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| Targets |
4-Hydroxyacetophenone does not have a specific pharmacological target, as it is primarily a chemical intermediate and reagent. However, its phenolic structure allows it to act as a free radical scavenger, contributing to antioxidant effects. It may inhibit enzymes such as cyclooxygenase (COX) and lipoxygenase, suggesting anti-inflammatory potential. The compound also shows weak antimicrobial activity against certain bacteria and fungi. As a metabolic intermediate, it can be converted to hydroxyphenylacetic acid or other derivatives in biological systems. Its interactions with metal ions (e.g., ferric) enable its use as a chelating agent in analytical chemistry.
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| ln Vitro |
In vitro, 4-Hydroxyacetophenone exhibits moderate antioxidant activity measured by DPPH radical scavenging, ABTS, and FRAP assays. It shows dose-dependent free radical neutralization with IC₅₀ values typically in the 100–500 µM range. Anti-inflammatory effects have been observed in macrophage cell lines (e.g., RAW 264.7) where it reduces LPS-induced nitric oxide and TNF-α production. It also inhibits COX-2 expression at concentrations of 25–100 µM. Antimicrobial activity is weak to moderate, with minimum inhibitory concentrations (MICs) against Staphylococcus aureus and Escherichia coli in the millimolar range. The compound is not significantly cytotoxic to normal cells at concentrations up to 500 µM.
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| ln Vivo |
In vivo, 4-Hydroxyacetophenone has been studied for its anti-inflammatory and hepatoprotective effects in rodent models. In carrageenan-induced paw edema models, oral administration of 50–200 mg/kg reduces swelling dose‑dependently. It also protects against CCl₄-induced liver injury by decreasing serum transaminases and lipid peroxidation, likely due to its antioxidant properties. The compound is rapidly metabolized to conjugated metabolites (glucuronides, sulfates) and excreted in urine. Its bioavailability is moderate due to first‑pass metabolism. It is used as a reference compound in studies of phenolic acid pharmacokinetics. No significant adverse effects were reported at doses up to 300 mg/kg in acute toxicity studies.
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| Enzyme Assay |
In vitro enzyme/receptor binding (non-cellular) assays for 4-Hydroxyacetophenone typically involve measuring antioxidant capacity via DPPH radical scavenging: the compound is incubated with DPPH (0.1 mM) in methanol or ethanol, and absorbance at 517 nm is measured after 30 minutes. IC₅₀ is calculated. For metal chelation, ferrozine assay is used with Fe²⁺ to measure chelating activity. Enzyme inhibition (COX-1/2, LOX) can be assessed using purified enzymes with colorimetric or fluorometric substrates. The compound may be used as a standard in HPLC for the quantification of phenolic compounds. These assays characterize its chemical reactivity and potential biological activities without cellular interference.
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| Cell Assay |
In vitro cellular experiments with 4-Hydroxyacetophenone are performed using macrophage cells (RAW 264.7) or hepatocytes (HepG2). Cells are cultured in DMEM with 10% FBS and treated with varying concentrations (10–500 µM) of the compound for 24 hours. Anti-inflammatory activity is induced by LPS (1 µg/mL); nitric oxide production is measured by Griess assay, and cytokines (TNF-α, IL-6) by ELISA. Cell viability is assessed by MTT to ensure non-cytotoxicity. For antioxidant studies, cells are exposed to H₂O₂ or CCl₄, and reactive oxygen species are measured using DCFH-DA. The compound reduces oxidative stress markers dose-dependently. Cells are maintained at 37°C in 5% CO₂.
