Chemistry:Lactaldehyde

Lactaldehyde

Names
IUPAC name 2-Hydroxypropanal
Other names Hydroxypropionaldehyde
Identifiers
CAS Number	598-35-6 Y 3946-09-6 (R) Y 3913-64-2 (S) Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:18419 Y
ChemSpider	832 Y
KEGG	C05999 Y
PubChem CID	855
UNII	S468FB0QE4 Y
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
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

Tracking categories (test):

• PairSizeSet

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.