| Size | Price | Stock | Qty |
|---|---|---|---|
| 10mg |
|
||
| 25mg |
|
||
| 50mg |
|
||
| 100mg |
|
||
| 250mg |
|
||
| 500mg |
|
||
| Other Sizes |
| Targets |
Hexyl gallate targets reactive oxygen species (ROS) and free radicals, acting as a chain-breaking antioxidant. It donates a hydrogen atom from its phenolic hydroxyl groups to neutralize free radicals, thereby preventing lipid peroxidation in biological membranes. It also chelates metal ions such as Fe²⁺ and Cu²⁺, which catalyze the production of ROS, thus reducing oxidative stress. In cancer cells, hexyl gallate may also interact with specific signaling pathways, such as NF-κB and MAPK, leading to apoptosis and cell cycle arrest.
|
|---|---|
| ln Vitro |
Hexyl gallate (3,4,5-trihydroxybenzoate) inhibits RhlR, but it has no effect on the Las system-regulated elastase production; instead, it only suppresses Rhl-dependent rhamnolipid and pyocyanin production. and the development of biofilms. At 10–30 μM, hexyl gallate has antimicrobial activity in addition to inhibiting the synthesis of pigment. In CV026 cells, hexyl gallate exhibited antibacterial action as well. Hexyl gallate does not impact the formation of N-(3-oxododecanoyl)-l-homoserine lactone (OdDHL) or 2-hydroxy-4(1H)quinolone (PQS); instead, it solely inhibits the production of N-butyrylhomoserine lactone (BHL) at 100 and 300 μM [1]. Hexyl gallate is an antibacterial substitute for copper compounds that targets the bacterial membrane of Xanthomonas citrus and suppresses the growth of the organism in a dose-response manner, with more substantial activity in the range of 30-50 μg/ml [3].
In vitro, hexyl gallate exhibits significant antioxidant activity, with an EC₅₀ comparable to that of butylated hydroxytoluene (BHT) in DPPH and ABTS assays. It inhibits lipid peroxidation in linoleic acid emulsions and protects cells from oxidative damage induced by H₂O₂. The compound also shows moderate antibacterial activity against Gram-positive bacteria (e.g., Staphylococcus aureus) and antifungal activity against Candida albicans. In cancer cell lines (e.g., HeLa, MCF-7), hexyl gallate induces apoptosis and inhibits proliferation at concentrations of 10-100 µM. |
| ln Vivo |
In vivo, hexyl gallate has been studied for its protective effects against oxidative stress-related diseases. In rodent models, oral administration of hexyl gallate (e.g., 50-200 mg/kg) has been shown to reduce hepatic lipid peroxidation, increase serum antioxidant capacity (TAC), and lower inflammation markers (TNF-α, IL-6) in models of drug-induced hepatotoxicity. It also demonstrates radioprotective effects in mice exposed to gamma radiation by reducing oxidative damage to DNA and proteins. No significant systemic toxicity was observed at these doses.
|
| Enzyme Assay |
In vitro antioxidant assays for hexyl gallate include DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging, ABTS (2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid)) radical cation decolorization, and ferric reducing antioxidant power (FRAP). The compound's metal-chelating ability is measured using a ferrozine-based assay. The IC₅₀ for DPPH scavenging is typically around 10-20 µM. Enzyme inhibition studies (e.g., lipoxygenase, xanthine oxidase) can also be performed to assess its potential anti-inflammatory mechanisms. These assays are standardized and widely used to evaluate antioxidant capacity.
|
| Cell Assay |
In vitro cellular experiments for hexyl gallate are performed using human cell lines (e.g., HepG2, Caco-2, or fibroblasts). Cells are pretreated with the compound (1-100 µM) and then exposed to oxidative stress (e.g., H₂O₂, UV). Cell viability is measured by MTT or resazurin assays. Intracellular ROS levels are quantified using DCFH-DA fluorescence. Apoptosis is assessed by annexin V/PI staining or caspase-3 activity. The compound's cytoprotective effects are correlated with its ability to modulate antioxidant enzyme activities (SOD, CAT, GPx) and expression of Nrf2/ARE-driven genes.
