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| Other Sizes |
| Targets |
Phenylglyoxylic acid targets multiple enzymes and pathways. It notably influences pathways related to pyruvate metabolism. It inhibits Yersinia Protein-tyrosine phosphatase 1B with an IC50 of 2700 µM and glycolic acid oxidase with an IC50 of 2.29 µM. The compound shows less potent inhibition of recombinant His6-tagged CtBP2 dehydrogenase and Staphylococcus aureus pyruvate carboxylase, with IC50 values exceeding 300 µM and 3000 µM respectively. As a metabolite of ethylbenzene and styrene, it serves as a human endogenous metabolite.
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| ln Vitro |
In vitro, Phenylglyoxylic acid stimulates pyruvate oxidation in rat diaphragm tissues at varying concentrations. It inhibits glycolic acid oxidase with an IC50 of 2.29 µM. The compound serves as a drug intermediate for the synthesis of antineoplastic compounds. It is used as a metal-chelating agent with anti-inflammatory properties. Its solubility in DMSO is 30 mg/mL (199.82 mM).
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| ln Vivo |
In vivo, Phenylglyoxylic acid enhances pyruvate dehydrogenase activity when administered subcutaneously. It exhibits anti-inflammatory activity in rats formalin-induced paw swelling model at doses of 50-200 mg/kg administered orally. The compound reduced the degree of hind paw swelling in rats when given in three doses (48 h, 24 h and 30 min before formalin administration).
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| Enzyme Assay |
In vitro enzyme assays for Phenylglyoxylic acid typically measure its inhibition of target enzymes such as glycolic acid oxidase and protein tyrosine phosphatase 1B. Enzyme activity is assessed by monitoring substrate conversion using spectrophotometric methods. The compound is added at varying concentrations, and IC50 values are calculated from dose-response curves. For glycolic acid oxidase inhibition, the IC50 of 2.29 µM is determined through these assays. Binding to divalent metal ions can be assessed using spectroscopic methods. Assays are performed in appropriate buffer systems with positive controls.
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| Cell Assay |
In vitro cell-based assays for Phenylglyoxylic acid are conducted in various cell lines to study its metabolic and anti-inflammatory effects. Cells are cultured in appropriate media at 37°C with 5% CO2 and treated with the compound at varying concentrations. Pyruvate metabolism and dehydrogenase activity are assessed by measuring metabolic intermediates. Anti-inflammatory activity is evaluated by measuring cytokine production. Cell viability is assessed by standard assays such as MTT. Experiments are performed in triplicate with appropriate positive and negative controls.
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| Animal Protocol |
In vivo animal studies for Phenylglyoxylic acid are conducted in rodent models. For anti-inflammatory evaluation, formalin-induced paw swelling model in rats is used. Animals are treated with the compound orally at doses of 50-200 mg/kg. Hind paw swelling is measured to assess anti-inflammatory efficacy. For metabolic studies, the compound is administered subcutaneously to assess pyruvate dehydrogenase activity. Animals are monitored for clinical signs. Blood and tissue samples are collected for biochemical analysis. Studies are conducted in accordance with institutional animal care guidelines.
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| ADME/Pharmacokinetics |
Phenylglyoxylic acid (MW 150.13 g/mol, C8H6O3) is soluble in DMSO at 30 mg/mL (199.82 mM). It has a density of 1.298 g/cm3. The compound is stable as a powder at -20°C for 3 years and in solvent at -80°C for 1 year. For in vivo administration, it can be formulated in 10% DMSO + 40% PEG300 + 5% Tween 80 + 45% saline. ADMET properties show positive blood-brain barrier penetration (0.6250) and 74.29% human oral bioavailability.
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| Toxicity/Toxicokinetics |
Phenylglyoxylic acid has an intravenous LD50 of 180 mg/kg in mice. It is a skin and strong eye irritant. In a three-month oral dosing study, male Wistar rats were dosed with 0, 1250, 3750 or 5000 mg/L of phenylglyoxylic acid in drinking water. The compound is considered a probable, possible or confirmed human carcinogen by IARC. Causes skin and serious eye irritation, and may cause respiratory irritation.
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| References | |
| Additional Infomation |
Phenylacetic acid (PGA) is a 2-oxomonocarboxylic acid, a compound formed by replacing the aldehyde hydrogen atom of glyoxylate with a phenyl group. It serves as a heterologous metabolite and biomarker in humans. Its function is related to glyoxylate; it is the conjugate acid of phenylglyoxylate esters. Benzoylcarboxylic acid has been reported in European grapes (Vitis vinifera), and relevant data exist. Phenylacetic acid is an aromatic hydrocarbon composed of compounds formed by replacing the aldehyde hydrogen atom of glyoxylate with a phenyl group. Since PGA is a metabolite of styrene, the measurement of PGA in urine may be related to the subject's styrene exposure level.
Phenylglyoxylic acid (Benzoylformic acid) is a metabolite of ethylbenzene and styrene (EB/S) and can be used as a biomarker of exposure to EB/S in humans. It serves as a drug intermediate for the synthesis of antineoplastic compounds. The compound is utilized to investigate catalytic mechanisms, substrate specificity, and enzyme kinetics in the benzoate catabolic pathway. Its conjugate base, benzoylformate, is the substrate of benzoylformate decarboxylase, a thiamine diphosphate-dependent enzyme. All applications are limited to non-human research use. |
| Molecular Formula |
C8H6O3
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|---|---|
| Molecular Weight |
150.1314
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| Exact Mass |
150.031
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| CAS # |
611-73-4
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| Related CAS # |
Phenylglyoxylic acid sodium;43165-51-1;Phenylglyoxylic acid-d5;1217089-53-6;Phenylglyoxylic acid-d5 sodium;2708283-39-8
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| PubChem CID |
11915
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| Appearance |
Off-white to light yellow solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
258.6±13.0 °C at 760 mmHg
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| Melting Point |
62-65 °C(lit.)
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| Flash Point |
124.4±16.3 °C
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| Vapour Pressure |
0.0±0.6 mmHg at 25°C
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| Index of Refraction |
1.569
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| LogP |
0.69
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
11
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| Complexity |
168
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
FAQJJMHZNSSFSM-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C8H6O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5H,(H,10,11)
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| Chemical Name |
2-oxo-2-phenylacetic 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 : ~50 mg/mL (~333.04 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (16.65 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 (16.65 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 (16.65 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 | 6.6609 mL | 33.3045 mL | 66.6089 mL | |
| 5 mM | 1.3322 mL | 6.6609 mL | 13.3218 mL | |
| 10 mM | 0.6661 mL | 3.3304 mL | 6.6609 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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