4-Methoxybenzoic acid – a phenolic acid with low toxicity

4-Methoxybenzoic acid, also known as p-anisic acid, 4-anisate or draconic acid, belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position C-4 of the benzene ring is replaced by a methoxy group. It has a role as a plant metabolite. It derives from a benzoic acid. It is a conjugate acid of a 4-methoxybenzoate.

4-Methoxybenzoic acid is a phenolic acid, an organic molecule commonly found in anis-seed, a common food spice. 4-Methoxybenzoic acid is occasionally found in human biofluids. 4-Methoxybenzoic acid has been characterized as a classical non-competitive inhibitor of the oxidation of L-3, 4-dihydroxyphenylalanine (L-DOPA), and the hydroxylation of L-tyrosine catalyzed by tyrosinase. Additionally, anisic acid is a metabolite of aniracetam, a cognition enhancer [1].

4-Methoxybenzoic acid is found naturally in anise. It is a white crystalline solid which is insoluble in water, highly soluble in alcohols and soluble in ether, and ethyl acetate. 4-Methoxybenzoic acid has antiseptic properties. It is also used as an intermediate in the preparation of more complex organic compounds. It is generally obtained by the oxidation of anethole or p-methoxyacetophenone [2].

 
4-Methoxybenzoic acid is a drug. 4-Methoxybenzoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Methoxybenzoic acid exists in all eukaryotes, ranging from yeast to humans. 4-Methoxybenzoic acid is a faint, sweet, and cadaverous tasting compound. Outside of the human body, 4-Methoxybenzoic acid has been detected, but not quantified in, several different foods, such as anises, cocoa beans, fennels, and German camomiles. This could make 4-Methoxybenzoic acid a potential biomarker for the consumption of these foods. It is a white crystalline solid which is insoluble in water, highly soluble in alcohols and soluble in ether, and ethyl acetate. 4-Methoxybenzoic acid has antiseptic properties. It is also used as an intermediate in the preparation of more complex organic compounds. It is generally obtained by the oxidation of anethole or p-methoxyacetophenone. 4-Methoxybenzoic acid is generally classified as having a low toxicity rating.

References

[1] https://pubchem.ncbi.nlm.nih.gov/compound/4-Methoxybenzoic-acid

[2] https://en.wikipedia.org/wiki/P-Anisic_aci