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Lactaldehyde

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Lactaldehyde
Skeletal formula
Skeletal formula
Ball-and-stick model of L-lactaldehyde
Ball-and-stick model of L-lactaldehyde
Names
IUPAC name 2-Hydroxypropanal
Other names Hydroxypropionaldehyde
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.237.284 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H6O2/c1-3(5)2-4/h2-3,5H,1H3Key: BSABBBMNWQWLLU-UHFFFAOYSA-N
  • InChI=1/C3H6O2/c1-3(5)2-4/h2-3,5H,1H3Key: BSABBBMNWQWLLU-UHFFFAOYAY
SMILES
  • O=CC(O)C
Properties
Chemical formula C3H6O2
Molar mass 74.079 g·mol
Related compounds
Related aldehydes Glycolaldehyde

3-Hydroxybutanal

Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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:

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.

References

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