|Molar mass||90.08 g·mol−1|
|Melting point||145 °C (293 °F; 418 K)|
|Boiling point||140 to 150 at 0.8 mmHg|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|(: / ?)|
Glyceraldehyde (glyceral) is a triose monosaccharide with chemical formula C3H6O3. It is the simplest of all common aldoses. It is a sweet, colorless, crystalline solid that is an intermediate compound in carbohydrate metabolism. The word comes from combining glycerine and aldehyde, as glyceraldehyde is merely glycerine with one hydroxymethylene group changed to an aldehyde.
- Structure 1
- Nomenclature 2
- Synthesis and biochemical role 3
- See also 4
- References 5
- R from Latin Rectus meaning "right", or
- S from Latin sinister meaning "left"
While the optical rotation of glyceraldehyde is (+) for R and (−) for S, this is not true for all monosaccharides. The stereochemical rotation can only be determined by the chemical structure, whereas the optical rotation can only be determined empirically (by experiment).
It was by a lucky guess that the molecular d- geometry was assigned to (+)-glyceraldehyde in the late 19th century, as confirmed by X-ray crystallography in 1951.
In the d/l system, glyceraldehyde is used as the configurational standard for carbohydrates. Monosaccharides with an absolute configuration identical to (R)-glyceraldehyde at the last stereocentre, for example C5 in glucose, are assigned the stereo-descriptor d-. Those similar to (S)-glyceraldehyde are assigned an l-.
Synthesis and biochemical role
Glyceraldehyde can be prepared, along with dihydroxyacetone, by the mild oxidation of glycerol, for example with hydrogen peroxide and a ferrous salt as catalyst. Dihydroxyacetone, the simplest ketose, is an isomer of glyceraldehyde. Interconversion of the phosphates of these two compounds, catalyzed by the enzyme triosephosphate isomerase, is an important intermediate step in glycolysis.
- Merck Index, 11th Edition, 4376