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Revision as of 12:22, 10 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'UNII').← Previous edit Latest revision as of 02:18, 7 December 2024 edit undoInnerstream (talk | contribs)Autopatrolled, Extended confirmed users4,071 editsmNo edit summary 
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{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 373991347
| Watchedfields = changed
⚫ | Name = Phenylglyoxal
⚫ | verifiedrevid = 444049232
⚫ | ImageFile = Phenylglyoxal.png
⚫ | Name = Phenylglyoxal
⚫ | ImageName = Skeletal formula
| ImageFile1 = Phenylglyoxal-3D-balls.png | ImageFile = Phenylglyoxal.svg
⚫ | ImageName = Skeletal formula
⚫ | ImageSize1 = 160px
⚫ | ImageFile1 = Phenylglyoxal-3D-balls.png
⚫ | ImageName1 = Ball-and-stick model
⚫ | ImageSize1 = 160px
| IUPACName = Phenylglyoxal
⚫ | ImageName1 = Ball-and-stick model
| OtherNames = oxo(phenyl)acetaldehyde, 1-phenylethanedione,
| PIN = 2-Oxo-2-phenylacetaldehyde
⚫ | Section1 = {{Chembox Identifiers
| SystematicName = 2-Oxo-2-phenylethanal
⚫ | UNII = N45G3015PA
| OtherNames = Phenylglyoxal<br/>1-Phenylethanedione
⚫ |Section1={{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | UNII = N45G3015PA
| SMILES = O=C(C=O)c1ccccc1 | SMILES = O=C(C=O)c1ccccc1
| CASNo_Ref = {{cascite|changed|??}}
| CASNo = 1075-06-5 | CASNo = 1075-06-5
| CASOther = (monohydrate)<br /> (anhydrous) | CASNo_Comment = (monohydrate)
| CASNo2_Ref = {{cascite|correct|CAS}}
⚫ | RTECS = KM5775180
| CASNo2 = 1074-12-0
| CASNo2_Comment = (anhydrous)
| ChEMBL = 233632
⚫ | RTECS = KM5775180
| PubChem = 14090
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 13470
| EC_number = 214-036-1
| InChI = 1/C8H6O2/c9-6-8(10)7-4-2-1-3-5-7/h1-6H
| InChIKey = OJUGVDODNPJEEC-UHFFFAOYAA
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C8H6O2/c9-6-8(10)7-4-2-1-3-5-7/h1-6H
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = OJUGVDODNPJEEC-UHFFFAOYSA-N
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=8| H=6 | O=2 | C=8 | H=6 | O=2
| MolarMass = 134.13 g/mol (anhydrous) | MolarMass = 134.13 g/mol (anhydrous)
| Appearance = yellow liquid (anhydrous)<br />white crystals (hydrate) | Appearance = yellow liquid (anhydrous)<br />white crystals (hydrate)
| Density = ? g/cm<sup>3</sup> | Density = ? g/cm<sup>3</sup>
| Solubility = forms the hydrate | Solubility = forms the hydrate
| Solvent = other solvents | Solvent = other solvents
| SolubleOther = common organic solvents | SolubleOther = common organic solvents
| MeltingPt = 76-79 °C (hydrate) | MeltingPtC = 76 to 79
| MeltingPt_notes = (hydrate)
⚫ | BoilingPt = 63–65° (0.5 mm, anhydrous)
| BoilingPtC = 63 to 65
⚫ }}
⚫ | BoilingPt_notes = (0.5 mmHg, anhydrous)
⚫ | Section7 = {{Chembox Hazards
⚫ }}
| ExternalMSDS =
⚫ |Section7={{Chembox Hazards
⚫ | MainHazards = toxic<!-- and tastes terrible-->
| FlashPt = | ExternalSDS =
⚫ | MainHazards = toxic<!-- and tastes terrible-->
| RPhrases = 22-36/37/38
| FlashPt =
| SPhrases = 22-26-36
| GHS_ref=<ref>{{cite web |title=Phenylglyoxal |url=https://pubchem.ncbi.nlm.nih.gov/compound/14090#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |access-date=27 December 2021 |language=en}}</ref>
⚫ }}
| GHSPictograms = {{GHS07}}
⚫ | Section8 = {{Chembox Related
| GHSSignalWord = Warning
⚫ | Function = aldehydes
| HPhrases = {{H-phrases|302|315|319|335}}
⚫ | OtherFunctn = ]<br />
| PPhrases = {{P-phrases|261|264|270|271|280|301+312|302+352|304+340|305+351+338|312|321|330|332+313|337+313|362|403+233|405|501}}
⚫ }}
⚫ |Section8={{Chembox Related
⚫ | OtherFunction_label = aldehydes
⚫ | OtherFunction = ]<br />
]<br /> ]<br />
] ]
| OtherCpds = ]<br />]<br />] | OtherCompounds = ]<br />]<br />]
}} }}
}} }}


