: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

3-Hydroxybutanal

}}

}}

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}}

References