Lactaldehyde
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| Names | |||
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| IUPAC name
2-Hydroxypropanal
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| Other names
Hydroxypropionaldehyde
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3D model (JSmol)
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PubChem CID
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| Properties | |||
| C3H6O2 | |||
| Molar mass | 74.079 g·mol−1 | ||
| Related compounds | |||
Related aldehydes
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Glycolaldehyde | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Template:Chembox Footer/trackingTemplate:Short description
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:
In equilibrium solution, negligibly small amounts of the monomer and at least one five-membered ring dimer exist.[2]
References
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- ^ Page Module:Citation/CS1/styles.css has no content.Huang PC; Miller ON (1958). "The metabolism of lactaldehyde, page 205" (PDF). J. Biol. Chem. 231 (1): 201–5. doi:10.1016/S0021-9258(19)77298-6. PMID 13538961.
- ^ Page Module:Citation/CS1/styles.css has no content.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.
