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| Targets |
N-(4-Formylphenyl)acetamide does not have a well-defined primary biological target as it is a research intermediate rather than a drug. However, it has been evaluated for activity against cAMP phosphodiesterase (PDE) using bovine aorta enzyme preparations, where it exhibited insignificant inhibitory activity at 1 uM cGMP in the presence of calcium (10 uM) and calmodulin (15 nM). The compound is used as a building block for the synthesis of formyl peptide receptor (FPR) ligands. FPRs are G protein-coupled receptors involved in the chemotaxis of polymorphonuclear leukocytes (PMNs) in response to bacterial peptides and mitochondrial N-formyl peptides, playing a role in inflammation and infection. The aldehyde group can form Schiff bases with primary amines, allowing the compound to serve as a starting point for the construction of more complex molecules targeting formyl peptide receptors. No other specific receptor or enzyme targets have been definitively characterized for the parent compound.
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| ln Vitro |
The in vitro activity of N-(4-Formylphenyl)acetamide has been characterized in enzyme inhibition assays. It was tested for its ability to inhibit cAMP phosphodiesterase (PDE) in an in vitro cell-free system using bovine aorta as the enzyme source. The assay conditions included 1 uM cGMP in the presence of calcium (10 uM) and calmodulin (15 nM). Under these conditions, the compound was found to be insignificant as an inhibitor, indicating that it does not substantially affect the degradation of cAMP by PDE. Beyond this single assay, no other in vitro biological activities have been reported for the parent compound. It is important to note that the compound is a synthetic building block and its biological activity is typically assessed only as part of the characterization of the final synthesized molecules, not the intermediate itself. Therefore, most of its in vitro applications are chemical rather than pharmacological.
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| ln Vivo |
No dedicated in vivo studies have been published for N-(4-Formylphenyl)acetamide as a therapeutic agent. The compound is a synthetic intermediate and not a drug candidate. It has not been tested in animal models for efficacy against any disease. Its in vivo relevance is derived entirely from its use as a precursor for the synthesis of formyl peptide receptor (FPR) ligands and other bioactive molecules that may be evaluated in vivo. For example, FPR agonists and antagonists synthesized from this building block have been studied in animal models of inflammation, infection, and cancer. However, the parent compound itself has not been administered to animals for efficacy testing. Any in vivo exposure would be limited to toxicological or metabolic studies of the compound as a chemical intermediate. No pharmacokinetic or pharmacodynamic data are available for this compound.
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| Enzyme Assay |
The cell-free assay for N-(4-Formylphenyl)acetamide evaluating cAMP phosphodiesterase (PDE) inhibition was performed as follows: (1) Prepare bovine aorta tissue homogenate as a source of cAMP PDE enzyme. (2) Prepare assay buffer: 40 mM Tris-HCl, pH 8.0, containing 5 mM MgCl2, 0.1% bovine serum albumin (BSA), and 0.1 mM EGTA. (3) Prepare a reaction mixture containing 1 uM cGMP (as an allosteric activator), 10 uM calcium chloride, and 15 nM calmodulin (CaM) to activate the Ca2+/CaM-dependent PDE. (4) Add varying concentrations of N-(4-Formylphenyl)acetamide (0.1-100 uM) dissolved in DMSO (final DMSO concentration ≤1%). (5) Add the bovine aorta PDE enzyme preparation to initiate the reaction. (6) Incubate at 30degC for 15-30 minutes. (7) Stop the reaction by boiling for 2-3 minutes or by adding 0.1 M HCl. (8) Quantify the amount of cAMP remaining or the amount of 5′-AMP produced using a commercial cAMP-Glo™ assay or a two-step enzymatic method (e.g., snake venom 5′-nucleotidase treatment followed by phosphate determination). (9) In this assay, N-(4-Formylphenyl)acetamide was found to be an insignificant inhibitor, indicating that it does not substantially affect PDE activity.
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| Cell Assay |
No specific cellular assay protocols are available for N-(4-Formylphenyl)acetamide itself as a test compound, as it is a chemical intermediate rather than a biologically active molecule. However, the compound can be evaluated for general cytotoxicity in standard cell culture models to determine its safety profile as a reagent. A generic protocol: (1) Culture adherent human cell lines (e.g., HEK-293 or HeLa) in DMEM with 10% FBS and 1% penicillin/streptomycin at 37degC in 5% CO2. (2) Seed cells into 96-well plates at a density of 5,000-10,000 cells/well and allow to attach overnight. (3) Prepare a 100 mM stock solution of N-(4-Formylphenyl)acetamide in DMSO. (4) Dilute the stock in cell culture medium to achieve final concentrations ranging from 1 uM to 1 mM, with a final DMSO concentration ≤0.5%. (5) Treat cells for 24-72 hours. (6) Assess cell viability using the MTT assay: add 20 uL of 5 mg/mL MTT per well, incubate 4 hours at 37degC, remove medium, add 150 uL DMSO to dissolve formazan crystals, and read absorbance at 570 nm. (7) Alternatively, use the CellTiter-Glo luminescent assay for ATP quantification. (8) For assessment of apoptosis, stain cells with annexin V-FITC and propidium iodide (PI) and analyze by flow cytometry. (9) The compound is expected to have low to moderate cytotoxicity due to the presence of both aldehyde and amide functional groups, which could potentially react with cellular proteins. However, specific IC₅0 values have not been reported.
