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| Targets |
3',4'-Dihydroxyacetophenone targets tyrosinase, an enzyme critical for melanin biosynthesis, with an IC50 of 10 μM. It also targets platelet aggregation pathways, functioning as a platelet aggregation inhibitor. Additional targets include inflammatory mediators and pathways involved in cardiac arrhythmia, with demonstrated anti-arrhythmia activity. The compound's antioxidant properties suggest it may also target reactive oxygen species and oxidative stress pathways. These diverse targets make it a multi-functional bioactive compound.
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| ln Vitro |
In vitro, 3',4'-Dihydroxyacetophenone exhibits potent tyrosinase inhibitory activity with an IC50 of 10 μM, making it effective for studying melanogenesis inhibition. It demonstrates significant antioxidant activity, scavenging free radicals and protecting cells from oxidative damage. The compound also shows anti-inflammatory activity in cell-based assays. Its ability to inhibit platelet aggregation in vitro suggests potential antithrombotic applications. These activities support its use in research on pigmentation disorders, inflammation, and cardiovascular diseases.
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| ln Vivo |
In vivo, 3',4'-Dihydroxyacetophenone has demonstrated anti-arrhythmia activity in animal models, suggesting potential cardiovascular benefits. Its anti-inflammatory and antioxidant properties may contribute to protective effects in various disease models. The compound's vasoactive properties indicate it may influence blood pressure and vascular function in vivo. However, detailed in vivo efficacy and pharmacokinetic data are limited. Further studies are needed to fully characterize its therapeutic potential and mechanisms of action in living systems.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for 3',4'-Dihydroxyacetophenone include tyrosinase inhibition assays using mushroom tyrosinase and L-DOPA as substrate. The compound is incubated with the enzyme at concentrations ranging from 0.1-100 μM, and the reaction rate is measured spectrophotometrically at 475 nm. The IC50 for tyrosinase inhibition is determined to be approximately 10 μM. Antioxidant activity is assessed using DPPH radical scavenging assays or ABTS assays. Anti-inflammatory activity is evaluated by measuring inhibition of COX-1/COX-2 or cytokine production in vitro. Platelet aggregation inhibition is assessed using platelet-rich plasma and aggregation inducers.
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| Cell Assay |
In vitro cell-based assays for 3',4'-Dihydroxyacetophenone are conducted using melanocytes (e.g., B16F10 melanoma cells) for melanogenesis studies, or macrophages for anti-inflammatory studies. Cells are treated with compound concentrations ranging from 1-100 μM for 24-72 hours. Melanin content and tyrosinase activity are measured in melanocytes. Anti-inflammatory activity is assessed by measuring pro-inflammatory cytokine levels (e.g., TNF-α, IL-6) using ELISA. Cell viability is assessed using MTT assays. Platelet aggregation studies use platelet-rich plasma from human or animal blood. All experiments include vehicle controls and reference compounds.
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| Animal Protocol |
In vivo animal studies with 3',4'-Dihydroxyacetophenone are conducted in rodent models for cardiovascular research and inflammation studies. The compound is administered via intraperitoneal or oral gavage at doses ranging from 5-100 mg/kg. Anti-arrhythmia activity is assessed in models of induced arrhythmia (e.g., aconitine-induced arrhythmia in rats). Anti-inflammatory effects are evaluated in models of acute inflammation (e.g., carrageenan-induced paw edema). Platelet aggregation and thrombosis models may also be used. Each group consists of 6-10 animals with appropriate vehicle and positive controls.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of 3',4'-Dihydroxyacetophenone have not been extensively characterized. As a small, polar phenolic compound (MW 152.15), it is expected to have moderate oral bioavailability with rapid absorption from the gastrointestinal tract. The compound likely undergoes extensive first-pass metabolism, primarily through glucuronidation and sulfation of the hydroxyl groups. Distribution is expected to be widespread due to its lipophilic acetophenone moiety. Elimination occurs via renal excretion of conjugated metabolites. Detailed PK studies are needed for comprehensive characterization.
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| Toxicity/Toxicokinetics |
Toxicological data for 3',4'-Dihydroxyacetophenone indicate that it is generally considered safe at research doses. No significant acute toxicity has been reported. The compound is a natural product found in medicinal herbs, suggesting a favorable safety profile. However, comprehensive toxicological studies, including chronic toxicity, genotoxicity, and reproductive toxicity, have not been conducted. As with all research chemicals, appropriate safety precautions should be taken during handling, and the compound should be used only for research purposes.
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| References | |
| Additional Infomation |
3,4-Dihydroxyacetophenone is a type of acetophenone compound and is a metabolite. It has been reported to be found in ovate spruce, grey spruce, and other organisms with relevant data.
3',4'-Dihydroxyacetophenone is a natural bioactive compound with multiple pharmacological activities, including tyrosinase inhibition, antioxidant, anti-inflammatory, and anti-arrhythmia effects. It is used in research on pigmentation disorders, cardiovascular diseases, and inflammation. The compound is also utilized in analytical method development and quality control applications for pharmaceutical analysis. It serves as an intermediate in the commercial production of norepinephrine. Not approved for clinical therapeutic use; intended for research purposes 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 # |
1197-09-7
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| PubChem CID |
14530
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| Appearance |
Light brown to brown solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
372.4±27.0 °C at 760 mmHg
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| Melting Point |
117 °C
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| Flash Point |
193.2±20.2 °C
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| Vapour Pressure |
0.0±0.9 mmHg at 25°C
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| Index of Refraction |
1.595
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| LogP |
1.28
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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 |
11
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| Complexity |
155
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
UCQUAMAQHHEXGD-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C8H8O3/c1-5(9)6-2-3-7(10)8(11)4-6/h2-4,10-11H,1H3
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| Chemical Name |
1-(3,4-dihydroxyphenyl)ethanone
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| Synonyms |
3',4'Dihydroxyacetophenone; 3',4' Dihydroxyacetophenone
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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 (~328.62 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (16.43 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 (16.43 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 (16.43 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 | 6.5725 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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