Lactaldehyde

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.

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

ECHA InfoCard

100.237.284

KEGG

C05999^Y

PubChem CID

855

UNII

S468FB0QE4^Y

CompTox Dashboard (EPA)

DTXSID60862267

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

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:

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