Lactaldehyde Explained

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.[1]

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.[2]

Notes and References

  1. Pien Chien Huang . Huang PC. Miller ON . The metabolism of lactaldehyde, page 205. J. Biol. Chem. . 231 . 1 . 201–5 . 1958 . 10.1016/S0021-9258(19)77298-6 . 13538961 . free .
  2. 10.1016/0584-8539(83)80108-1 . Conformational studies of DL-lactaldehyde by 1H-NMR, Raman and i.r. spectroscopy . 1983 . Takahashi . H . Spectrochimica Acta Part A: Molecular Spectroscopy . 39 . 6 . 569–572.