutions leads to the changes in water protons relaxation times. Therefore, NMR relaxation measurements were used to investigate kinetics of oxidation processes induced by the addition, in low amounts, of hydrogen peroxide (H2O2q to aqueous protein solution and to blood serum. The measured relaxation times were not stable over time because of the progressive formation of free radicals and their damaging action to the protein structure. The addition of antioxidants (ascorbic acid, gallic acid etc.) changed the relaxation time courses due to free radical scavenging. Similar time courses, thus anti-oxidant actions, were observed in various blood serum without antioxidant additive. Moreover, the observed kinetics of spin-lattice relaxation time (T1q depended on several factors, such as: structure and concentration of protein solutions and activity and concentration of the added antioxidants.

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Solubility of Gallic Acid in Methanol, Ethanol, Water, and Ethyl Acetate

Cited by 136 publications

References 15 publications

The physicochemical properties of geraniin, a potential antihyperglycemic agent

The physicochemical properties of geraniin, a potential antihyperglycemic agent

Use of natural substances for boar semen decontamination

Observation of Antioxidants Activity using NMR Relaxation Measurements

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