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| Targets |
4-Hydroxybenzoic acid itself does not bind to a specific therapeutic target but is known to exhibit antimicrobial properties. Studies have demonstrated that unlabeled 4-hydroxybenzoic acid can inhibit most Gram-positive bacteria and some Gram-negative bacteria, with an IC50 value of 160 microg/mL. The compound's mechanism of action is thought to involve disruption of microbial cell membrane function and inhibition of key metabolic enzymes, though the exact molecular targets remain poorly defined. For the isotopically labeled version, 4-Hydroxybenzoic acid-13C6, the target is not a biological receptor but rather serves as an analytical probe. It is chemically and functionally identical to the unlabeled compound, meaning any biological activity against bacterial species would be preserved, but its intended use is strictly as a research tool.
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| ln Vitro |
In vitro antibacterial activity has been reported for unlabeled 4-hydroxybenzoic acid, with an IC50 of 160 microg/mL against a range of Gram-positive and some Gram-negative bacteria. For the isotopically labeled 13C6 version, no specific in vitro activity studies have been conducted beyond its role as a standard. However, because the isotopic substitution does not alter the chemical structure, it is reasonable to assume that 4-Hydroxybenzoic acid-13C6 retains the same antibacterial properties. In research contexts, the compound is not typically tested for activity in the same manner as a drug candidate; instead, it is used to spike into biological samples to quantify the amount of unlabeled 4-hydroxybenzoic acid or its metabolites (such as conjugates with glucuronic acid or sulfate) that may be present. This is essential for understanding the disposition of parabens or other benzoate derivatives in biological systems.
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| ln Vivo |
Published literature does not describe any dedicated in vivo studies for 4-Hydroxybenzoic acid-13C6. As a stable isotope-labeled compound intended for analytical use, it is not administered as a therapeutic in animal models. However, the compound could theoretically be used as a tracer in pharmacokinetic studies of related compounds, such as parabens. In such a scenario, the labeled compound would be administered to animals (e.g., rats or mice) by oral gavage or intravenous injection to mimic human dietary or pharmaceutical exposure to parabens. The animals would then be sacrificed at predetermined time points, and the distribution and metabolism of the labeled compound would be tracked by mass spectrometry. Such studies would reveal how 4-hydroxybenzoic acid is absorbed, metabolized (e.g., by conjugation), and excreted.
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| Enzyme Assay |
The use of 4-Hydroxybenzoic acid-13C6 in cell-free systems is limited to its function as an analytical standard. A typical experimental protocol for its use involves preparing a standard curve by diluting the compound in a suitable solvent, such as methanol or acetonitrile, to a series of known concentrations. These standard solutions are then spiked into blank biological matrix (e.g., plasma, urine, or cell lysate) to mimic real samples. After protein precipitation with an organic solvent and centrifugation, the supernatant is injected into an LC-MS/MS system. The mass spectrometer is set to monitor the mass transitions specific to the labeled compound (which will be +6 Da heavier than the unlabeled version). The ratio of the peak area of the target analyte to that of the internal standard is used to generate a calibration curve, allowing for absolute quantitation.
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| Cell Assay |
In vitro cell-based studies using 4-Hydroxybenzoic acid-13C6 are performed not to assess the compound's activity, but to measure the cellular metabolism of 4-hydroxybenzoic acid or related esters. A typical protocol involves growing cells (e.g., hepatocytes or intestinal Caco-2 cells) in culture media. The labeled compound is added to the culture medium at a defined concentration for a specified period (e.g., 1-24 hours). After treatment, the media is collected, and cells are harvested, washed, and lysed. The labeled compound and any labeled metabolites (such as 4-hydroxybenzoic acid glucuronide or sulfate) are extracted from the media and cell lysates using solid-phase extraction or protein precipitation. These extracts are then analyzed by LC-MS/MS, where the labeled internal standard (if not already present in the sample) is used to account for any losses during sample preparation. This setup allows researchers to quantify the accumulation of 4-hydroxybenzoic acid in cells and its rate of conversion to conjugated metabolites.
