phenylglyoxal

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 444049232

| Name = Phenylglyoxal

| ImageFile = Phenylglyoxal.svg

| ImageName = Skeletal formula

| ImageFile1 = Phenylglyoxal-3D-balls.png

| ImageSize1 = 160px

| ImageName1 = Ball-and-stick model

| PIN = 2-Oxo-2-phenylacetaldehyde

| SystematicName = 2-Oxo-2-phenylethanal

| OtherNames = Phenylglyoxal
1-Phenylethanedione

|Section1={{Chembox Identifiers

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = N45G3015PA

| SMILES = O=C(C=O)c1ccccc1

| CASNo_Ref = {{cascite|changed|??}}

| CASNo = 1075-06-5

| CASNo_Comment = (monohydrate)

| CASNo2_Ref = {{cascite|correct|CAS}}

| 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

| C=8 | H=6 | O=2

| MolarMass = 134.13 g/mol (anhydrous)

| Appearance = yellow liquid (anhydrous)
white crystals (hydrate)

| Density = ? g/cm³

| Solubility = forms the hydrate

| Solvent = other solvents

| SolubleOther = common organic solvents

| MeltingPtC = 76 to 79

| MeltingPt_notes = (hydrate)

| BoilingPtC = 63 to 65

| BoilingPt_notes = (0.5 mmHg, anhydrous)

}}

|Section7={{Chembox Hazards

| ExternalSDS =

| MainHazards = toxic

| FlashPt =

| GHS_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}}

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|302|315|319|335}}

| 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 = 3,4-Dihydroxyphenylacetaldehyde

Methylglyoxal

Phenylacetaldehyde

| OtherCompounds = benzil
glyoxal
acetophenone

}}

}}

Phenylglyoxal is the organic compound with the formula C₆H₅C(O)C(O)H. It contains both an aldehyde and a ketone functional group. It is yellow liquid when anhydrous but readily forms a colorless crystalline hydrate. It has been used as a reagent to modify the amino acid, arginine.{{cite journal | title = The Reaction of Phenylglyoxal with Arginine Residues in Proteins | author = Kenji Takahashi | volume = 243 | issue = 23 | pages = 6171–9 | journal = J. Biol. Chem. | 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 }} It has also been used to attach chemical payload (probes) to the amino acid citrulline{{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}} and to peptides/proteins.{{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 }}