Lactaldehyde

Lactaldehyde

IUPAC name 2-Hydroxypropanal
Other names Hydroxypropionaldehyde
Identifiers
CAS number	598-35-6^Y, 3946-09-6 (R)^Y, 3913-64-2 (S)^Y
PubChem	855
ChemSpider	832^Y
KEGG	C05999^Y
ChEBI	CHEBI:18419^Y
Jmol-3D images	Image 1
SMILES O=CC(O)C
InChI InChI=1S/C3H6O2/c1-3(5)2-4/h2-3,5H,1H3^Y Key: BSABBBMNWQWLLU-UHFFFAOYSA-N^Y InChI=1/C3H6O2/c1-3(5)2-4/h2-3,5H,1H3 Key: BSABBBMNWQWLLU-UHFFFAOYAY
Properties
Molecular formula	C₃H₆O₂
Molar mass	74.08 g mol⁻¹
Related compounds
Related aldehydes	Glycolaldehyde 3-Hydroxybutanal
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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. In equilibrium solution, negligibly small amounts of the monomer and at least one five-membered ring dimer exist.^[2]

References

^ Huang PC, Miller ON (1958). "The metabolism of lactaldehyde, page 205". J. Biol. Chem. 231 (1): 201–5. PMID 13538961. http://www.jbc.org/content/231/1/201.full.pdf.
^ 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.