Glycolaldehyde

Glycolaldehyde

Names
IUPAC name 2-hydroxyacetaldehyde
Systematic IUPAC name 2-hydroxyethanal
Identifiers
CAS Number	141-46-8 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:17071 Y
ChemSpider	736 Y
ECHA InfoCard	100.004.987
KEGG	C00266 Y
PubChem	756
InChI InChI=1S/C2H4O2/c3-1-2-4/h1,4H,2H2 Y Key: WGCNASOHLSPBMP-UHFFFAOYSA-N Y InChI=1/C2H4O2/c3-1-2-4/h1,4H,2H2 Key: WGCNASOHLSPBMP-UHFFFAOYAH
SMILES O=CCO
Properties
Chemical formula	C2H4O2
Molar mass	60.052 g/mol
Density	1.065 g/mL
Melting point	97 °C (207 °F; 370 K)
Boiling point	131.3 °C (268.3 °F; 404.4 K)
Related compounds
Related aldehydes	3-Hydroxybutanal Lactaldehyde
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Lactaldehyde

Glycolaldehyde is the organic compound with the formula HOCH₂-CHO. It is the smallest possible molecule that contains both an aldehyde group and a hydroxyl group. It is a highly reactive molecule that occurs both in the biosphere and in the interstellar medium. It is normally supplied as a white solid.

Glycolaldehyde exists as depicted above as a gas. As a solid and molten liquid, it exists as a dimer. In aqueous solution, it exists as a mixture of at least four species, which rapidly interconvert.

It is the only possible diose, a 2-carbon monosaccharide, although a diose is not strictly a saccharide. While not a true sugar, it is the simplest sugar-related molecule.

Glycolaldehyde is the second most abundant compound formed when preparing pyrolysis oil (up to 10% by weight).

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.