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| Other Sizes |
| Targets |
4-Nitrocatechol targets lipoxygenase, an enzyme involved in the metabolism of arachidonic acid to leukotrienes, which are important mediators of inflammation. By inhibiting lipoxygenase, 4-nitrocatechol can modulate inflammatory responses. The compound is also a xenobiotic metabolite in humans and serves as a metabolic marker for functional cytochrome P450 2E1 in mammalian cell microsomes. It has been characterized as an alternative substrate for various enzymes.
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| ln Vitro |
4-Nitrocatechol is a potent lipoxygenase inhibitor. As a catechol compound, it may also exhibit antioxidant properties. The compound is a byproduct of the hydroxylation of p-nitrophenol by CYP2E1 and serves as a metabolic marker for this enzyme. 4-Nitrocatechol has been reported to be present in Homo sapiens. Its biological activity is primarily studied in the context of metabolism and enzyme inhibition.
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| ln Vivo |
In vivo activity data for 4-nitrocatechol are limited. As a human xenobiotic metabolite, it is formed in the body from the metabolism of p-nitrophenol by CYP2E1. The compound is not used as a therapeutic agent but is studied as a metabolic marker. Its presence in the body reflects exposure to p-nitrophenol or other nitroaromatic compounds. Specific in vivo efficacy studies are not applicable.
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| Enzyme Assay |
The in vitro enzyme assay for 4-nitrocatechol typically involves measuring the inhibition of lipoxygenase activity. Lipoxygenase enzyme is incubated with varying concentrations of 4-nitrocatechol (typically 0.1-100 µM) in the presence of a substrate such as arachidonic acid or linoleic acid. The enzymatic activity is measured by monitoring the formation of hydroperoxy fatty acids spectrophotometrically or by using fluorescent probes. The IC50 value is determined by plotting the percentage of inhibition against compound concentration.
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| Cell Assay |
In vitro cellular assays for 4-nitrocatechol are not typical, as the compound is primarily studied as an enzyme inhibitor and metabolite. For metabolic studies, cells expressing CYP2E1 are incubated with p-nitrophenol, and the formation of 4-nitrocatechol is measured by HPLC or LC-MS. The compound can also be used to assess lipoxygenase activity in cell lysates. The compound is dissolved in DMSO or ethanol and diluted in assay buffer.
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| Animal Protocol |
In vivo animal studies for 4-nitrocatechol are not typically performed for therapeutic purposes. The compound may be used in toxicological studies to assess exposure to nitroaromatic compounds. The compound is administered to animals, and blood, urine, and tissue samples are collected for metabolic analysis. The compound is not intended for human therapeutic use.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
4-Nitrocatechol (4NC) is a known human metabolite of 4-nitrophenol. 4-Nitrocatechol has a molecular weight of 155.11 g/mol and formula C6H5NO4. It appears as a light brown to yellow solid powder with a density of 1.6±0.1 g/cm³, melting point of 173-177°C, and boiling point of 358.2°C. LogP is 1.68. It is soluble in DMSO (~100 mg/mL). Recommended storage is powder at -20°C for 3 years. The compound is a C-nitro compound belonging to the catechol class. |
| Toxicity/Toxicokinetics |
4-Nitrocatechol is intended for research use only and is not approved for human therapeutic applications. As a nitroaromatic compound, appropriate safety precautions should be taken when handling. Standard toxicity assessments would include acute toxicity, genotoxicity, and repeated-dose toxicity studies. The compound is a human xenobiotic metabolite and a lipoxygenase inhibitor.
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| References | |
| Additional Infomation |
4-Nitrocatechol belongs to the catechol class of compounds and is a compound in which a nitro group is substituted at the 4-position of phenyl-1,2-diol. It is a byproduct of the hydroxylation of p-nitrophenol. It is a lipoxygenase inhibitor and a xenobiotic metabolite in humans. It is a C-nitro compound belonging to the catechol class. It is the conjugate acid of 2-hydroxy-4-nitrophenol salt. There are reports and relevant data regarding the presence of 4-nitrocatechol in Homo sapiens.
4-Nitrocatechol (CAS 3316-09-4) is a nitroaromatic compound belonging to the catechol class. It has a molecular weight of 155.11 g/mol and formula C6H5NO4. 4-Nitrocatechol is a potent lipoxygenase inhibitor and a human xenobiotic metabolite formed by hydroxylation of p-nitrophenol by CYP2E1. It is also known as 4-nitrobenzene-1,2-diol and 4-nitropyrocatechol. The compound is not approved for clinical use. |
| Molecular Formula |
C6H5NO4
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| Molecular Weight |
155.1082
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| Exact Mass |
155.021
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| CAS # |
3316-09-4
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| PubChem CID |
3505109
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| Appearance |
Light brown to yellow solid powder
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| Density |
1.6±0.1 g/cm3
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| Boiling Point |
358.2±32.0 °C at 760 mmHg
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| Melting Point |
173-177 °C(lit.)
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| Flash Point |
168.8±13.6 °C
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| Vapour Pressure |
0.0±0.8 mmHg at 25°C
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| Index of Refraction |
1.668
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| LogP |
1.68
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
0
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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 |
XJNPNXSISMKQEX-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C6H5NO4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H
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| Chemical Name |
4-nitrobenzene-1,2-diol
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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 (~644.70 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (16.12 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 (16.12 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.4470 mL | 32.2352 mL | 64.4704 mL | |
| 5 mM | 1.2894 mL | 6.4470 mL | 12.8941 mL | |
| 10 mM | 0.6447 mL | 3.2235 mL | 6.4470 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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