Record Information
Version2.0
Creation Date2012-05-31 13:57:41 -0600
Update Date2015-09-17 15:41:16 -0600
Secondary Accession Numbers
  • ECMDB03052
Identification
Name:Lactaldehyde
DescriptionL-lactaldehyde is an intermediate metabolite in the pyruvate metabolism pathway. L-lactaldehyde is irreversibly produced from pyruvaldehyde via the enzyme aldehyde reductase (EC:1.1.1.21) which is then irreversibly converted to propylene glycol via aldehyde reductase (EC:1.1.1.21).
Structure
Thumb
Synonyms:
  • (+-)-2-Hydroxypropanal
  • (2S)-2-hydroxypropanal
  • (S)-lactaldehyde
  • 2-Hydroxypropanal
  • 2-Hydroxypropionaldehyde
  • a-Hydroxypropionaldehyde
  • Alpha-Hydroxypropionaldehyde
  • Hydroxypropionaldehyde
  • L-2-Hydroxypropionaldehyde
  • L-Lactaldehyde
  • Lactald
  • Lactaldehyde
  • α-Hydroxypropionaldehyde
Chemical Formula:C3H6O2
Weight:Average: 74.079
Monoisotopic: 74.036779433
InChI Key:BSABBBMNWQWLLU-UHFFFAOYSA-N
InChI:InChI=1S/C3H6O2/c1-3(5)2-4/h2-3,5H,1H3
CAS number:598-35-6
IUPAC Name:(2S)-2-hydroxypropanal
Traditional IUPAC Name:L-lactaldehyde
SMILES:[H]C(=O)C(C)O
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha-hydroxyaldehydes. These are organic compounds containing an aldehyde substituted with a hydroxyl group on the adjacent carbon.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-hydroxyaldehydes
Alternative Parents
Substituents
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility658 g/LALOGPS
logP-1ALOGPS
logP-0.63ChemAxon
logS0.95ALOGPS
pKa (Strongest Acidic)14.01ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity17.91 m³·mol⁻¹ChemAxon
Polarizability7.16 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
L-Fuculose 1-phosphate <> Dihydroxyacetone phosphate + Lactaldehyde + (S)-Lactaldehyde
Water + Lactaldehyde + NAD + (S)-Lactaldehyde <>2 Hydrogen ion + L-Lactic acid + NADH
Hydrogen ion + Lactaldehyde + NADH <> (S)-Propane-1,2-diol + NAD
L-Rhamnulose 1-phosphate <> Dihydroxyacetone phosphate + Lactaldehyde + (S)-Lactaldehyde
Lactaldehyde + NAD + Water <> L-Lactic acid + NADH + Hydrogen ion
Propylene glycol + NAD <> Lactaldehyde + NADH + Hydrogen ion
2-Dehydro-3-deoxy-L-rhamnonate <> Lactaldehyde + Pyruvic acid + (S)-Lactaldehyde
L-Fuculose 1-phosphate <> Dihydroxyacetone phosphate + Lactaldehyde
L-Rhamnulose 1-phosphate <> Dihydroxyacetone phosphate + Lactaldehyde
Water + NAD + Lactaldehyde > Hydrogen ion + NADH + L-Lactic acid
Hydrogen ion + NADH + Lactaldehyde <> NAD + Propylene glycol
Lactaldehyde + NADP < Pyruvaldehyde + NADPH + Hydrogen ion
2-keto-3-deoxy-L-rhamnonate Pyruvic acid + Lactaldehyde
Lactaldehyde + NAD + Water > L-Lactic acid + NADH
L-Fuculose 1-phosphate > Dihydroxyacetone phosphate + Lactaldehyde
(S)-Propane-1,2-diol + NAD > Lactaldehyde + NADH
L-Rhamnulose 1-phosphate > Dihydroxyacetone phosphate + Lactaldehyde
L-rhamnulose 1-phosphate + L-Rhamnulose 1-phosphate > Dihydroxyacetone phosphate + (S)-lactaldehyde + Lactaldehyde
L-fuculose 1-phosphate + L-Fuculose 1-phosphate > Dihydroxyacetone phosphate + (S)-lactaldehyde + Lactaldehyde
NAD + Water + (S)-lactaldehyde + Lactaldehyde > NADH +2 Hydrogen ion + L-Lactic acid + L-Lactic acid
(S)-lactaldehyde + NADH + Hydrogen ion + Lactaldehyde > NAD + Propylene glycol
Pyruvaldehyde + NADPH + Hydrogen ion > Lactaldehyde + NADP
2 2-Dehydro-3-deoxy-L-rhamnonate <> Lactaldehyde + Pyruvic acid + (S)-Lactaldehyde
SMPDB Pathways:
L-lactaldehyde degradation (aerobic)PW002073 ThumbThumb?image type=greyscaleThumb?image type=simple
fucose and rhamnose degradationPW000826 ThumbThumb?image type=greyscaleThumb?image type=simple
methylglyoxal degradation IVPW002078 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056v-9000000000-fe4416498788a968e467View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9300000000-12b08b93303d8cbf5c3aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-1aa2338222aff31e5e0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-9000000000-c450e557b2fe7c5dc5a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-dceca37df952939d1084View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-cd6930d73efb436bc0ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-97d1b594dd3b1d9b08b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-90fa8913085480b29a8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-9000000000-518c4b32efb3532122eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-9000000000-90bd5b8f63ecfac6a42aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-23a60e5f52ca732e0f56View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-feb30b99fe1a3132abb8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-9000000000-f5b28df550bdfcf22cc7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052s-9000000000-db6ce3d247485bf9581bView in MoNA
References
References:
  • Akhy MT, Brown CM, Old DC: L-Rhamnose utilisation in Salmonella typhimurium. J Appl Bacteriol. 1984 Apr;56(2):269-74. Pubmed: 6373710
  • Casazza JP, Felver ME, Veech RL: The metabolism of acetone in rat. J Biol Chem. 1984 Jan 10;259(1):231-6. Pubmed: 6706932
  • Chen YM, Chakrabarti T, Lin EC: Constitutive activation of L-fucose genes by an unlinked mutation in Escherichia coli. J Bacteriol. 1984 Aug;159(2):725-9. Pubmed: 6378890
  • Chen YM, Lin EC: Dual control of a common L-1,2-propanediol oxidoreductase by L-fucose and L-rhamnose in Escherichia coli. J Bacteriol. 1984 Mar;157(3):828-32. Pubmed: 6421801
  • Di Costanzo L, Gomez GA, Christianson DW: Crystal structure of lactaldehyde dehydrogenase from Escherichia coli and inferences regarding substrate and cofactor specificity. J Mol Biol. 2007 Feb 16;366(2):481-93. Epub 2006 Nov 10. Pubmed: 17173928
  • ENGLESBERG E: Physiological basis for rhamnose utilization by a mutant of Pasteurella pestis. I. Experiments with resting cells; the isolation of lactic aldehyde. J Bacteriol. 1957 Jul;74(1):8-11. Pubmed: 13462953
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Ros J, Aguilar J: Genetic and structural evidence for the presence of propanediol oxidoreductase isoenzymes in Escherichia coli. J Gen Microbiol. 1984 Mar;130(3):687-92. Pubmed: 6427403
  • SANDMAN RP, MILLER ON: Studies on the metabolism of lactaldehyde. I. Separation and determination of lactaldehyde and related 3-carbon compounds. J Biol Chem. 1958 Jan;230(1):353-9. Pubmed: 13502404
  • TING SM, MILLER ON, SELLINGER OZ: THE METABOLISM OF LACTALDEHYDE. VII. THE OXIDATION OF D-LACTALDEHYDE IN RAT LIVER. Biochim Biophys Acta. 1965 Mar 8;97:407-15. Pubmed: 14323585
  • TING SM, SELLINGER OZ, MILLER ON: THE METABOLISM OF LACTALDEHYDE. VI. THE REDUCTION OF D- AND L-LACTALDEHYDE IN RAT LIVER. Biochim Biophys Acta. 1964 Aug 26;89:217-25. Pubmed: 14203169
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Kranz, Cyrill. Synthesis of Lactic Aldehyde. Chemicke Listy pro Vedu a Prumysl (1912), 5 323-7.