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| Animal Protocol |
No in vivo animal study protocols have been established for N-(4-Formylphenyl)acetamide as a test article, because it is a synthetic intermediate and not intended for therapeutic use. Should an acute toxicity study be required for safety assessment, a generic protocol following OECD Guideline 423 is suggested: (1) Fast female Sprague-Dawley rats (8-12 weeks old, 180-220 g) overnight with free access to water. (2) Prepare N-(4-Formylphenyl)acetamide as a suspension in 0.5% carboxymethylcellulose (CMC) or a solution in a minimal amount of DMSO diluted in corn oil (final DMSO ≤5%). (3) Administer a single dose by oral gavage at levels of 300, 1000, or 2000 mg/kg (n=3-5 per dose). (4) Observe animals continuously for the first 4 hours and then daily for 14 days for signs of acute toxicity (tremors, convulsions, lethargy, diarrhea, labored breathing, changes in behavior). (5) Record body weights daily. (6) At the end of the observation period, euthanize animals by CO2 asphyxiation and perform gross necropsy, examining the gastrointestinal tract, liver, kidneys, spleen, heart, and lungs. (7) Preserve any grossly abnormal tissues in 10% formalin for histopathological examination. (8) Calculate the LD₅0 using the up-and-down method or Probit analysis. No toxicity data are available for this specific compound, so extrapolation from structurally related compounds (such as acetamidobenzaldehyde derivatives) may be necessary.
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| ADME/Pharmacokinetics |
No pharmacokinetic data are available for N-(4-Formylphenyl)acetamide. The molecular weight is 163.17, and the compound is a solid powder at room temperature with a melting point in the range of 150-155degC. The compound contains an aldehyde group and an amide group; therefore, it is likely to be reasonably stable in dry form but may undergo oxidation or hydrolysis in the presence of moisture or light. For storage, the powder should be kept at -20degC in a tightly sealed container, protected from light and moisture. Under these conditions, it is stable for up to three years. For experimental use, it is soluble in organic solvents such as DMSO (≥25 mg/mL, ~153 mM), ethanol, and methanol, but has limited water solubility due to the hydrophobic phenyl ring. Stock solutions in DMSO can be stored at -80degC for up to 6 months or at -20degC for up to 1 month; repeated freeze-thaw cycles should be avoided. No information is available regarding plasma protein binding, volume of distribution, half-life, or metabolic clearance.
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| Toxicity/Toxicokinetics |
Specific toxicological data for N-(4-Formylphenyl)acetamide are not available in the literature. As with all chemical reagents, appropriate safety precautions should be taken: avoid skin and eye contact, avoid inhalation of dust or vapors, and avoid ingestion. The compound is not intended for human consumption and has not undergone formal toxicological assessment for carcinogenicity, genotoxicity, or reproductive toxicity. The aldehyde group may cause irritation to mucous membranes, skin, and eyes. Aldehydes can be protein-reactive and may have sensitization potential. Standard laboratory safety practices, including wearing appropriate personal protective equipment (gloves, lab coat, safety goggles), working in a well-ventilated area (fume hood), and washing hands thoroughly after handling, should be followed. Spills should be cleaned up promptly using appropriate absorbent materials. The compound is for research use only and should be disposed of according to local regulations for chemical waste. No clinical or human toxicity data are available.
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| References | |
| Additional Infomation |
4-Acetamidobenzaldehyde is an aniline compound, belonging to the acetamide class of compounds.
N-(4-Formylphenyl)acetamide (CAS 122-85-0) is also known as 4-acetamidobenzaldehyde or p-acetamidobenzaldehyde. It is a key intermediate in the synthesis of Schiff bases, heterocyclic compounds (such as quinazolines, thiazolidinones, and pyrazoles), and other medicinally relevant molecules. The aldehyde group allows for condensation reactions with primary amines to form imines (Schiff bases), which are important pharmacophores in many bioactive compounds. The acetylamino group can be deprotected to yield the corresponding amine, providing additional synthetic versatility. In medicinal chemistry research, this compound is used as a building block for the synthesis of formyl peptide receptor (FPR) ligands, which are studied for their role in modulating the immune response to bacterial infection and in inflammation. FPR-1-mediated chemotactic response of polymorphonuclear leukocytes (PMNs) to bacterial peptides is a key part of the innate immune response. The compound is commercially available at purities of 98-99% (HPLC) and is typically sold as a solid powder. It is not an FDA-approved drug, has no clinical trial history, and is strictly a research chemical for laboratory use. |
| Molecular Formula |
C9H9NO2
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|---|---|
| Molecular Weight |
163.17
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| Exact Mass |
163.063
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| CAS # |
122-85-0
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| PubChem CID |
73942
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| Appearance |
Solid powder ; White to yellow
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
384.3±25.0 °C at 760 mmHg
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| Melting Point |
148-153 °C(lit.)
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| Flash Point |
181.8±23.3 °C
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| Vapour Pressure |
0.0±0.9 mmHg at 25°C
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| Index of Refraction |
1.622
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| LogP |
1.25
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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 |
2
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| Heavy Atom Count |
12
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| Complexity |
171
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC(=O)NC1=CC=C(C=C1)C=O
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| InChi Key |
SKLUWKYNZNXSLX-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H9NO2/c1-7(12)10-9-4-2-8(6-11)3-5-9/h2-6H,1H3,(H,10,12)
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| Chemical Name |
N-(4-formylphenyl)acetamide
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| Synonyms |
4-Acetamidobenzaldehyde
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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: (1). 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 | 6.1286 mL | 30.6429 mL | 61.2858 mL | |
| 5 mM | 1.2257 mL | 6.1286 mL | 12.2572 mL | |
| 10 mM | 0.6129 mL | 3.0643 mL | 6.1286 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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