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| Animal Protocol |
In vivo animal studies with 4-Hydroxyacetophenone have been conducted in rodent models of inflammation and hepatotoxicity. For inflammation, rats are given oral doses (50, 100, 200 mg/kg) one hour before carrageenan injection into the hind paw; paw volume is measured plethysmographically at intervals. For hepatoprotection, mice are treated with CCl₄ (0.1 mL/kg) after 7 days of compound administration; serum ALT, AST, and hepatic MDA and GSH are measured. Histopathology of liver sections is evaluated. Pharmacokinetics are studied after oral or i.v. dosing; blood and urine samples are analyzed by HPLC for parent compound and metabolites. The compound shows dose-dependent effects with good tolerance.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
Known human metabolites of 4-hydroxyacetophenone include (2S,3S,4S,5R)-6-(4-acetylphenoxy)-3,4,5-trihydroxyoxacyclohexane-2-carboxylic acid. Pharmacokinetic properties of 4-Hydroxyacetophenone indicate rapid absorption after oral administration with Tmax ~0.5‑1 h in rats. The compound has a half‑life of about 2‑3 hours due to extensive metabolism by sulfation and glucuronidation. Bioavailability is ~30‑40% due to first‑pass metabolism. It distributes widely to liver, kidney, and plasma, with low brain penetration. Excretion is primarily renal as conjugates. Molecular weight 136.15, solubility in water ~10 mg/mL, logP ~1.5. Storage: 2‑8°C, protected from light. The compound is stable under normal conditions. Purity: ≥99%. |
| Toxicity/Toxicokinetics |
4-Hydroxyacetophenone is generally recognized as safe (GRAS) for use as a flavoring agent in food. Acute toxicity is low (oral LD₅₀ in rats > 2000 mg/kg). Skin and eye irritation may occur at high concentrations; it is not mutagenic in Ames tests. Chronic exposure studies are lacking, but it is not classified as a carcinogen. Standard safety precautions include wearing gloves and goggles, working in a fume hood, and avoiding inhalation of dust. The compound is for research use and not for human therapeutic use without further evaluation. Purity: ≥99%. Storage: 2‑8°C, protect from light.
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| References |
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| Additional Infomation |
4'-Hydroxyacetophenone is a monohydroxyacetophenone with a hydroxyl substituent at the 4' position. It can be used as a plant metabolite, a fungal metabolite, and a mouse metabolite. It has been reported to exist in Cytospora ceratosperma, Haploappus arbutoides, and other organisms with relevant data.
4-Hydroxyacetophenone (CAS 99‑93‑4) is a phenolic ketone with molecular formula C₈H₈O₂ and molecular weight 136.15 g/mol. It is a white crystalline powder used as a building block in organic synthesis, a precursor for pharmaceuticals (e.g., acetaminophen analogues), and a reagent in analytical chemistry. It exhibits antioxidant, anti‑inflammatory, and weak antimicrobial activities. It is also used as a polymerization inhibitor and as a flavoring agent. Purity: ≥99%. Storage: 2‑8°C, protect from light. |
| Molecular Formula |
C₈H₈O₂
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|---|---|
| Molecular Weight |
136.15
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| Exact Mass |
136.052
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| CAS # |
99-93-4
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| PubChem CID |
7469
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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 |
313.0±0.0 °C at 760 mmHg
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| Melting Point |
132-135 °C(lit.)
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| Flash Point |
121.2±12.4 °C
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| Vapour Pressure |
0.0±0.7 mmHg at 25°C
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| Index of Refraction |
1.552
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| LogP |
1.42
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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 |
1
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| Heavy Atom Count |
10
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| Complexity |
123
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
TXFPEBPIARQUIG-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C8H8O2/c1-6(9)7-2-4-8(10)5-3-7/h2-5,10H,1H3
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| Chemical Name |
1-(4-hydroxyphenyl)ethanone
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| Synonyms |
4Hydroxyacetophenone; 4 Hydroxyacetophenone
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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 (~734.48 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (18.36 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 (18.36 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 (18.36 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 | 7.3448 mL | 36.7242 mL | 73.4484 mL | |
| 5 mM | 1.4690 mL | 7.3448 mL | 14.6897 mL | |
| 10 mM | 0.7345 mL | 3.6724 mL | 7.3448 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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