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| 25g |
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| Targets |
The primary biological target and mechanism of action of 5-Acetylsalicylic acid are not as clearly defined as those of its more famous relative, aspirin. While it is recognized for its anti-inflammatory effects, particularly in the context of inflammatory bowel disease (IBD), its specific molecular target is not fully characterized. It is believed to exert its effects through the modulation of inflammatory pathways, potentially by inhibiting the synthesis of pro-inflammatory prostaglandins, similar to other salicylates. However, unlike aspirin, which irreversibly inhibits cyclooxygenase (COX) enzymes, 5-Acetylsalicylic acid may have a different or additional mechanism of action. Its activity in IBD models suggests it may act locally in the gastrointestinal tract to reduce inflammation. It is also considered a bioactive compound with potential effects beyond simple COX inhibition, possibly involving the modulation of transcription factors like NF-κB. Research into its precise mechanism is ongoing.
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| ln Vitro |
The in vitro activity of 5-Acetylsalicylic acid is not as extensively characterized as that of many drug candidates, but it is recognized for its anti-inflammatory properties. In cell-based models of inflammation, such as macrophages stimulated with lipopolysaccharide (LPS), the compound has been shown to reduce the production of pro-inflammatory cytokines like TNF-α and IL-6. Its activity is often compared to that of other salicylates. The compound's physicochemical properties, such as its solubility and stability, are well-defined. It is soluble in DMSO (75 mg/mL), which is a key parameter for preparing stock solutions for in vitro experiments. As an organic acid, its pKa is 2.62±0.10, indicating that it is largely ionized at physiological pH, which may influence its cell permeability and oral bioavailability.
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| ln Vivo |
In vivo, 5-Acetylsalicylic acid is being investigated for its therapeutic potential in treating inflammatory bowel disease (IBD). Its anti-inflammatory properties are believed to be beneficial in managing the chronic inflammation associated with conditions like ulcerative colitis and Crohn's disease. While it is not as widely used as mesalamine or other standard IBD therapies, it is considered an active agent in this context. The compound is typically administered orally, and its effects are thought to be localized in the gastrointestinal tract. Its use in research models of colitis has shown promise in reducing inflammation and tissue damage. The compound is also an organic intermediate, indicating that it may serve as a precursor for the synthesis of other, more complex molecules with therapeutic potential.
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| Enzyme Assay |
In vitro enzyme assays for 5-Acetylsalicylic acid are not standard, as its primary mechanism is not the inhibition of a single enzyme like COX. However, its anti-inflammatory activity can be assessed using biochemical assays that measure the production of inflammatory mediators. For example, COX-1 and COX-2 enzyme activity assays could be performed to determine if the compound inhibits these enzymes. In such an assay, the compound would be incubated with the enzyme and a substrate, and the production of prostaglandin would be measured. Its effects could be compared to a known inhibitor like aspirin or ibuprofen. However, given its potential mechanism, other assays, such as those measuring NF-κB activation or cytokine production in cell lysates, may be more relevant for characterizing its activity. These biochemical assays help to dissect the compound's mode of action.
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| Cell Assay |
In vitro cell-based assays are used to evaluate the anti-inflammatory activity of 5-Acetylsalicylic acid. A common model is the LPS-stimulated macrophage assay. In this assay, a macrophage cell line like RAW 264.7 is pre-treated with varying concentrations of the compound for 1-2 hours and then stimulated with LPS (e.g., 1 μg/mL) for 24 hours. After stimulation, the culture supernatant is collected, and the levels of pro-inflammatory cytokines such as TNF-α, IL-1β, and IL-6 are measured using an enzyme-linked immunosorbent assay (ELISA). The compound's ability to inhibit the production of these cytokines is a measure of its anti-inflammatory activity. Cell viability is also assessed to ensure that the observed effects are not due to cytotoxicity. These assays provide a functional readout of the compound's activity in a cellular context and are essential for studying its mechanism of action.
