Glyceraldehyde
375136
225975875
2008-07-16T08:08:29Z
VolkovBot
3035831
robot Adding: [[pl:Aldehyd glicerynowy]]
{{Chembox new
| Name = Glyceraldehyde
| ImageFile = Glyceraldehyde-2D-skeletal.png
<!-- | ImageSize = 200px -->
| ImageName = Glyceraldehyde
| ImageFile1 = L-glyceraldehyde-2D-Fischer.png
<!-- | ImageSize1 = 100px -->
| ImageName1 = L-glyceraldehyde
| IUPACName = 2,3-Dihydroxypropanal
| OtherNames = Glyceraldehyde<br />Glyceric aldehyde
| ImageFile = L-glyceraldehyde-2D-skeletal.png
<!-- | ImageSize = 150px -->
| ImageName = L-glyceraldehyde
| Section1 = {{Chembox Identifiers
| CASNo = 367-47-5
| SMILES = OCC(O)C=O
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>3</sub>H<sub>6</sub>O<sub>3</sub>
| MolarMass = 90.08 g/mol
| Density = 1.455 g/cm³
| MeltingPt = 145 °C
| BoilingPt = 140-150 °C at 0.8 mmHg
}}
}}
'''Glyceraldehyde''' is a [[triose]] [[monosaccharide]] with [[chemical formula]] [[Carbon|C]]<sub>3</sub>[[Hydrogen|H]]<sub>6</sub>[[Oxygen|O]]<sub>3</sub>. It is the simplest of all common [[aldose]]s. It is a [[sweet]] colorless [[crystal]]line [[solid]] that is an intermediate compound in [[carbohydrate]] [[metabolism]]. The word comes from combining [[glycerine]] and [[aldehyde]], as glyceraldehyde is merely glycerine with one [[hydroxide]] changed to an aldehyde.
Glyceraldehyde has a [[chirality (chemistry)|chiral]] center and therefore exists as two different [[enantiomer]]s with opposite optical rotation:
* ''R'' from Latin ''rectus'' meaning ''right'', or
* ''S'' from Latin ''sinister'' meaning ''left''
{| class="wikitable" style="margin: 1em auto 1em auto"
|-
|align="center"| '''Name of [[enantiomer]]'''
|align="center"| '''<small>D</small>-glyceraldehyde'''<br>(''R'')-glyceraldehyde<br>(+)-glyceraldehyde
|align="center"| '''<small>L</small>-glyceraldehyde'''<br>(''S'')-glyceraldehyde<br>(−)-glyceraldehyde
|-
|align="center"| '''[[Fischer projection]]'''
|align="center"| [[Image:D-glyceraldehyde-2D-Fischer.png|80px|D-glyceraldehyde]]
|align="center"| [[Image:L-glyceraldehyde-2D-Fischer.png|100px|L-glyceraldehyde]]
|-
|align="center"| '''[[Skeletal formula]]'''
|align="center"| [[Image:D-glyceraldehyde-2D-skeletal.png|150px|D-glyceraldehyde]]
|align="center"| [[Image:L-glyceraldehyde-2D-skeletal.png|150px|L-glyceraldehyde]]
|-
|align="center"| '''[[Molecular model#Models based on ball-and-stick|Ball-and-stick model]]'''
|align="center"| [[Image:D-glyceraldehyde-3D-balls.png|150px|D-glyceraldehyde]]
|align="center"| [[Image:L-glyceraldehyde-3D-balls.png|150px|L-glyceraldehyde]]
|}
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).
Glyceraldehyde is used as the configurational standard for carbohydrates. Monosaccharides with an identical conformation at the last stereocentre, for example, C5 for [[glucose]], to (''R'')-glyceraldehyde are assigned the stereo-descriptor <small>D</small>, those similar to (''S'')-glyceraldehyde are assigned a <small>L</small>. Both, <small>D</small> and <small>L</small>, should be [[Small caps|small capital letters]].
Glyceraldehyde can be prepared, along with [[dihydroxyacetone]], by the mild oxidation of [[glycerol]], for example with [[hydrogen peroxide]] and a [[ferrous]] [[salt]] as [[catalyst]].
It was by a lucky guess that the <small>D</small> molecular geometry was assigned to (+)-glyceraldehyde in the late 19th century, as confirmed by [[x-ray crystallography]] in 1951.
== See also ==
* [[Stereoisomerism]]
==References==
*''Merck Index'', 11th Edition, '''4376'''.
== Further reading ==
* [http://www.sinica.edu.tw/~ccswww/zj-BI-1999-P.283.pdf Chin. Chem. Soc., Vol. 48(9) 283 (1999)] ''On the Assignment of Anomeric Configuration'' (pdf)
{{Carbohydrates}}
[[Category:Alcohols]]
[[Category:Aldehydes]]
[[Category:Monosaccharides]]
[[de:Glycerinaldehyd]]
[[es:Gliceraldehído]]
[[fr:Glycéraldéhyde]]
[[it:Gliceraldeide]]
[[lv:Glicerīnaldehīds]]
[[nl:Glyceraldehyde]]
[[ja:グリセルアルデヒド]]
[[pl:Aldehyd glicerynowy]]
[[ru:Глицераль]]
[[zh:甘油醛]]