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general/hydroxy-aldehydes

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Lactaldehyde

3-Hydroxybutanal

Lactaldehyde is an intermediate in the methylglyoxal metabolic pathway. Methylglyoxal is converted to D-lactaldehyde by glycerol dehydrogenase (gldA). Lactaldehyde is then oxidized to lactic acid by aldehyde dehydrogenase.

Structure

Lactaldehyde is a three-carbon atom species with a carbonyl group on the first carbon atom (making it an aldehyde), and a hydroxy group on the second carbon atom, making it a secondary alcohol. The molecule is chiral, its stereocenter being located on the second carbon atom.

Lactaldehyde exists in several forms: in open-chain form and as cyclic hemiacetal; in solution and in crystal forms; as monomer and as dimer. In crystal form, three conformers occur as hemiacetal dimers with a 1,4-dioxane ring skeleton:

In equilibrium solution, negligibly small amounts of the monomer and at least one five-membered ring dimer exist.

References

References

  1. (1958). "The metabolism of lactaldehyde, page 205". J. Biol. Chem..
  2. (1983). "Conformational studies of DL-lactaldehyde by 1H-NMR, Raman and i.r. spectroscopy". Spectrochimica Acta Part A: Molecular Spectroscopy.
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hydroxy-aldehydes secondary-alcohols
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