| Revision as of 16:04, 21 January 2012 editThe chemistds (talk | contribs)Extended confirmed users5,761 edits changed CAS number after looking at Common Chemistry site← Previous edit |
Latest revision as of 23:15, 16 December 2024 edit undoArthurfragoso (talk | contribs)Extended confirmed users, Template editors4,591 edits Fixes images on dark mode |
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{{chembox |
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{{Chembox |
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| verifiedrevid = 442367318 |
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| verifiedrevid = 477396994 |
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| Name = Glyceraldehyde |
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| Name = Glyceraldehyde |
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| ImageFile = Glyceraldehyde-2D-skeletal.png |
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| ImageFile = Glyceraldehyde v2.svg |
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| ImageSize = 150px |
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| ImageSize = 150px |
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| ImageName = Glyceraldehyde |
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| ImageName = Glyceraldehyde |
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| ImageClass = skin-invert |
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| ImageFile1 = D-glyceraldehyde-2D-Fischer.png |
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| ImageFile1 = D-Glyceraldehyde 2D Fischer.svg |
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| ImageSize1 = 100px |
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| ImageName1 = D-glyceraldehyde |
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| ImageSize1 = 100px |
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| ImageName1 = D-glyceraldehyde |
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| ImageClass1 = skin-invert |
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| IUPACName = 2,3-Dihydroxypropanal |
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| OtherNames = Glyceraldehyde<br />Glyceric aldehyde |
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| IUPACName = Glyceraldehyde |
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| SystematicName = 2,3-Dihydroxypropanal |
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| Section1 = {{Chembox Identifiers |
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| OtherNames = Glyceraldehyde<br />Glyceric aldehyde<br/>Glyceral |
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| CASNo = 56-82-6 |
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|Section1={{Chembox Identifiers |
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| PubChem = 751 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| ChemSpiderID = 731 |
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| CASNo =56-82-6 |
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| SMILES = O=CC(O)CO |
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| CASNo_Comment = (racemic) |
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| InChI = 1/C3H6O3/c4-1-3(6)2-5/h1,3,5-6H,2H2 |
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| CASNo1_Ref = {{cascite|correct|CAS}} |
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| InChIKey = MNQZXJOMYWMBOU-UHFFFAOYAU |
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| CASNo1 = 453-17-8 |
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| StdInChI = 1S/C3H6O3/c4-1-3(6)2-5/h1,3,5-6H,2H2 |
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| CASNo1_Comment = (R) |
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| StdInChIKey = MNQZXJOMYWMBOU-UHFFFAOYSA-N |
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| CASNo2_Ref = {{cascite|correct|CAS}} |
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| SMILES = OCC(O)C=O |
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| CASNo2 = 497-09-6 |
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}} |
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| CASNo2_Comment = (S) |
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| Section2 = {{Chembox Properties |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| Reference=<ref>''Merck Index'', 11th Edition, '''4376'''</ref> |
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| UNII = DI19XSG16H |
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| C=3|H=6|O=3 |
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| UNII_Comment = (racemic) |
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| Density = 1.455 g/cm³ |
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| UNII1_Ref = {{fdacite|correct|FDA}} |
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| MeltingPtC = 145 |
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| UNII1 = 41A680M0WB |
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| BoilingPt = 140−150 °C at 0.8 mmHg |
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| UNII1_Comment = (R) |
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}} |
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| UNII2_Ref = {{fdacite|correct|FDA}} |
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| UNII2 = GI7U82BL5A |
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| UNII2_Comment = (S) |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = |
