Hydroxycarboxylic acids

Hydroxycarboxylic acids

Stability (from top to bottom) of the hydroxy group in relation to the carboxy group : α-hydroxycarboxylic acids, β-hydroxycarboxylic acids and γ-hydroxycarboxylic acids.

Hydroxycarboxylic acids (also hydroxy acids , obsolete oxy acids ) are carboxylic acids that have at least one carboxy group as well as one or more hydroxyl group (s).

α-hydroxycarboxylic acids

α- Hydroxycarboxylic acids ( synonym : alpha-hydroxy acids ; English : Alpha hydroxy acids , AHA ) are hydroxycarboxylic acids in which the hydroxyl group is located on the carbon atom adjacent to the carboxy group. Many representatives occurnaturallyas so-called fruit acids .

Important α-hydroxycarboxylic acids:

Malic acid , the hydroxy analog of aspartic acid
Citric acid
2-Hydroxy-4-methylmercaptobutyric acid, the hydroxy analog of the amino acid methionine
Glycolic acid , the hydroxy analog of the amino acid glycine
Isocitric acid
Mandelic acid
Lactic acid , the hydroxy analog of the amino acid alanine
Tartronic acid
Tartaric acid

β-hydroxycarboxylic acids

β- Hydroxycarboxylic acids ( synonym : beta-hydroxy acids ; English : Beta hydroxy acids , BHA ) are hydroxycarboxylic acids in which there is another carbon atom between the carboxy group and the carbon atom that carries the hydroxyl group.

Important β-hydroxycarboxylic acids:

Other hydroxycarboxylic acids

Gallic acid
4-hydroxybutanoic acid (4-hydroxybutyric acid, liquid ecstasy)
Polyhydroxybutyric acid
Salicylic acid (2-hydroxybenzoic acid)
4-hydroxybenzoic acid (PHB)

Hydroxycarboxylic acids in nature (selection in pictures)

pineapple
Apples
Apricots
Bananas
Pears
blackberry
Strawberries
Grapefruit
Raspberries
Cherries
kiwi
Oranges
peach
plum
Black currants
Lemons

Individual evidence

↑ Axel Kleemann , Bernd Lehmann, Jürgen Martens: Enantioselective synthesis of the hydroxy analogs of D - and L -methionine . In: Angewandte Chemie . tape 91 , no. 10 , October 1979, p. 858-859 , doi : 10.1002 / anie.19790911028 . (or Enantioselective Synthesis of the Hydroxy-Analogues of D-and L-Methionine In: Angewandte Chemie International Edition in English. Volume 18, No. 10, October 1979, p. 797, doi: 10.1002 / anie.197907971 ).

[Kleemann-1] Axel Kleemann , Bernd Lehmann, Jürgen Martens: Enantioselective synthesis of the hydroxy analogs of D - and L -methionine . In: Angewandte Chemie . tape 91 , no. 10 , October 1979, p. 858-859 , doi : 10.1002 / anie.19790911028 . (or Enantioselective Synthesis of the Hydroxy-Analogues of D-and L-Methionine In: Angewandte Chemie International Edition in English. Volume 18, No. 10, October 1979, p. 797, doi: 10.1002 / anie.197907971 ).