'''Phenylglyoxal''' is the ] with the ] C<sub>6</sub>H<sub>5</sub>C(O)C(O)H. It contains both an ] and a ] ]. It is yellow liquid when anhydrous but readily forms a colorless crystalline hydrate. It has been used as a reagent to modify the ], ].<ref>{{cite journal | title = The Reaction of Phenylglyoxal with Arginine Residues in Proteins | author = Kenji Takahashi | volume = 243 | issue = 23 | pages = 6171 | journal = ] | url = http://www.jbc.org/cgi/content/abstract/243/23/6171 | pmid = 5723461 | year = 1968}}</ref> '''Phenylglyoxal''' is the ] with the ] C<sub>6</sub>H<sub>5</sub>C(O)C(O)H. It contains both an ] and a ] ]. It is yellow liquid when anhydrous but readily forms a colorless crystalline hydrate. It has been used as a reagent to modify the ], ].<ref>{{cite journal | title = The Reaction of Phenylglyoxal with Arginine Residues in Proteins | author = Kenji Takahashi | volume = 243 | issue = 23 | pages = 6171–9 | journal = ] | url = http://www.jbc.org/cgi/content/abstract/243/23/6171 | pmid = 5723461 | year = 1968| doi = 10.1016/S0021-9258(18)94475-3 | doi-access = free }}</ref> It has also been used to attach chemical payload (probes) to the amino acid citrulline<ref>{{cite journal | pmid = 23030787 | doi=10.1021/ja308871v | volume=134 | issue=41 | title=Seeing citrulline: development of a phenylglyoxal-based probe to visualize protein citrullination | pmc=3572846 | year=2012 | journal=J Am Chem Soc | pages=17015–8 | vauthors=Bicker KL, Subramanian V, Chumanevich AA, Hofseth LJ, Thompson PR}}</ref> and to peptides/proteins.<ref>{{cite journal | pmid = 27005702 | doi=10.1002/psc.2867 | volume=22 | issue=5 | title=Arginine selective reagents for ligation to peptides and proteins | year=2016 | journal=J Pept Sci | pages=311–9 | vauthors=Thompson DA, Ng R, Dawson PE| s2cid=35028264 }}</ref>


==Properties== ==Properties==
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==Preparation== ==Preparation==
Phenylglyoxal was first prepared by thermal decomposition of the ] derivative of the ]:<ref>{{cite journal | author = H. von Pechmann | title = Zur Spaltung der Isonitrosoverbindungen | journal = ] | year = 1887 | volume = 20 | pages = 2904–2906 | doi = 10.1002/cber.188702002156}}</ref> Phenylglyoxal was first prepared by thermal decomposition of the ] derivative of the ]:<ref>{{cite journal | author = H. von Pechmann | title = Zur Spaltung der Isonitrosoverbindungen | journal = ] | year = 1887 | volume = 20 | pages = 2904–2906 | doi = 10.1002/cber.188702002156 | issue = 2| url = https://zenodo.org/record/1425483 }}</ref>
: C<sub>6</sub>H<sub>5</sub>C(O)CH(NOSO<sub>2</sub>H) + 2 H<sub>2</sub>O → C<sub>6</sub>H<sub>5</sub>C(O)CHO + NH<sub>4</sub>HSO<sub>4</sub> : C<sub>6</sub>H<sub>5</sub>C(O)CH(NOSO<sub>2</sub>H) + 2 H<sub>2</sub>O → C<sub>6</sub>H<sub>5</sub>C(O)CHO + NH<sub>4</sub>HSO<sub>4</sub>
More conveniently, it can be prepared from ] by reaction with KCH<sub>2</sub>S(O)CH<sub>3</sub> to give PhC(O)CH(SCH<sub>3</sub>)(OH), which is oxidized with ].<ref>{{OrgSynth | author = Mikol, G. J.; Russell, G. A. | title = Phenylglyoxal | collvol = 5 | collvolpages = 937 | year = 1973 | prep = cv5p0937}}</ref> Alternatively, it can also be prepared by oxidation of ] with ].<ref>{{OrgSynth | author = Riley, H. A.; Gray, A. R. | title = Phenylglyoxal | collvol = 2 | collvolpages = 509 | year =1943 | prep = CV2P0509}}</ref> More conveniently, it can be prepared from ] by reaction with KCH<sub>2</sub>S(O)CH<sub>3</sub> to give PhC(O)CH(SCH<sub>3</sub>)(OH), which is oxidized with ].<ref>{{OrgSynth | author = Mikol, G. J. | author2 = Russell, G. A. | title = Phenylglyoxal | collvol = 5 | collvolpages = 937 | year = 1973 | prep = cv5p0937}}</ref> Alternatively, it can also be prepared by oxidation of ] with ].<ref>{{OrgSynth | author = Riley, H. A. | author2 = Gray, A. R. | title = Phenylglyoxal | collvol = 2 | collvolpages = 509 | year =1943 | prep = CV2P0509}}</ref>


==References== ==References==
{{reflist}} {{Reflist}}


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