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| Animal Protocol |
In vivo animal studies for 5-Acetylsalicylic acid are likely focused on models of inflammatory bowel disease (IBD). A common model is the dextran sulfate sodium (DSS)-induced colitis model in mice. In this model, mice are given DSS in their drinking water to induce acute colitis, which mimics the symptoms of human IBD. The test compound, 5-Acetylsalicylic acid, is typically administered orally by gavage daily. Disease severity is assessed by monitoring body weight, stool consistency, and the presence of fecal blood (clinical score). After the study period, the animals are euthanized, and the colons are collected for histological analysis to evaluate the degree of inflammation and tissue damage. The levels of inflammatory markers in the colonic tissue can also be measured. This model is widely used to assess the efficacy of potential anti-inflammatory agents for IBD.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of 5-Acetylsalicylic acid are not extensively documented, but they can be inferred from its physicochemical properties. As a small, moderately lipophilic molecule with a pKa of 2.62, it is expected to be absorbed from the gastrointestinal tract after oral administration. However, its solubility in water is likely limited, and its bioavailability may be influenced by food and gastric pH. It is metabolized in the liver and excreted renally. The compound's use as an organic intermediate suggests that it may be metabolized or conjugated to more water-soluble forms for elimination. For research purposes, it is typically stored as a powder at -20°C or 4°C and is soluble in DMSO at 75 mg/mL. These properties are important for formulating the compound for in vivo studies.
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| Toxicity/Toxicokinetics |
The toxicological profile of 5-Acetylsalicylic acid has not been extensively detailed in standard literature, but it is expected to be similar to other salicylates. At therapeutic doses, it is generally well-tolerated. Potential side effects may include gastrointestinal irritation, which is common for salicylate compounds. At high doses, it could cause more significant toxicity, including metabolic acidosis, central nervous system effects, and liver toxicity. For research purposes, standard laboratory safety practices should be observed when handling the compound. This includes wearing gloves and safety goggles to avoid skin contact and inhalation of the powder. It is intended for research use only and is not for human therapeutic or diagnostic use.
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| Additional Infomation |
5-Acetylsalicylic acid is an aromatic ketone.
5-Acetylsalicylic acid is also known by the synonyms 5-acetyl-2-hydroxybenzoic acid and has the UNII code T75Z3S63DL. It is structurally related to aspirin (2-acetoxybenzoic acid) but differs in the position of the acetyl group, which significantly alters its biological activity. While aspirin is a well-known pain reliever and anti-inflammatory agent, 5-Acetylsalicylic acid is being investigated specifically for its potential in treating inflammatory bowel disease. Its role as an organic intermediate means it is a valuable building block for synthesizing other complex molecules in medicinal chemistry. The compound is available from chemical suppliers and is intended for research use only. It is a white to pale yellow crystalline solid and should be stored in a dry, dark place at 2-8°C to maintain its stability. |
| Molecular Formula |
C9H8O4
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|---|---|
| Molecular Weight |
180.15742
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| Exact Mass |
180.042
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| CAS # |
13110-96-8
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| PubChem CID |
83151
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.365 g/cm3
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| Boiling Point |
413ºC at 760 mmHg
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| Melting Point |
214-216°C
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| Flash Point |
250°C
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| Vapour Pressure |
1.46E-07mmHg at 25°C
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| LogP |
1.293
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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 |
2
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| Heavy Atom Count |
13
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| Complexity |
224
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC(=O)C1=CC(=C(C=C1)O)C(=O)O
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| InChi Key |
NZRDKNBIPVLNHA-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H8O4/c1-5(10)6-2-3-8(11)7(4-6)9(12)13/h2-4,11H,1H3,(H,12,13)
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| Chemical Name |
5-acetyl-2-hydroxybenzoic acid
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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 (~555.06 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (13.88 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 (13.88 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 (13.88 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 | 5.5506 mL | 27.7531 mL | 55.5062 mL | |
| 5 mM | 1.1101 mL | 5.5506 mL | 11.1012 mL | |
| 10 mM | 0.5551 mL | 2.7753 mL | 5.5506 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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