Alpha hydroxycarboxylic acid
any carboxylic acid having hydroxyl group attached to α position in relation to carboxyl group
Alpha hydroxy carboxylic acids, or α-hydroxy carboxylic acids (AHAs), are a group of carboxylic acids featuring a hydroxy group located one carbon atom away from the acid group. This structural aspect distinguishes them from beta hydroxy acids, where the functional groups are separated by two carbon atoms. Notable AHAs include glycolic acid, lactic acid, mandelic acid, and citric acid.
α-Hydroxy acids are stronger acids compared to their non-alpha hydroxy counterparts, a property enhanced by internal hydrogen bonding. AHAs serve a dual purpose: industrially, they are utilized as additives in animal feed and as precursors for polymer synthesis. In cosmetics, they are commonly used for their ability to chemically exfoliate the skin.
Occurrence
Aldonic acids, a type of sugar acid, are a class of naturally occurring hydroxycarboxylic acids. They have the general chemical formula, HO2C(CHOH)nCH2OH. Gluconic acid, a particularly common aldonic acid, the oxidized derivative of glucose.
2-Hydroxy-4-(methylthio)butyric acid is an intermediate in the biosynthesis of 3-dimethylsulfoniopropionate, precursor to natural dimethyl sulfide.
Synthesis
One common synthesis hydrolyzes the relatively common α-halocarboxylic acids to produce 2-hydroxycarboxylic acids.
The public source identifies “Alpha hydroxycarboxylic acid” as any carboxylic acid having hydroxyl group attached to α position in relation to carboxyl group. This brief keeps that definition visible, then builds a research path around Alpha, hydroxycarboxylic and acid.
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