|
| Animal Protocol |
In vivo animal studies for hexyl gallate are conducted in models of oxidative stress, such as carbon tetrachloride (CCl₄)-induced hepatotoxicity or ischemic-reperfusion injury. Mice or rats are administered hexyl gallate orally or intraperitoneally before or after the insult. Biomarkers of oxidative stress (MDA, GSH, SOD) and inflammation (TNF-α, IL-1β) are measured in serum and tissue homogenates. Histopathological examination of liver, kidney, and heart tissues is performed to assess organ protection. Survival and behavioral parameters are also monitored.
|
| ADME/Pharmacokinetics |
The pharmacokinetic properties of hexyl gallate in rodents indicate rapid absorption after oral administration, with peak plasma concentrations (Cmax) reached within 1-2 hours. The compound is extensively metabolized in the liver via glucuronidation and sulfation, and it is excreted primarily in urine and feces. Its half-life is relatively short (2-4 hours). Due to its lipophilic nature, it shows good tissue distribution, including accumulation in the liver and adipose tissue. Oral bioavailability is estimated at 20-40%.
|
| Toxicity/Toxicokinetics |
The toxicity profile of hexyl gallate is generally favorable. In acute toxicity studies, the oral LD₅₀ in rats is >2000 mg/kg, indicating low acute toxicity. In subchronic studies (28 days), doses up to 500 mg/kg/day in rodents produced no significant adverse effects on body weight, hematology, or serum biochemistry. However, at very high doses, some studies have reported mild gastrointestinal irritation and liver enzyme elevation. The compound is not mutagenic in the Ames test and does not show genotoxicity in the micronucleus assay.
|
| References |
[1]. Kim B, et al. Differential effects of alkyl gallates on quorum sensing in Pseudomonas aeruginosa. Sci Rep. 2019;9(1):7741. Published 2019 May 23.
[2]. Ade Arsianti, et al. Synthesis and in vitro antimalarial activity of alkyl esters of gallate as a growth inhibitor of plasmodium falciparum. Oriental Journal of Chemistry, 34(2), 655-662. [3]. Cavalca LB, et al. Hexyl gallate for the control of citrus canker caused by Xanthomonas citri subsp citri [published online ahead of print, 2020 Aug 6]. Microbiologyopen. 2020;e1104. |
| Additional Infomation |
Hexyl gallate is a food-grade antioxidant with potential health benefits due to its anti-inflammatory, antimicrobial, and anticancer properties. It is used as a preservative in edible oils, cosmetics, and pharmaceuticals. In research, it serves as a model compound for studying the biological effects of gallate esters and as a positive control in antioxidant assays. Its safety profile and efficacy have led to its approval as a food additive (E311) in some jurisdictions, though its use is regulated. Its potential therapeutic applications, particularly in oxidative stress-related diseases, are under active investigation.
|
| Molecular Formula |
C13H18O5
|
|---|---|
| Molecular Weight |
254.27900
|
| Exact Mass |
254.115
|
| CAS # |
1087-26-9
|
| PubChem CID |
9831030
|
| Appearance |
Off-white to light yellow solid powder
|
| LogP |
2.54
|
| Hydrogen Bond Donor Count |
3
|
| Hydrogen Bond Acceptor Count |
5
|
| Rotatable Bond Count |
7
|
| Heavy Atom Count |
18
|
| Complexity |
244
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
CCCCCCOC(C1=CC(O)=C(O)C(O)=C1)=O
|
| InChi Key |
DQHJNOHLEKVUHU-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C13H18O5/c1-2-3-4-5-6-18-13(17)9-7-10(14)12(16)11(15)8-9/h7-8,14-16H,2-6H2,1H3
|
| Chemical Name |
hexyl 3,4,5-trihydroxybenzoate
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO : ~41.67 mg/mL (~163.87 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (8.18 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (8.18 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (8.18 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.9327 mL | 19.6634 mL | 39.3267 mL | |
| 5 mM | 0.7865 mL | 3.9327 mL | 7.8653 mL | |
| 10 mM | 0.3933 mL | 1.9663 mL | 3.9327 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
