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| Other Sizes |
| Targets |
2,2-Dihydroxy-1-phenylethan-1-one targets mitochondrial aldehyde dehydrogenase, acting as a potent inhibitor. It also reacts with arginine residues in purified Hageman factor (HF, Factor XII), causing inhibition of its coagulant properties. The compound's antioxidant activity suggests it may also target oxidative stress pathways. It is used as a specific reagent for arginine groups in protein modification studies.
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| ln Vitro |
In vitro, 2,2-Dihydroxy-1-phenylethan-1-one is a potent inhibitor of mitochondrial aldehyde dehydrogenase. It reacts with arginine residues in purified Hageman factor and causes inhibition of its coagulant properties. The compound exhibits antioxidant activity. It is used to modify proteins such as pig muscle carbonic anhydrase III and to prepare pyrrolinone and furan derivatives. Specific IC50 values are not detailed.
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| ln Vivo |
Specific in vivo data for 2,2-Dihydroxy-1-phenylethan-1-one are limited. As an aldehyde dehydrogenase inhibitor, the compound would have potential for in vivo studies in alcohol metabolism and aldehyde toxicity models. However, specific published in vivo protocols for this compound are not detailed. The compound is primarily used as a research reagent for protein modification and enzyme inhibition studies.
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| Enzyme Assay |
The aldehyde dehydrogenase inhibitory activity is assessed using biochemical enzyme assays. Mitochondrial aldehyde dehydrogenase is incubated with the substrate (e.g., acetaldehyde or propionaldehyde) and NAD⁺ in the presence of various concentrations of 2,2-Dihydroxy-1-phenylethan-1-one. The production of NADH is measured spectrophotometrically at 340 nm, and IC50 values are calculated from dose-response curves. The compound is used as a specific reagent for arginine residues in protein modification studies.
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| Cell Assay |
For cellular studies, various cell lines may be used to assess the compound's effects on aldehyde dehydrogenase activity and oxidative stress. Cells are treated with the compound at various concentrations (e.g., 0.1-10 mM) for 24-72 hours. Cell viability is assessed using MTT or similar assays. Aldehyde dehydrogenase activity is measured in cell lysates. ROS levels are measured using DCFH-DA. The compound is typically dissolved in water or ethanol and diluted in culture media. The compound has a molecular weight of 152.15 g/mol (as hydrate) or 134.13 g/mol (anhydrous).
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| Animal Protocol |
In vivo studies for 2,2-Dihydroxy-1-phenylethan-1-one would be conducted in appropriate animal models. For aldehyde dehydrogenase inhibition studies, models of alcohol metabolism or aldehyde toxicity would be used. The compound would be administered via intraperitoneal injection or oral gavage. However, specific published protocols for this compound are not available. The compound is primarily used as a research reagent.
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| ADME/Pharmacokinetics |
Specific pharmacokinetic data for 2,2-Dihydroxy-1-phenylethan-1-one are not reported. The compound has a molecular weight of 152.15 g/mol (as hydrate) or 134.13 g/mol (anhydrous basis). As a small reactive compound, it is expected to be rapidly metabolized. Pharmacokinetic studies would be required to determine parameters such as half-life and clearance. The compound should be stored at room temperature or as specified by the manufacturer.
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| Toxicity/Toxicokinetics |
Specific toxicological data for 2,2-Dihydroxy-1-phenylethan-1-one are not extensively reported. As a reactive compound that modifies proteins, it should be handled with caution. The compound is a potent inhibitor of mitochondrial aldehyde dehydrogenase, and inhibition of this enzyme can lead to accumulation of toxic aldehydes. Standard safety precautions should be taken when handling, including the use of gloves, eye protection, and proper ventilation.
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| References |
[1]. Tania Kundu, et al. Expeditious and eco-friendly synthesis of new multifunctionalized pyrrole derivatives and evaluation of their antioxidant property. Bioorg Chem. 2020 May;98:103734.
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| Additional Infomation |
See also: 2',3'-Dihydroxyacetophenone (note moved to).
2,2-Dihydroxy-1-phenylethan-1-one (Phenylglyoxal hydrate) is a potent mitochondrial aldehyde dehydrogenase inhibitor and arginine-specific protein modifier. It exhibits antioxidant activity. MW: 152.15 (hydrate). For research use only. |
| Molecular Formula |
C8H8O3
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|---|---|
| Molecular Weight |
152.15
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| Exact Mass |
152.047
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| CAS # |
1075-06-5
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| PubChem CID |
99611
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| Appearance |
White to light yellow solid powder
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| Density |
1.307 g/cm3
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| Boiling Point |
142 °C125 mm Hg(lit.)
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| Melting Point |
76-79 °C(lit.)
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| Flash Point |
142°C/125mm
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| Vapour Pressure |
0.00469mmHg at 25°C
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| Index of Refraction |
1.59
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| LogP |
1.003
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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 |
2
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| Heavy Atom Count |
11
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| Complexity |
136
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=CC=C(C=C1)C(=O)C(O)O
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| InChi Key |
NBIBDIKAOBCFJN-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,8,10-11H
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| Chemical Name |
2,2-dihydroxy-1-phenylethanone
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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: 250 mg/mL (1643.12 mM)
H2O: 25 mg/mL (164.31 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (13.67 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 (13.67 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 (13.67 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 20 mg/mL (131.45 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.5725 mL | 32.8623 mL | 65.7246 mL | |
| 5 mM | 1.3145 mL | 6.5725 mL | 13.1449 mL | |
| 10 mM | 0.6572 mL | 3.2862 mL | 6.5725 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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