Record Information
Version2.0
Creation Date2012-05-31 13:55:54 -0600
Update Date2015-09-13 12:56:12 -0600
Secondary Accession Numbers
  • ECMDB02165
Identification
Name:Glycolaldehyde
DescriptionGlycolaldehyde (HOCH2-CH=O, IUPAC name 2-hydroxyethanal) is a type of diose (2-carbon monosaccharide). Glycolaldehyde is readily converted to acetyl coenzyme A. It has an aldehyde and a hydroxyl group. However, it is not actually a sugar, because there is only one hydroxyl group. Glycolaldehyde is formed from many sources, including the amino acid glycine and from purone catabolism. It can form by action of ketolase on fructose 1,6-bisphosphate in an alternate glycolysis pathway. This compound is transferred by thiamin pyrophosphate during the pentose phosphate shunt.
Structure
Thumb
Synonyms:
  • 2-Hydroxyacetaldehyde
  • 2-Hydroxyethanal
  • 2-OH-acetaldehyde
  • 2-Oxoethanol
  • Diose
  • Glycoaldehyde
  • Glycolaldehyde
  • Glycolic aldehyde
  • Glycollaldehyde
  • Hydroxyacetaldehyde
  • Hydroxyethanal
  • Methylol formaldehyde
  • Methylolformaldehyde
  • Monomethylolformaldehyde
Chemical Formula:C2H4O2
Weight:Average: 60.052
Monoisotopic: 60.021129372
InChI Key:WGCNASOHLSPBMP-UHFFFAOYSA-N
InChI:InChI=1S/C2H4O2/c3-1-2-4/h1,4H,2H2
CAS number:141-46-8
IUPAC Name:2-hydroxyacetaldehyde
Traditional IUPAC Name:glycolaldehyde
SMILES:OCC=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as short-chain aldehydes. These are an aldehyde with a chain length containing between 2 and 5 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentShort-chain aldehydes
Alternative Parents
Substituents
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:97 °C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility725 g/LALOGPS
logP-0.99ALOGPS
logP-1.2ChemAxon
logS1.08ALOGPS
pKa (Strongest Acidic)14.27ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity13.42 m³·mol⁻¹ChemAxon
Polarizability5.32 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
D-arabinose degradation IPW002038 ThumbThumb?image type=greyscaleThumb?image type=simple
Ethylene Glycol DegradationPW002093 ThumbThumb?image type=greyscaleThumb?image type=simple
Folate biosynthesisPW000908 ThumbThumb?image type=greyscaleThumb?image type=simple
GTP degradationPW001888 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, Positivesplash10-03di-9000000000-c2f1922c3cfc298b56e6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0109-9200000000-6143e9afd72b9d7c5b6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-666acd064bdf4b7e4e17View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-f129f99fe312906de2f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-a4339f6764dcb3e35133View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-9aad7766f88c7ab6028bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9000000000-8dee0ff3027177f894d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-f167702c9efe9cfcd0a8View in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-86c6c734f49f41d961f7View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Choei H, Sasaki N, Takeuchi M, Yoshida T, Ukai W, Yamagishi S, Kikuchi S, Saito T: Glyceraldehyde-derived advanced glycation end products in Alzheimer's disease. Acta Neuropathol (Berl). 2004 Sep;108(3):189-93. Epub 2004 Jun 17. Pubmed: 15221334
  • 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
  • Takeuchi M, Yamagishi S: TAGE (toxic AGEs) hypothesis in various chronic diseases. Med Hypotheses. 2004;63(3):449-52. Pubmed: 15288366
  • 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
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Majerski, Piotr A.; Piskorz, Jan K.; Radlein, Desmond St. A. G. Production of glycolaldehyde by hydrous thermolysis of sugars. PCT Int. Appl. (2002), 41 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID17071
HMDB IDHMDB03344
Pubchem Compound ID756
Kegg IDC00266
ChemSpider ID736
WikipediaGlycolaldehyde
BioCyc IDGLYCOLALDEHYDE
EcoCyc IDGLYCOLALDEHYDE

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 dihydroneopterin aldolase activity
Specific function:
Catalyzes the conversion of 7,8-dihydroneopterin to 6- hydroxymethyl-7,8-dihydropterin. Can use L-threo-dihydroneopterin and D-erythro-dihydroneopterin as substrates for the formation of 6-hydroxymethyldihydropterin, but it can also catalyze the epimerization of carbon 2' of dihydroneopterin and dihydromonapterin at appreciable velocity
Gene Name:
folB
Uniprot ID:
P0AC16
Molecular weight:
13619
Reactions
2-amino-4-hydroxy-6-(D-erythro-1,2,3-trihydroxypropyl)-7,8-dihydropteridine = 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine + glycolaldehyde.
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 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 alkanesulfonate monooxygenase activity
Specific function:
Involved in desulfonation of aliphatic sulfonates. Catalyzes the conversion of pentanesulfonic acid to sulfite and pentaldehyde and is able to desulfonate a wide range of sulfonated substrates including C-2 to C-10 unsubstituted linear alkanesulfonates, substituted ethanesulfonic acids and sulfonated buffers
Gene Name:
ssuD
Uniprot ID:
P80645
Molecular weight:
41736
Reactions
An alkanesufonate (R-CH(2)-SO(3)H) + FMNH(2) + O(2) = an aldehyde (R-CHO) + FMN + sulfite + H(2)O.