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| PubChem = 751 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 731 |
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| SMILES = O=CC(O)CO |
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| InChI = 1/C3H6O3/c4-1-3(6)2-5/h1,3,5-6H,2H2 |
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| InChIKey = MNQZXJOMYWMBOU-UHFFFAOYAU |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C3H6O3/c4-1-3(6)2-5/h1,3,5-6H,2H2 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = MNQZXJOMYWMBOU-UHFFFAOYSA-N |
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| SMILES2 = OCC(O)C=O |
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}} |
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|Section2={{Chembox Properties |
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| Properties_ref = <ref>''Merck Index'', 11th Edition, '''4376'''</ref> |
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| C=3 | H=6 | O=3 |
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| Density = 1.455 g/cm<sup>3</sup> |
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| MeltingPtC = 145 |
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| BoilingPtC = 140 to 150 |
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| BoilingPt_notes = at 0.8 mmHg |
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}} |
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}} |
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}} |
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'''Glyceraldehyde''' is a ] ] with ] ]<sub>3</sub>]<sub>6</sub>]<sub>3</sub>. It is the simplest of all common ]s. It is a ], colorless, ]line ] that is an intermediate compound in ] ]. The word comes from combining ] and ], as glyceraldehyde is merely glycerine with one hydroxymethylene group changed to an aldehyde. |
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'''Glyceraldehyde''' ('''glyceral''') is a ] ] with ] ]<sub>3</sub>]<sub>6</sub>]<sub>3</sub>. It is the simplest of all common ]s. It is a ], colorless, ]line ] that is an intermediate compound in ] ]. The word comes from combining ] and ], as glyceraldehyde is glycerol with one ] oxidized to an aldehyde. |
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== Structure == |
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== Structure == |
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Glyceraldehyde has ] center and therefore exists as two different ]s with opposite optical rotation: |
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Glyceraldehyde has one ] center and therefore exists as two different ]s with opposite optical rotation: |
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* In the ], either {{smallcaps all|D}} from Latin ''Dexter'' meaning "right", or {{smallcaps all|L}} from Latin ''Laevo'' meaning "left" |
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* ''R'' from Latin ''rectus'' meaning "right", or |
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* ''S'' from Latin ''sinister'' meaning "left" |
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* In the ], either R from Latin ''Rectus'' meaning "right", or S from Latin ''Sinister'' meaning "left" |
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{| class="wikitable" style="margin: 1em auto 1em auto" |
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{| class="wikitable" style="margin: 1em auto 1em auto" |
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|align="center"| '''{{smallcaps|d}}-glyceraldehyde'''<br>(''R'')-glyceraldehyde<br>(+)-glyceraldehyde |
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| align="center"| '''{{smallcaps all|D}}-glyceraldehyde'''<br />(''R'')-glyceraldehyde<br />(+)-glyceraldehyde |
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|align="center"| '''{{smallcaps|l}}-glyceraldehyde'''<br>(''S'')-glyceraldehyde<br>(−)-glyceraldehyde |
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| align="center"| '''{{smallcaps all|L}}-glyceraldehyde'''<br />(''S'')-glyceraldehyde<br />(−)-glyceraldehyde |
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|align="center"| ''']''' |
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| align = "center"| ''']''' |
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|align="center"| ] |
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|align="center"| ] |
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|align="center"| ''']''' |
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| align = "center"| ''']''' |
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|align="center"| ] |
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|align="center"| ] |
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|align="center"| ''']''' |
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| align = "center"| ''']''' |
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|align="center"| ] |
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|align="center"| ] |
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While the ] 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 ] (by experiment).<br /> |
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While the ] of glyceraldehyde is (+) for ''R'' and (−) for ''S'', 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 ] (by experiment). |
