Lactaldehyde

Lactaldehyde
Skeletal formula	Ball-and-stick model of L-lactaldehyde
Names
	IUPAC name 2-Hydroxypropanal
	Other names Hydroxypropionaldehyde
Identifiers
CAS Number	598-35-6 ; 3946-09-6 (R) ; 3913-64-2 (S) ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:18419 ;
ChemSpider	832 ;
ECHA InfoCard	100.237.284
KEGG	C05999 ;
PubChem CID	855;
	InChI InChI=1S/C3H6O2/c1-3(5)2-4/h2-3,5H,1H3 Key: BSABBBMNWQWLLU-UHFFFAOYSA-N ; InChI=1/C3H6O2/c1-3(5)2-4/h2-3,5H,1H3 Key: BSABBBMNWQWLLU-UHFFFAOYAY;
	SMILES O=CC(O)C;
Properties
Chemical formula	C3H6O2
Molar mass	74.079 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]

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.^[2]

References

↑ Huang PC; Miller ON (1958). "The metabolism of lactaldehyde, page 205" (PDF). J. Biol. Chem. 231 (1): 201–5. PMID 13538961.
↑ 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.

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[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.

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