:Lactaldehyde
{{chembox
| Watchedfields = changed
| verifiedrevid = 444424686
| ImageFileL1 = lactaldehyde.svg
| ImageSizeL1 = 110
| ImageNameL1 = Skeletal formula
| ImageFileR1 = L-Lactaldehyde molecule ball.png
| ImageSizeR1 = 130
| ImageNameR1 = Ball-and-stick model of L-lactaldehyde
| IUPACName = 2-Hydroxypropanal
| OtherNames = Hydroxypropionaldehyde
|Section1={{Chembox Identifiers
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C05999
| InChI = 1/C3H6O2/c1-3(5)2-4/h2-3,5H,1H3
| InChIKey = BSABBBMNWQWLLU-UHFFFAOYAY
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C3H6O2/c1-3(5)2-4/h2-3,5H,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BSABBBMNWQWLLU-UHFFFAOYSA-N
| CASNo=598-35-6
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = S468FB0QE4
| CASNo1=3946-09-6
| CASNo1_Ref = {{cascite|correct|CAS}}
| CASNo1_Comment = (R)
| CASNo2=3913-64-2
| CASNo2_Ref = {{cascite|correct|CAS}}
| CASNo2_Comment = (S)
| PubChem=855
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 832
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 18419
| SMILES = O=CC(O)C
}}
|Section2={{Chembox Properties
| C=3 | H=6 | O=2
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
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|Section3={{Chembox Related
| OtherFunction_label = aldehydes
| OtherFunction = Glycolaldehyde
}}
}}
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.{{cite journal|author-link1=Pien Chien Huang |author1=Huang PC|author2=Miller ON |title=The metabolism of lactaldehyde, page 205|journal=J. Biol. Chem. |volume=231 |issue=1 |pages=201–5 |year=1958 |doi=10.1016/S0021-9258(19)77298-6 |pmid=13538961 | url = http://www.jbc.org/content/231/1/201.full.pdf|doi-access=free }}
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:
File:Lactaldehyde dimerization V1.svg{{clear-left}}
In equilibrium solution, negligibly small amounts of the monomer and at least one five-membered ring dimer exist.{{cite journal | doi = 10.1016/0584-8539(83)80108-1 | title = Conformational studies of DL-lactaldehyde by 1H-NMR, Raman and i.r. spectroscopy | year = 1983 | last1 = Takahashi | first1 = H | journal = Spectrochimica Acta Part A: Molecular Spectroscopy | volume = 39 | issue = 6 | pages = 569–572}}