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]]