Salicylic acid is a compound with a phenolic ring and a carboxylic acid group. It has a molecular formula of C7H6O3 and a molecular weight o...
Salicylic acid is a compound with a phenolic ring and a carboxylic acid group. It has a molecular formula of C7H6O3 and a molecular weight of 138.12 g/mol. It is a widely used compound in medicine, especially in the treatment of acne and psoriasis, and is also used as a food preservative and as a precursor for the production of other chemicals.
The structure-activity relationship (SAR) of salicylic acid can be explored by examining the effects of modifications to its structure on its biological activity.
Phenolic ring:
The presence of the phenolic ring in salicylic acid is important for its activity. Modification of the ring, such as substitution of the hydroxyl group with a methyl or ethyl group, results in a decrease in activity.
Carboxylic acid group:
The carboxylic acid group in salicylic acid is also important for its activity. Removal or modification of this group results in a decrease in activity.
Position of the hydroxyl group:
The hydroxyl group in salicylic acid is located at the ortho position relative to the carboxylic acid group. Substitution of the hydroxyl group with a methyl group at this position results in a decrease in activity.
Stereochemistry:
The stereochemistry of salicylic acid is important for its activity. The (S)-enantiomer is more active than the (R)-enantiomer.
Lipophilicity:
The lipophilicity of salicylic acid is important for its activity. Increasing the lipophilicity of the molecule through the addition of alkyl groups or the introduction of a bulky substituent at the ortho position results in an increase in activity.
Overall, the SAR of salicylic acid suggests that the phenolic ring and carboxylic acid group are essential for its activity, while modifications to the hydroxyl group, stereochemistry, and lipophilicity can affect its potency.
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