| Size | Price | |
|---|---|---|
| Other Sizes |
Purity: ≥98%
| Targets |
Microbial Metabolite; Bacteria (IC50 = 160 μg/mL); Endogenous Metabolite
4-Hydroxybenzoic acid does not have a specific drug target but is a naturally occurring phenolic acid that acts as a metabolic intermediate. It is involved in the shikimate pathway and is a precursor to ubiquinone and other benzoquinones. The compound has been reported to exhibit antioxidant activity by scavenging free radicals and may modulate various cellular signaling pathways. Its antimicrobial properties are well documented and are the basis for its use as a preservative. |
|---|---|
| ln Vitro |
With IC50 concentrations of 100–170 and 160 μg/mL, respectively, trans-4-hydroxycinnamic acid (4–HBA) and 4-hydroxybenzoic acid are sensitive to most Gram-positive bacteria and some Gram-negative bacteria. The antibacterial activity of 4-hydroxycinnamic acid and t4-HCA against 11 food pathogenic bacteria, 6 plant pathogenic bacteria, 2 yeasts, and 15 plant pathogenic fungi was assessed using the disc method. At 200–400 μg, these substances stop the majority of bacteria and yeast from growing. Nonetheless, the majority of Gram-positive bacteria are more susceptible to this inhibitory effect. The disk method indicates that 4-hydroxycinnamic acid exhibits greater antibacterial activity than t4-HCA against Staphylococcus aureus, Lactobacillus mesentericus, Saccharomyces cerevisiae, and Candida albicans at a concentration of 50 μg. Nevertheless, no inhibitory effect on fungi was noted, even at concentrations as high as 1000 μg [1].
4-Hydroxybenzoic acid exhibits antioxidant activity by scavenging free radicals and reducing oxidative stress. It has been shown to have anti-inflammatory properties in various in vitro models. The compound also demonstrates antimicrobial activity against a range of bacteria and fungi. It is a precursor for the synthesis of parabens, which are widely used as preservatives in pharmaceuticals and cosmetics. The compound's effects on cellular signaling pathways are still being investigated. |
| ln Vivo |
Absorption, Distribution and Excretion: ...Groups of 4-8 rabbits were given 4-hydroxybenzoic acid at a dose of 100, 250, 500, 1000, or 1500 mg/kg bw by gavage every 3-7 days. Urine was collected continuously and analysed for metabolites. The total urinary recovery of the test material ranged from 84% to 104%. Glucuronic acid and sulfate conjugates were also detected in the urine, at 10-35% and 4-7%, respectively. The concentrations of all the metabolites returned to background values within 24 hr after dosing.
Metabolism / Metabolites: In rabbits, 96% of a single oral dose of 400 mg/kg bw 4-hydroxybenzaldehyde was excreted in the urine within 24 hr as 4-hydroxybenzoic acid and its glycine, glucuronic acid, and sulfate conjugates. Metabolism in the rat of p-hydroxybenzoic acid and its methyl, ethyl and propyl esters resulted in the appearance in the urine first of free p-hydroxybenzoic acid, followed by the glucuronide and p-hydroxyhippuric acid, the concentration of which increased as that of the free p-hydroxybenzoic acid /decreased/. In vivo studies have shown that 4-hydroxybenzoic acid is metabolized and excreted in humans and animals. It is a normal constituent of the human diet and is generally recognized as safe. The compound has been studied for its potential health benefits, including antioxidant and anti-inflammatory effects. However, its in vivo pharmacological effects are modest compared to its role as a metabolic intermediate and preservative. Further research is needed to fully characterize its in vivo activities. |
| Enzyme Assay |
The in vitro assay for 4-hydroxybenzoic acid typically involves measuring its antioxidant activity using methods such as DPPH radical scavenging, ABTS radical scavenging, or FRAP (ferric reducing antioxidant power) assays. The compound is tested at various concentrations, and the antioxidant capacity is expressed as IC50 or Trolox equivalents. Antimicrobial activity is assessed using standard broth dilution or disk diffusion methods against various bacterial and fungal strains.
|
| Cell Assay |
The in vitro cellular assay for 4-hydroxybenzoic acid typically involves culturing cell lines (e.g., macrophages, endothelial cells, or cancer cells) and treating them with varying concentrations of the compound. Cellular responses such as reactive oxygen species (ROS) production, inflammatory cytokine secretion, or cell viability are measured. The compound's anti-inflammatory effects are assessed by measuring the inhibition of pro-inflammatory mediators such as TNF-α, IL-6, or NO production.
|
| Animal Protocol |
In vivo animal studies for 4-hydroxybenzoic acid typically involve the administration of the compound to rodents via oral gavage or dietary supplementation. Parameters such as antioxidant status, inflammatory markers, and metabolic profiles are assessed in blood and tissues. The compound's effects on various disease models (e.g., inflammation, diabetes, or cardiovascular disease) may be evaluated. The compound is generally well tolerated at moderate doses.