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| Animal Protocol |
As 4-Hydroxybenzoic acid-13C6 is not a drug substance, there are no dedicated animal study protocols for testing its efficacy. However, it is frequently used in quantitative bioanalysis as part of larger animal studies evaluating the safety or pharmacokinetics of paraben preservatives or other benzoate derivatives. A generic animal protocol involving this compound would be as follows: The labeled 4-Hydroxybenzoic acid-13C6 is dissolved in a suitable vehicle, such as saline or a water-based buffer, at a known concentration. It is administered to rodents (e.g., Sprague-Dawley rats) either by oral gavage (to simulate ingestion of parabens) or intravenous injection (to assess systemic distribution). Blood is collected at multiple time points from 0 to 24 hours. Plasma is isolated and stored at -80degC. At the end of the experiment, the animals are euthanized, and organs of interest (liver, kidney, and brain) are harvested. The labeled compound is used as an internal standard to spike the collected plasma and tissue homogenates before LC-MS/MS analysis to quantify the concentrations of the dosed compound and its metabolites.
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| ADME/Pharmacokinetics |
Detailed pharmacokinetic (PK) parameters for 4-Hydroxybenzoic acid-13C6 in animals or humans have not been reported, as it is not a drug candidate but an analytical standard. However, based on the unlabeled 4-hydroxybenzoic acid, which is well-absorbed orally and undergoes rapid first-pass metabolism, the labeled version is expected to have a short half-life in vivo. It is primarily metabolized by conjugation with glucuronic acid or sulfate in the liver, forming water-soluble metabolites that are eliminated in urine. The compound is highly water-soluble at physiological pH, which suggests a moderate volume of distribution (confined mainly to extracellular fluid). Its protein binding is low. For research applications, the stability of the compound in solution is good; it can be stored as a powder at -20degC for up to three years and in solution at -80degC for six months, protected from light.
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| Toxicity/Toxicokinetics |
Acute toxicity data specifically for 4-Hydroxybenzoic acid-13C6 are unavailable, as it is a stable isotope-labeled chemical used only in research settings. The unlabeled parent compound, 4-hydroxybenzoic acid, is generally recognized as safe (GRAS) by the FDA when used as a food preservative in low concentrations, and it is a natural constituent of many foods. Consequently, the isotopically labeled version is presumed to have a similarly low toxicity profile. The presence of 13C labeling does not alter the compound's chemical reactivity or toxicity. Nonetheless, as with any research chemical, appropriate handling precautions should be taken. It should be noted that 4-hydroxybenzoic acid is a primary metabolite of parabens, which are generally considered safe at permitted levels. The compound is not intended for human or veterinary use and is not approved for therapeutic applications.
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| References | |
| Additional Infomation |
4-Hydroxybenzoic acid-13C6 (CAS No. 287399-29-5) is a compound with a purity of ≥98%, characterized by the uniform labeling of the benzene ring with six 13C atoms, resulting in a molecular weight increase of +6 Da relative to the unlabeled molecule (138.12 g/mol). Synonyms include 4-Hydroxybenzoic-(ring-13C6) acid and Paraben-13C6. The compound is supplied as a solid and should be stored in a cool, dry place at -20degC for long-term stability. In addition to its antimicrobial properties, unlabeled 4-hydroxybenzoic acid serves as a key intermediate in the chemical industry for the production of parabens, liquid crystal polymers, and other specialty chemicals. The isotopically labeled version is an essential tool for regulatory studies requiring rigorous quantitative analysis, such as those supporting Abbreviated New Drug Applications (ANDA). No clinical trials or regulatory approvals exist for this compound, as it is exclusively a research reagent.
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| Molecular Formula |
C13C6H6O3
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| Molecular Weight |
144.08
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| Exact Mass |
144.052
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| CAS # |
287399-29-5
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| PubChem CID |
71308855
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| Appearance |
Typically exists as solids at room temperature
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| LogP |
1.09
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
10
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| Complexity |
125
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| Defined Atom Stereocenter Count |
0
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| SMILES |
[13CH]1=[13CH][13C](=[13CH][13CH]=[13C]1C(=O)O)O
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| InChi Key |
FJKROLUGYXJWQN-IDEBNGHGSA-N
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| InChi Code |
InChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10)/i1+1,2+1,3+1,4+1,5+1,6+1
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| Chemical Name |
4-hydroxy(1,2,3,4,5,6-13C6)cyclohexa-1,3,5-triene-1-carboxylic acid
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| Synonyms |
Paraben-13C6
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.9406 mL | 34.7029 mL | 69.4059 mL | |
| 5 mM | 1.3881 mL | 6.9406 mL | 13.8812 mL | |
| 10 mM | 0.6941 mL | 3.4703 mL | 6.9406 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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