Salicylic acid

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159.0 °C, 432 K, 318 °F

211 °C (20 mmHg)

Salicylic acid (from Latin salix, willow tree, from the bark of which the substance is obtained) is a monohydroxybenzoic acid, a type of phenolic acid and a beta hydroxy acid. This colorless crystalline organic acid is widely used in organic synthesis and functions as a plant hormone. It is derived from the metabolism of salicin. In addition to being a compound that is chemically similar to but not identical to the active component of aspirin (acetylsalicylic acid), it is probably best known for its use in anti-acne treatments. The salts and esters of salicylic acid are known as salicylates.

Contents

Chemistry

Salicylic acid has the formula C6H4(OH)COOH, where the OH group is ortho to the carboxyl group. It is also known as 2-hydroxybenzenecarboxcylic acid. It is poorly soluble in water (0.2 g/100 ml H2O at 20 °C).[3] Aspirin (acetylsalicylic acid or ASA) can be prepared by the esterification of the phenolic hydroxyl group of salicylic acid with the acetate ion from acetic acid.

Plant hormone

Salicylic acid (SA) is a phenolic phytohormone and is found in plants with roles in plant growth and development, photosynthesis, transpiration, ion uptake and transport. SA also induces specific changes in leaf anatomy and chloroplast structure. SA is involved in endogenous signaling, mediating in plant defense against pathogens.[4] It plays a role in the resistance to pathogens by inducing the production of pathogenesis-related proteins.[5] It is involved in the systemic acquired resistance (SAR) in which a pathogenic attack on one part of the plant induces resistance in other parts. The signal can also move to nearby plants by salicyclic acid being converted to the volatile ester, methyl salicylate.[6]

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