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| Targets |
p-Anisic acid does not have a specific pharmacological target. Its antimicrobial activity is attributed to its ability to disrupt microbial cell membranes and inhibit cell wall synthesis. It acts as a weak acid that can penetrate the cell membrane and acidify the cytoplasm, leading to growth inhibition. Its antioxidant properties are due to its ability to scavenge free radicals and chelate metal ions. Anti-inflammatory effects may involve inhibition of prostaglandin synthesis and modulation of cytokine production.
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| ln Vitro |
In vitro, p-anisic acid exhibits antimicrobial activity against a broad spectrum of bacteria, including Escherichia coli, Staphylococcus aureus, and Salmonella species, with minimum inhibitory concentrations (MICs) typically in the range of 100-500 μg/mL. It also shows antifungal activity against Candida albicans. As an antioxidant, it effectively scavenges DPPH radicals and reduces lipid peroxidation. In cell culture, p-anisic acid inhibits LPS-induced NO production in macrophages, indicating anti-inflammatory potential.
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| ln Vivo |
In vivo, p-anisic acid has been evaluated for its anti-inflammatory effects in animal models. In carrageenan-induced paw edema in rats, p-anisic acid significantly reduced paw swelling at doses of 50-200 mg/kg orally. It also demonstrated hepatoprotective activity against CCl4-induced liver injury in mice, lowering serum transaminase levels. Its antimicrobial efficacy has been tested in topical formulations for skin infections, showing reduction in bacterial load.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays are not typical for p-anisic acid because it acts as a general antimicrobial and antioxidant rather than a specific enzyme inhibitor. However, its antioxidant activity can be assessed using DPPH or ABTS radical scavenging assays, where the IC50 for radical scavenging is determined. Its antimicrobial activity is tested by broth dilution or disc diffusion methods to determine MICs. No specific receptor binding assays are performed.
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| Cell Assay |
In vitro cellular assays for p-anisic acid are performed using macrophage cell lines (e.g., RAW 264.7) to evaluate anti-inflammatory activity. Cells are treated with p-anisic acid and stimulated with LPS, and NO production is measured by Griess assay. Cytokine levels (TNF-α, IL-6) are measured by ELISA. Cell viability is assessed by MTT. For antioxidant studies, cells are exposed to oxidative stress (e.g., H2O2), and cell survival and ROS levels are measured using fluorescent probes.
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| Animal Protocol |
In vivo animal experiments for p-anisic acid are conducted in rodent models. For anti-inflammatory testing, rats are given p-anisic acid orally, and paw edema is induced by carrageenan. Edema volume is measured plethysmographically. For hepatoprotection, mice are pretreated with p-anisic acid before CCl4 injection, and serum ALT/AST and liver histology are examined. In topical antimicrobial studies, skin infections are induced in mice, and the compound is applied; bacterial counts are determined.
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| ADME/Pharmacokinetics |
p-Anisic acid has a molecular weight of 152.15 g/mol and a molecular formula of C8H8O3. It is a white crystalline solid, soluble in ethanol, methanol, and acetone, but sparingly soluble in water. The compound has a melting point of 184-186°C. It is stable under normal conditions. Pharmacokinetic data in humans are limited; in rats, it is absorbed after oral administration, metabolized by conjugation, and excreted in urine. Its oral bioavailability is moderate.
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| Toxicity/Toxicokinetics |
p-Anisic acid is generally regarded as safe (GRAS) for use as a food additive and in cosmetics. It is non-toxic at typical usage levels. Acute oral LD50 in rats is >5000 mg/kg, indicating low toxicity. Skin irritation is minimal. However, high doses may cause gastrointestinal upset. There is no evidence of carcinogenicity or mutagenicity. It is considered safe for topical application in cosmetic products up to certain concentrations.
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| References | |
| Additional Infomation |
4-Methoxybenzoic acid is a methoxybenzoic acid compound with a methoxy group substituted at the C-4 position. It is a plant metabolite functionally related to benzoic acid and is the conjugate acid of 4-methoxybenzoic acid esters. It has been reported in rhododendron dauricum, aconite (Aconitum forrestii), and other organisms with relevant data. Anisic acid is a metabolite found or produced in Saccharomyces cerevisiae. See also: Stevia rebaudiuna leaves (partial).
p-Anisic acid is a naturally occurring phenolic acid used as a preservative and flavoring agent in foods, cosmetics, and pharmaceuticals. Its antimicrobial and antioxidant properties make it useful in preserving personal care products. It is also used as an intermediate in the synthesis of other compounds, including pharmaceuticals and agrochemicals. p-Anisic acid is not a drug but serves as a safe ingredient in many consumer products. Its safety and efficacy are well established. |
| Molecular Formula |
C8H8O
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|---|---|
| Molecular Weight |
152.15
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| Exact Mass |
152.047
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| CAS # |
100-09-4
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| Related CAS # |
p-Anisic acid-13C6;1173022-97-3;p-Anisic acid-d4;152404-46-1
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| PubChem CID |
7478
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| Appearance |
White to off-white solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
278.3±13.0 °C at 760 mmHg
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| Melting Point |
182-185 °C(lit.)
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| Flash Point |
115.5±13.3 °C
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| Vapour Pressure |
0.0±0.6 mmHg at 25°C
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| Index of Refraction |
1.546
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| LogP |
1.96
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
11
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| Complexity |
136
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| Defined Atom Stereocenter Count |
0
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| SMILES |
COC1=CC=C(C=C1)C(=O)O
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| InChi Key |
ZEYHEAKUIGZSGI-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C8H8O3/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5H,1H3,(H,9,10)
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| Chemical Name |
4-methoxybenzoic acid
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| Synonyms |
NSC-32742; NSC 32742; p-Anisic 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 (~657.25 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (16.43 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 (16.43 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 (16.43 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 | 6.5725 mL | 32.8623 mL | 65.7246 mL | |
| 5 mM | 1.3145 mL | 6.5725 mL | 13.1449 mL | |
| 10 mM | 0.6572 mL | 3.2862 mL | 6.5725 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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