Glyceraldehyde

Glyceraldehyde

Names
Systematic IUPAC name 2,3-Dihydroxypropanal
Other names Glyceraldehyde Glyceric aldehyde Glyceral
Identifiers
CAS Number	56-82-6 (racemic) Y 453-17-8 (R) N 497-09-6 (S) N
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:5445 Y
ChEMBL	ChEMBL173813 Y
ChemSpider	731 Y
ECHA InfoCard	100.006.088
PubChem	751
UNII	DI19XSG16H (racemic) N 41A680M0WB (R) N GI7U82BL5A (S) N
InChI InChI=1S/C3H6O3/c4-1-3(6)2-5/h1,3,5-6H,2H2 Y Key: MNQZXJOMYWMBOU-UHFFFAOYSA-N Y InChI=1/C3H6O3/c4-1-3(6)2-5/h1,3,5-6H,2H2 Key: MNQZXJOMYWMBOU-UHFFFAOYAU
SMILES O=CC(O)CO OCC(O)C=O
Properties
Chemical formula	C3H6O3
Molar mass	90.08 g·mol−1
Density	1.455 g/cm3
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).
N  (what is YN ?)
Infobox references

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 glycerol and aldehyde, as glyceraldehyde is glycerol with one hydroxymethyl group oxidized to an aldehyde.

Glyceraldehyde has one chiral center and therefore exists as two different enantiomers with opposite optical rotation:

While the optical rotation of glyceraldehyde is (+) for R and (−) for L, this is not true for all monosaccharides. The stereochemical configuration can only be determined from 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-.