Lactaldehyde

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Lactaldehyde
Skeletal formula
Ball-and-stick model of L-lactaldehyde
Names
IUPAC name
2-Hydroxypropanal
Other names
Hydroxypropionaldehyde
Identifiers
3D model (Jmol)
ChEBI
ChemSpider
ECHA InfoCard 100.237.284
KEGG
Properties
C3H6O2
Molar mass 74.08 g·mol−1
Related compounds
Related aldehydes
Glycolaldehyde

3-Hydroxybutanal

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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]

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:

Dimerization of lactaldehyde leads to a mixture of stereoisomeric 1,4-dioxanes.

In equilibrium solution, negligibly small amounts of the monomer and at least one five-membered ring dimer exist.[2]

References[edit]

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