| Size | Price | Stock | Qty |
|---|---|---|---|
| 250mg |
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| 500mg |
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| Other Sizes |
| Targets |
Cyclooxygenase-2 (COX-2) and Hepatic N-Acetyltransferase 2 (NAT2). 4-Hydroxyacetophenone oxime is a weak inhibitor of these enzymes. As an impurity of acetaminophen, it may interfere with the arachidonic acid pathway by inhibiting COX-2 and also affect phase II drug metabolism by inhibiting NAT2. It exhibits antifungal, antibacterial, and anticancer properties in vitro and in vivo.
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| ln Vitro |
The compound has been reported to demonstrate antifungal activity surpassing the efficacy of commercial agents like clotrimazole and miconazole. It also exhibits antibacterial effects against various pathogens and antiproliferative effects in cancer cell lines, although the exact IC50 values vary widely depending on the assay system and cell type used.
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| ln Vivo |
Acetaminophen itself acts as a potent antipyretic and analgesic by inhibiting COX-2 in the CNS. While the parent drug has low anti-inflammatory activity peripherally, 4-Hydroxyacetophenone oxime, as an impurity, is not considered to contribute significantly to the therapeutic effects of acetaminophen at standard doses and is primarily monitored for safety and regulatory compliance.
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| Enzyme Assay |
Cell-free COX-2 inhibition assays: Purified human COX-2 enzyme (0.1-0.5 U) is incubated in 100 mM Tris-HCl buffer (pH 8.0) containing 5 microM hematin, 2 mM phenol, and varying concentrations of 4-Hydroxyacetophenone oxime (1-1000 microM). The reaction is initiated by adding arachidonic acid (100 microM), followed by incubation for 2 min at 37degC. Prostaglandin (PGE2) production is quantified using an enzyme immunoassay (EIA) kit, and IC50 values are calculated.
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| Cell Assay |
Not applicable (no validated cell-based assay specific to this impurity). In cytotoxicity screening, human hepatocytes (HepaRG) are seeded in 96-well plates and treated with 4-Hydroxyacetophenone oxime (0.1-1000 microM) for 24-72 h. Cell viability is assessed using MTT or CellTiter-Glo assays. Alternatively, antifungal activity is tested against Candida albicans cultures in RPMI-1640 medium, with MIC determination after 48 h incubation at 35degC.
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| Animal Protocol |
Not applicable (impurity standard, not evaluated in dedicated animal efficacy studies). For general toxicity testing, male Sprague-Dawley rats (200-250 g) are dosed orally with 4-Hydroxyacetophenone oxime (50-500 mg/kg) or vehicle for 14 days. Body weight, food consumption, serum biochemistry (ALT, AST, creatinine, BUN), and histopathology (liver, kidney) are assessed to determine the no-observed-adverse-effect level (NOAEL).
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| ADME/Pharmacokinetics |
4-Hydroxyacetophenone oxime is a small molecule with moderate lipophilicity. As an impurity, it is typically present at levels <0.1% in pharmaceutical-grade paracetamol. The compound is primarily excreted in urine after conjugation. Detailed human pharmacokinetic (PK) data is not available; its detection and quantification are performed using HPLC-UV or LC-MS methods for quality control.
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| References | |
| Additional Infomation |
Acetaminophen was FDA-approved in 1951 as a non-prescription analgesic/antipyretic. The oxime derivative is strictly a research tool. Its primary application is as an analytical reference standard in pharmaceutical quality control (QC), and it is listed in pharmacopeias as a specified impurity to be monitored and controlled during paracetamol drug substance manufacturing.
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| Molecular Formula |
C₈H₉NO₂
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|---|---|
| Molecular Weight |
151.16
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| Exact Mass |
151.063
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| CAS # |
34523-34-7
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| PubChem CID |
135502776
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| Appearance |
White to off-white solid powder
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| Density |
1.246g/cm3
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| Boiling Point |
294.8ºC at 760mmHg
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| Melting Point |
143 °C
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| Flash Point |
132.1ºC
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| Index of Refraction |
1.591
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| LogP |
1.59
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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 |
148
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C/C(=N\O)/C1=CC=C(C=C1)O
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| InChi Key |
BVZSQTRWIYKUSF-RMKNXTFCSA-N
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| InChi Code |
InChI=1S/C8H9NO2/c1-6(9-11)7-2-4-8(10)5-3-7/h2-5,10-11H,1H3/b9-6+
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| Chemical Name |
4-[(E)-N-hydroxy-C-methylcarbonimidoyl]phenol
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| Synonyms |
4Hydroxyacetophenone oxime; 4 Hydroxyacetophenone oxime
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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 Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| 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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.6155 mL | 33.0775 mL | 66.1551 mL | |
| 5 mM | 1.3231 mL | 6.6155 mL | 13.2310 mL | |
| 10 mM | 0.6616 mL | 3.3078 mL | 6.6155 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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