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID18041
HMDB IDHMDB03052
Pubchem Compound ID439231
Kegg IDC05999
ChemSpider ID388368
WikipediaLactaldehyde
BioCyc IDLACTALD
EcoCyc IDLACTALD

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
(R)-propane-1,2-diol + NAD(+) = (R)- lactaldehyde + NADH
Gene Name:
fucO
Uniprot ID:
P0A9S1
Molecular weight:
40644
Reactions
(R)-propane-1,2-diol + NAD(+) = (R)-lactaldehyde + NADH.
(S)-propane-1,2-diol + NAD(+) = (S)-lactaldehyde + NADH.
General function:
Involved in metal ion binding
Specific function:
L-fuculose 1-phosphate = glycerone phosphate + (S)-lactaldehyde
Gene Name:
fucA
Uniprot ID:
P0AB87
Molecular weight:
23775
Reactions
L-fuculose 1-phosphate = glycerone phosphate + (S)-lactaldehyde.
General function:
Involved in oxidoreductase activity
Specific function:
Acts on lactaldehyde as well as other aldehydes
Gene Name:
aldA
Uniprot ID:
P25553
Molecular weight:
52272
Reactions
(S)-lactaldehyde + NAD(+) + H(2)O = (S)-lactate + NADH.
Glycolaldehyde + NAD(+) + H(2)O = glycolate + NADH.
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the reduction of 2,5-diketo-D-gluconic acid (25DKG) to 2-keto-L-gulonic acid (2KLG)
Gene Name:
dkgB
Uniprot ID:
P30863
Molecular weight:
29437
Reactions
2-dehydro-D-gluconate + NADP(+) = 2,5-didehydro-D-gluconate + NADPH.
General function:
Involved in metal ion binding
Specific function:
Catalyzes the reversible cleavage of L-rhamnulose-1- phosphate to dihydroxyacetone phosphate (DHAP) and L-lactaldehyde
Gene Name:
rhaD
Uniprot ID:
P32169
Molecular weight:
30145
Reactions
L-rhamnulose 1-phosphate = glycerone phosphate + (S)-lactaldehyde.
General function:
Involved in carbon-carbon lyase activity
Specific function:
Catalyzes the reversible retro-aldol cleavage of 2-keto- 3-deoxy-L-rhamnonate (KDR) to pyruvate and lactaldehyde. 2-keto-3- deoxy-L-mannonate, 2-keto-3-deoxy-L-lyxonate and 4-hydroxy-2- ketoheptane-1,7-dioate (HKHD) are also reasonably good substrates, although 2-keto-3-deoxy-L-rhamnonate is likely to be the physiological substrate
Gene Name:
rhmA
Uniprot ID:
P76469
Molecular weight:
28916
Reactions
2-dehydro-3-deoxy-L-rhamnonate = pyruvate + (R)-lactaldehyde.
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the reduction of 2,5-diketo-D-gluconic acid (25DKG) to 2-keto-L-gulonic acid (2KLG). It is also capable of stereoselective -keto ester reductions on ethyl acetoacetate and other 2-substituted derivatives
Gene Name:
dkgA
Uniprot ID:
Q46857
Molecular weight:
31109
Reactions
2-dehydro-D-gluconate + NADP(+) = 2,5-didehydro-D-gluconate + NADPH.
General function:
Involved in metal ion binding
Specific function:
Specific function unknown
Gene Name:
ygbL
Uniprot ID:
Q46890
Molecular weight:
23222