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Salicylic acid (Molecule of the Month for January 2008)

BHA, Chemical Peel



Salicylic acid (from the Latin word for the willow tree, Salix, from whose bark it can be obtained) is a beta hydroxy acid (BHA) where the OH group is adjacent to the carboxyl group. This colorless crystalline organic acid is widely used in organic synthesis and functions as a plant hormone generating a significant impact on plant growth and development, photosynthesis, transpiration, ion uptake and transport and also induces specific changes in leaf anatomy and chloroplast structure. It is derived from the metabolism of salicin. It is probably best known as a compound that is chemically similar but not identical to the active component of aspirin.

The Greek physician Hippocrates wrote in the 5th century BC about a bitter powder extracted from willow bark that could ease aches and pains and reduce fevers. This remedy was also mentioned in texts from ancient Sumer, Lebanon, and Assyria. The Cherokee and other Native Americans used an infusion of the bark for fever and other medicinal purposes for centuries. The medicinal part of the plant is the inner bark and was used as a pain reliever for a variety of ailments. The Reverend Edward (Edmund) Stone, a vicar from Chipping Norton, Oxfordshire, England, noted in 1763 that the bark of the willow was effective in reducing a fever. The active extract of the bark, called salicin, after the Latin name for the white willow (Salix alba), was isolated in crystalline form in 1828 by Henri Leroux, a French pharmacist, and Raffaele Piria, an Italian chemist. Piria was able to convert the substance into a sugar and a second component, which on oxidation becomes salicylic acid.

salicylic acid is a key ingredient in many skin-care products for the treatment of acne, psoriasis, calluses, corns, keratosis pilaris, and warts. It works by causing the cells of the epidermis to slough off more readily, preventing pores from clogging up, and allowing room for new cell growth. Because of its effect on skin cells, salicylic acid is used in several shampoos used to treat dandruff. Salicylic acid is also used as an active ingredient in gels which remove warts. Use of concentrated solutions of salicylic acid may cause hyperpigmentation on unpretreated skin for those with darker skin types (Fitzpatrick phototypes IV, V, VI), as well as with the lack of use of a broad spectrum sunblock.

Formal Chemical Name (IUPAC)
2-hydroxybenzoic acid

References

http://en.wikipedia.org/wiki/Salicylic_acid

Picture of Salicylic acid

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Picture of Salicylic acid

C7 H6 O3



Update by Karl Harrison
(Molecule of the Month for January 2008 )