| Size | Price | Stock | Qty |
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| 1g |
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| Other Sizes |
| Targets |
3-Phenylbutyric acid is often cited as a histone deacetylase (HDAC) inhibitor, a function it shares with its isomer, 4-phenylbutyric acid (4-PBA). However, it is crucial to distinguish between the two, as 4-PBA is a markedly more potent HDAC inhibitor than 3-PBA. While some sources list it as an HDAC inhibitor, others classify it primarily as an endogenous metabolite. Its effects may also involve other receptors such as VDR and PPARγ.
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| ln Vitro |
3-Phenylbutyric acid exhibits antibacterial activity with specific inhibitory activity against Helicobacter pylori and Escherichia coli. Importantly, it does not influence the growth of beneficial bacteria like Bifidobacterium and Lactobacillus. It also exhibits low cytotoxicity, with a CC50 greater than 2 mM in human U937 cells. It shows low antiproliferative activity against human U937 cells, with a CC50 greater than 2,000,000 nM. Its biological properties are influenced by its chirality, with only the (R)-enantiomer supporting the growth of Rhodococcus rhodochrous PB1.
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| ln Vivo |
In vivo, 3-phenylbutyric acid is known to undergo metabolism through initial oxidation processes involving both its benzene ring and side chain. It has been demonstrated that the compound can serve as an effective agent for the isolation of Rhodococcus rhodochrous PB1 from compost soil. Studies have also utilized it as a selective substrate for this bacterium. Its role as a bacterial xenobiotic metabolite suggests it is processed by microorganisms in the environment.
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| Enzyme Assay |
For non-cellular assays, the compound's antibacterial activity can be evaluated using standard broth microdilution methods to determine the minimum inhibitory concentration (MIC) against pathogens like H. pylori. Its potential role as an HDAC inhibitor can be assessed using in vitro enzyme assays with recombinant HDAC enzymes and a fluorogenic substrate. The compound itself can serve as a substrate for studying enantioselective metabolism by bacteria like Rhodococcus rhodochrous PB1.
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| Cell Assay |
In vitro cellular assays can be performed in cell lines such as human U937 cells to assess cytotoxicity and antiproliferative effects. Cells are treated with the compound over a range of concentrations, and cell viability is measured using standard assays like MTT or CellTiter-Glo after defined exposure periods. The compound's antibacterial activity is evaluated using standard broth microdilution methods to determine the minimum inhibitory concentration (MIC) against pathogens like H. pylori and E. coli.
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| Animal Protocol |
In vivo experiments have been conducted to study the compound's metabolism and biological effects. One study investigated its metabolism by administering it to the yeast Trichosporon asahii B1, isolated from oil-contaminated sediments. Studies have also utilized 3-PBA as a selective substrate to isolate the bacterium Rhodococcus rhodochrous PB1 from compost soil. The compound's metabolism, involving initial oxidation of the benzene ring and side chain, has been studied in these contexts.
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| ADME/Pharmacokinetics |
3-Phenylbutyric acid is a prodrug that is metabolized, mainly in the liver and kidneys. It is first converted to phenylbutyryl-CoA and then metabolized by mitochondrial beta-oxidation to the active form, phenylacetate. Phenylacetate then conjugates with glutamine to form phenylacetylglutamine, which is eliminated in the urine. For in vivo formulation, it can be dissolved in a vehicle such as 10% DMSO + 40% PEG300 + 5% Tween 80 + 45% saline.
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| Toxicity/Toxicokinetics |
The compound is classified as a skin irritant (H315), eye irritant (H319), and may cause respiratory irritation (H335). It is also categorized as having acute toxicity (H302). Precautionary statements and safety data sheets should be consulted before handling the compound. It exhibits low cytotoxicity, with a CC50 greater than 2 mM in human U937 cells.
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| References | |
| Additional Infomation |
3-Phenylacetic acid is a monocarboxylic acid, formed by the substitution of butyric acid at the 3-position with a phenyl group. It possesses antibacterial activity and is a xenobiotic metabolite of bacteria. It belongs to the benzene family of compounds and is a monocarboxylic acid. Its function is related to that of 3-phenylpropionic acid.
3-Phenylbutyric acid is a positional isomer of 4-phenylbutyric acid (4-PBA) and is not interchangeable with it. 4-PBA is a markedly more potent HDAC inhibitor than 3-PBA. 3-PBA itself is used as a chiral building block for the asymmetric synthesis of compounds like (-)-malyngolide and stereoisomers of β-methylphenylalanine. It is also known as (±)-β-Methylhydrocinnamic acid. |
| Molecular Formula |
C₁₀H₁₂O₂
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|---|---|
| Molecular Weight |
164.20
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| Exact Mass |
164.083
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| CAS # |
4593-90-2
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| PubChem CID |
20724
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| Appearance |
White to off-white solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
288.0±0.0 °C at 760 mmHg
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| Melting Point |
35-38 °C(lit.)
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| Flash Point |
170.2±13.9 °C
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| Vapour Pressure |
0.0±0.6 mmHg at 25°C
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| Index of Refraction |
1.531
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| LogP |
2.19
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
12
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| Complexity |
148
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
ZZEWMYILWXCRHZ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C10H12O2/c1-8(7-10(11)12)9-5-3-2-4-6-9/h2-6,8H,7H2,1H3,(H,11,12)
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| Chemical Name |
3-phenylbutanoic acid
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| Synonyms |
3Phenylbutyric acid; 3 Phenylbutyric acid
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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) |
DMSO : ~100 mg/mL (~609.01 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (15.23 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 25.0 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: ≥ 2.5 mg/mL (15.23 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 25.0 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (15.23 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 | 6.0901 mL | 30.4507 mL | 60.9013 mL | |
| 5 mM | 1.2180 mL | 6.0901 mL | 12.1803 mL | |
| 10 mM | 0.6090 mL | 3.0451 mL | 6.0901 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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