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It was by a lucky guess that the molecular {{smallcaps|d-}} geometry was assigned to (+)-glyceraldehyde in the late 19th century, as confirmed by ] in 1951. |
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It was by a lucky guess that the molecular {{smallcaps all|D-}} geometry was assigned to (+)-glyceraldehyde in the late 19th century, as confirmed by ] in 1951.<ref>{{cite journal | doi = 10.1038/168271a0 | title = Determination of the Absolute Configuration of Optically Active Compounds by Means of X-Rays | date = 1951 | last1 = Bijvoet | first1 = J. M. | last2 = Peerdeman | first2 = A. F. | last3 = Van Bommel | first3 = A. J. | journal = Nature | volume = 168 | issue = 4268 | pages = 271–272 | bibcode = 1951Natur.168..271B }}</ref> |
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== Nomenclature == |
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== Nomenclature == |
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In the ], glyceraldehyde is used as the configurational standard for carbohydrates.<ref>{{Cite web|date=2015-03-19|title=22.03: The D and L Notation|url=https://chem.libretexts.org/Courses/Purdue/Purdue%3A_Chem_26200%3A_Organic_Chemistry_II_(Wenthold)/Chapter_22._Carbohydrates/22.03%3A_The_D_and_L_Notation|access-date=2022-01-09|website=Chemistry LibreTexts|language=en}}</ref> Monosaccharides with an absolute configuration identical to (''R'')-glyceraldehyde at the ''last'' stereocentre, for example C5 in ], are assigned the stereo-descriptor {{smallcaps all|'''D-'''}}. Those similar to (''S'')-glyceraldehyde are assigned an {{smallcaps all|'''L-'''}}. <!---Both {{smallcaps all|D}} and {{smallcaps all|L}}, should be ].---> |
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== Chemical synthesis == |
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In the ], glyceraldehyde is used as the configurational standard for carbohydrates. Monosaccharides with a conformation identical to (''R'')-glyceraldehyde at the last stereocentre, for example C5 in ], are assigned the stereo-descriptor {{smallcaps|'''d-'''}}. Those similar to (''S'')-glyceraldehyde are assigned an {{smallcaps|'''l-'''}}. <!---Both {{smallcaps|d}} and {{smallcaps|l}}, should be ].---> |
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Glyceraldehyde can be prepared, along with ], by the mild oxidation of ], for example with ]<ref>{{Cite journal|last1=Wu|first1=Gongde|last2=Wang|first2=Xiaoli|last3=Jiang|first3=Taineng|last4=Lin|first4=Qibo|date=2015-11-27|title=Selective Oxidation of Glycerol with 3% H2O2 Catalyzed by LDH-Hosted Cr(III) Complex|journal=Catalysts|language=en|volume=5|issue=4|pages=2039–2051|doi=10.3390/catal5042039|issn=2073-4344|doi-access=free}}</ref> and a ] ] as ].{{Citation needed|date=January 2022}} |
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Its cyclohexylidene acetal can also be produced by oxidative cleavage of the bis(acetal) of ].<ref>{{cite journal |doi=10.15227/orgsyn.099.0363|title=Preparation of 1,2:5,6-Di-O-cyclohexylidene-D-mannitol and 2,3-Cyclohexylidene-D-glyceraldehyde |year=2022 |last1=Dhatrak |first1=N. R. |last2= Jagtap |first2=T. N.|last3= Shinde|first3=A. B. |journal=Organic Syntheses |volume=99 |pages=363–380 |s2cid=254320929 |doi-access=free }}</ref> |
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== Synthesis and biochemical role == |
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== Biochemistry == |
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Glyceraldehyde can be prepared, along with ], by the mild oxidation of ], for example with ] and a ] ] as ]. Dihydroxyacetone, the simplest ], is an ] of glyceraldehyde. Interconversion of the phosphates of these two compounds, catalyzed by the ] ], is an important intermediate step in ]. |
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The enzyme ] has two substrates, ] and ], and 3 products, D-glyceraldehyde, ] and ].<ref>{{Cite journal|last1=Kormann|first1=Alfred W.|last2=Hurst|first2=Robert O.|last3=Flynn|first3=T.G.|title=Purification and properties of an NADP+-dependent glycerol dehydrogenase from rabbit skeletal muscle|url=https://linkinghub.elsevier.com/retrieve/pii/0005274472909655|journal=Biochimica et Biophysica Acta (BBA) - Enzymology|year=1972|language=en|volume=258|issue=1|pages=40–55|doi=10.1016/0005-2744(72)90965-5|pmid=4400494}}</ref> |
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The interconversion of the phosphates of glyceraldehyde (]) and ] (]), catalyzed by the ] ], is an intermediate step in ]. |
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== See also == |
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== See also == |
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==References== |
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==References== |
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{{reflist}} |
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{{Reflist}} |
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{{Carbohydrates}} |
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{{Carbohydrates}} |
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{{Fructose and galactose metabolic intermediates}} |
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{{Fructose and galactose metabolic intermediates}} |
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{{Authority control}} |
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