23Dihydroxypropanal

2,3-Dihydroxypropanal, commonly known as glyceraldehyde, is the simplest aldose sugar. Its molecular formula is C3H6O3, with a molar mass of about 90.08 g/mol. As a triose, it contains an aldehyde group at the first carbon and hydroxyl groups on the second and third carbons.

There are two enantiomeric forms: D-glyceraldehyde and L-glyceraldehyde. D-glyceraldehyde is dextrorotatory and is used as a reference for the stereochemistry of biologically important monosaccharides. In biochemistry, glyceraldehyde is frequently discussed in relation to glyceraldehyde-3-phosphate, an essential intermediate in glycolysis and in the Calvin cycle.

In solution, glyceraldehyde can undergo interconversion with dihydroxyacetone through enediolization, a reaction relevant to carbohydrate metabolism and the spectroscopy of sugars. This is part of the constitutional isomerism observed among triose sugars.

Chemical reactions of glyceraldehyde include oxidation of the aldehyde to glyceric acid and reduction to glycerol. It can be produced synthetically by oxidation of glycerol or by selective transformations of sugars, and it also occurs transiently in biological systems as a metabolic intermediate, especially in pathways involving triose phosphate equilibria.

Glyceraldehyde is a small, highly soluble carbohydrate and serves as a fundamental reference compound in carbohydrate chemistry and stereochemistry. Its simple structure makes it a classic example in studies of sugar reactivity, enzymology, and the behavior of aldose sugars.