Glycolaldehyde

Glycolaldehyde
IUPAC name

2-hydroxyacetaldehyde
Identifiers
CAS number 141-46-8 Y
PubChem 756
ChemSpider 736 Y
KEGG C00266 Y
ChEBI CHEBI:17071 Y
Jmol-3D images Image 1
Properties
Molecular formula C2H4O2
Molar mass 60.052 g/mol
Related compounds
Related aldehydes 3-Hydroxybutanal

Lactaldehyde
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Glycolaldehyde (HOCH2-CH=O) is the smallest possible molecule that contains both an aldehyde group and a hydroxyl group. It is the only possible diose, a 2-carbon monosaccharide, although a diose is not strictly a saccharide. It is the simplest possible sugar.[1]

Contents

Formation

Glycolaldehyde is an intermediate in the formose reaction.

Glycolaldehyde forms from many precursors, including the amino acid glycine. It can form by action of ketolase on fructose 1,6-bisphosphate in an alternate glycolysis pathway. This compound is transferred by thiamine pyrophosphate during the pentose phosphate shunt.

In purine catabolism, xanthine is first converted to urate. This is converted to 5-hydroxyisourate, which decarboxylates to allantoin and allantoic acid. After hydrolyzing one urea, this leaves glycolureate. After hydrolyzing the second urea, glycolaldehyde is left. Two glycolaldehydes condense to form erythrose 4-phosphate, which goes to the pentose phosphate shunt again.

In the media

Glycolaldehyde was identified in a giant cloud of gas and dust near the center of our own Milky Way Galaxy[2] and recently also in a star-forming region.[3]

Notes

  1. ^ Marstokk, K.-M., & Møllendal, H. (1973). "Microwave Spectra of Isotopic Glycolaldehydes, Substitution Structure, Intramolecular Hydrogen Bond and Dipole Moment". J. Mol. Struct. 19: 259–270. http://folk.uio.no/haraldm/Publikasjoner_pdf/ArtiklerPDF_HM/A11_IsotopicGlycolaldehydes.pdf. 
  2. ^ Hollis, J.M., Lovas, F.J., & Jewell, P.R. (2000). "Interstellar Glycolaldehyde: The First Sugar". The Astrophysical Journal 540 (2): 107–110. Bibcode 2000ApJ...540L.107H. doi:10.1086/312881. http://astrobiology.gsfc.nasa.gov/pdf/2000%20ref/hollis_2000.pdf. 
  3. ^ Beltran, M. T.; Codella, C.; Viti, S.; Neri, R.; Cesaroni, R.; (11/2008). First detection of glycolaldehyde outside the Galactic Center. eprint arXiv:0811.3821. http://babbage.sissa.it/abs/0811.3821. 

External links