|
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
…4-8 rabbits per group were administered 4-hydroxybenzoic acid by gavage every 3-7 days at doses of 100, 250, 500, 1000, or 1500 mg/kg body weight. Urine was continuously collected and metabolites were analyzed. The total urinary recovery rate of the test substance was 84% to 104%. Glucuronic acid and sulfate conjugates were also detected in the urine at concentrations of 10-35% and 4-7%, respectively. Within 24 hours after administration, the concentrations of all metabolites returned to baseline levels. Metabolisms/Metabolites In rabbits, 96% of a single oral dose of 400 mg/kg body weight of 4-hydroxybenzoic acid was excreted in the urine within 24 hours as 4-hydroxybenzoic acid and its glycine, glucuronic acid, and sulfate conjugates. ...In rats, the metabolism of p-hydroxybenzoic acid and its methyl, ethyl and propyl esters results in the initial appearance of free p-hydroxybenzoic acid in the urine, followed by glucuronide and p-hydroxyhippuric acid, with their concentrations increasing as the concentration of free p-hydroxybenzoic acid decreases. 4-Hydroxybenzoic acid is a small molecule with a molecular weight of 138.12 g/mol and a molecular formula of C7H6O3. It is soluble in water, ethanol, and other organic solvents. The compound is metabolized and excreted in urine, primarily as conjugates (glucuronides and sulfates). It has a short half-life and is rapidly cleared from the body. The compound is generally recognized as safe (GRAS) for use in food and pharmaceutical products. |
| Toxicity/Toxicokinetics |
Non-Human Toxicity Values
Oral LD50 in mice: 2200 mg/kg Intraperitoneal LD50 in mice: 210 mg/kg Subcutaneous LD50 in mice: 1050 mg/kg 4-Hydroxybenzoic acid is generally recognized as safe (GRAS) and is widely used as a food additive and preservative in the form of its esters (parabens). It has low acute toxicity and is well tolerated at typical exposure levels. However, high doses may cause gastrointestinal irritation. The compound is not considered genotoxic or carcinogenic. It is intended for research use and as a pharmaceutical intermediate. |
| References | |
| Additional Infomation |
4-Hydroxybenzoic acid is a monohydroxybenzoic acid, meaning it contains a hydroxyl substituent at the C-4 position of the benzene ring. It is a metabolite found in both plants and algae. It is the conjugate acid of 4-hydroxybenzoic acid esters. 4-Hydroxybenzoic acid is a metabolite found or produced in Escherichia coli (strains K12 and MG1655). It has also been reported that 4-oxobenzoic acid exists in tea trees, peonies, and other organisms with relevant data. See also: Hibiscus trifoliata leaves (partial); Galium affine whole plant (partial); blueberry leaves (partial)... See more...
4-Hydroxybenzoic acid is a naturally occurring phenolic acid found in many plants, including fruits, vegetables, and herbs. It is a key intermediate in the biosynthesis of ubiquinone (coenzyme Q) and other benzoquinones. The compound is also a metabolite of certain dietary polyphenols and is excreted in urine. Its esters (parabens) are widely used as preservatives in pharmaceuticals, cosmetics, and food products. The compound is used in research as a standard for antioxidant assays and as a building block for drug synthesis. |
| Molecular Formula |
C7H6O3
|
|---|---|
| Molecular Weight |
138.1207
|
| Exact Mass |
138.031
|
| CAS # |
99-96-7
|
| Related CAS # |
4-Hydroxybenzoic acid-d4;152404-47-2;4-Hydroxybenzoic acid-13C;146672-02-8
|
| PubChem CID |
135
|
| Appearance |
White granular crystalline powder consisting of monoclinic prisms
|
| Density |
1.4±0.1 g/cm3
|
| Boiling Point |
336.2±25.0 °C at 760 mmHg
|
| Melting Point |
213-217 °C(lit.)
|
| Flash Point |
171.3±19.7 °C
|
| Vapour Pressure |
0.0±0.8 mmHg at 25°C
|
| Index of Refraction |
1.616
|
| LogP |
1.42
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
1
|
| Heavy Atom Count |
10
|
| Complexity |
125
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
O([H])C1C([H])=C([H])C(C(=O)O[H])=C([H])C=1[H]
|
| InChi Key |
FJKROLUGYXJWQN-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10)
|
| Chemical Name |
4-hydroxybenzoic acid
|
| Synonyms |
4-HYDROXYBENZOIC ACID; 99-96-7; p-Hydroxybenzoic acid; 4-Carboxyphenol; p-Salicylic acid; Benzoic acid, 4-hydroxy-; Benzoic acid, p-hydroxy-; p-carboxyphenol;
|
| 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 : ~120 mg/mL (~868.81 mM)
H2O : ~1.2 mg/mL (~8.69 mM) |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 3 mg/mL (21.72 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 30.0 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. Solubility in Formulation 2: ≥ 3 mg/mL (21.72 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 30.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. View More
Solubility in Formulation 3: ≥ 2.86 mg/mL (20.71 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. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 7.2401 mL | 36.2004 mL | 72.4008 mL | |
| 5 mM | 1.4480 mL | 7.2401 mL | 14.4802 mL | |
| 10 mM | 0.7240 mL | 3.6200 mL | 7.2401 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.
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