O-Anisic acid, also known as 2-methoxybenzoic acid or 2-methoxybenzoic acid, is a crystalline solid. It is an organic compound with the molecular formula CH3OC6H4CO2H. It is a colorless solid and is one of the isomers of anisic acid. The compound has been extensively studied for its intramolecular hydrogen bonding and as a substrate in various catalytic reactions. The uses of O anisic acid have been reported in Chinese cuisine, cowpea, and other biological systems.

O anisic acid uses

Flavoring Agent

O-Anisic acid is used as a food additive to enhance the flavor or aroma of food.

Non-Steroidal Anti-Inflammatory Drug (NSAID)

It has NSAID properties, functioning as an anti-inflammatory agent without the use of steroids. Besides anti-inflammatory effects, NSAIDs also have analgesic, antipyretic, and platelet-inhibiting actions. They block the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid into cyclic endoperoxides, the precursors of prostaglandins.

Hydrogen Bond Research

Substituted benzoic acid compounds serve as good model molecules for studying hydrogen bonding. Studies by Margaret et al. have detailed the hydrogen bond arrangements of o-methoxybenzoic acid in solution and crystal forms, while Kharitonov and others have elucidated its intermolecular and intramolecular interactions in the gas phase. Parvez performed X-ray diffraction analysis on single crystals obtained from toluene and carbon tetrachloride (1:1), confirming that intermolecular hydrogen bonds form carboxyl dimers in the solid state. Wang Yan et al. used temperature-dependent infrared spectroscopy to find that o-methoxybenzoic acid in the solid state forms dimers and also exhibits tautomeric forms.

Carbon Supplement

Researchers have explored the potential use of 2-methoxybenzoic acid as a carbon source in bacterial culture media. For example, studies on the bacterium Moraxella osloensis have shown that it can utilize 2-methoxybenzoic acid as a carbon source for growth. This finding is significant for understanding bacterial metabolic processes and optimizing the design of specific microbial culture media.

Khaled M. Khleifat and others investigated the substrate range of 2,4-dinitrotoluene (DNT) dioxygenase by measuring substrate-dependent O2 uptake and maximum growth on basal medium containing the substrate (measured as A600). Control strains were not supplemented with specific substrates. Aromatic compounds tested as potential substrates included o-phenylenediamine, α-naphthylacetic acid, β-dimethylaminobenzaldehyde, 3,4-dinitrosalicylic acid, p-nitrophenol, naphthol, o-anisic acid, salicylic acid, toluene, and benzoic acid. Among all substrates used, only p-nitrophenol showed zero oxygen uptake and zero growth, indicating it is unlikely to be a substrate analog for 2,4-DNT. Wild-type Escherichia coli (JM103) and dnt-transformant (JS39) both used o-phenylenediamine as the sole carbon source. Using α-naphthylacetic acid and β-dimethylaminobenzaldehyde as substrates, DNT dioxygenase exhibited oxygen uptake rates of 11.8 and 14 μM/hr/mg protein, respectively. For six tested substrates (3,4-dinitrosalicylic acid, p-nitrophenol, o-anisic acid, salicylic acid, toluene, and benzoic acid), JS39 appeared to have a growth advantage, even though growth rates were lower than controls, similar to the results with α-naphthylacetic acid and β-dimethylaminobenzaldehyde.

Chemistry

O-Anisic acid is used as a precursor for synthesizing various organic compounds and as a reagent in analytical chemistry.

O anisic acid toxicity

According to the 2012 OSHA Hazard Communication Standard (29 CFR 1910.1200), O-anisic acid is classified as a hazardous chemical. It may cause irritation to the skin and eyes and can be an irritant to the respiratory tract. To ensure safety, it is recommended to avoid generating dust, inhaling mist, gases, or vapors, and direct contact with skin and eyes. Using personal protective equipment, such as chemical-resistant gloves, and ensuring good ventilation in the work environment are effective measures to prevent potential hazards.

O anisic acid msds

Hazards

• Eyes: Causes eye irritation.
• Skin: Causes skin irritation. Harmful if absorbed through the skin.
• Ingestion: May cause gastrointestinal irritation. Swallowing may be harmful.
• Inhalation: Causes respiratory irritation. Inhalation may be harmful.
• Chronic: Prolonged exposure to high concentrations may lead to central nervous system depression.

First Aid Measures

• Inhalation: Move the patient to fresh air.
• Skin Contact: Remove contaminated clothing and wash skin thoroughly with soap and water. Seek medical attention if discomfort persists.
• Eye Contact: Separate the eyelids and flush with flowing water or saline. Seek medical attention immediately.
• Ingestion: Rinse mouth; do not induce vomiting. Seek medical attention immediately.

Handling and Storage

• Safe Handling Precautions: Avoid contact with skin and eyes. Prevent dust and aerosol formation. Obtain special instructions before use. Provide appropriate exhaust ventilation in areas where dust is formed.
• Safe Storage Conditions: Store in a cool place. Keep container tightly closed and store in a dry, well-ventilated area.

Operational Precautions

• Personnel should be trained and strictly adhere to operating procedures.
• Handling should be done in facilities with local or general ventilation systems.
• Avoid contact with eyes and skin; avoid inhaling vapors.
• Keep away from sources of ignition and heat; no smoking in the workplace.
• Use explosion-proof ventilation systems and equipment.
• When transferring, control the flow rate and ensure grounding to prevent static buildup.
• Avoid contact with oxidizers and other incompatible substances.
• Handle with care to avoid damage to packaging and containers.
• Empty containers may retain hazardous residues.
• Wash hands after use; do not eat or drink in the workplace.
• Equip the workplace with appropriate fire-fighting equipment and emergency spill response equipment.

References:

[1]https://baike.baidu.com/item/%E9%82%BB%E7%94%B2%E6%B0%A7%E5%9F%BA%E8%8B%AF%E7%94%B2%E9%85%B8

[2]https://en.wikipedia.org/wiki/O-Anisic_acid

[3]https://fscimage.fishersci.com/msds/27128.htm

[4]https://www.ebi.ac.uk/chebi/chebiOntology.do?chebiId=CHEBI:421840

[5]Khleifat K M, Al-limoun M O, Alsharafa K Y, et al. Tendency of using different aromatic compounds as substrates by 2, 4-DNT dioxygenase expressed by pJS39 carrying the gene dntA from Burkholderia sp. strain DNT[J]. Bioremediation journal, 2019, 23(1): 22-31.

[6]Wang Yan, Sun Ziming, Dai Xiaochang, et al. Study on the temperature-dependent infrared spectrum of o-methoxybenzoic acid[J]. Yunnan Chemical Industry, 1992, (03): 5-6+12.

[7]https://pubchem.ncbi.nlm.nih.gov/compound/11370