Phenylglyoxal

Phenylglyoxal
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
2-Oxo-2-phenylacetaldehyde
Systematic IUPAC name
2-Oxo-2-phenylethanal
Other names
Phenylglyoxal
1-Phenylethanedione
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.012.761 Edit this at Wikidata
EC Number
  • 214-036-1
RTECS number
  • KM5775180
UNII
  • InChI=1S/C8H6O2/c9-6-8(10)7-4-2-1-3-5-7/h1-6H ☒N
    Key: OJUGVDODNPJEEC-UHFFFAOYSA-N ☒N
  • InChI=1/C8H6O2/c9-6-8(10)7-4-2-1-3-5-7/h1-6H
    Key: OJUGVDODNPJEEC-UHFFFAOYAA
  • O=C(C=O)c1ccccc1
Properties
C8H6O2
Molar mass 134.13 g/mol (anhydrous)
Appearance yellow liquid (anhydrous)
white crystals (hydrate)
Density ? g/cm3
Melting point 76 to 79 °C (169 to 174 °F; 349 to 352 K) (hydrate)
Boiling point 63 to 65 °C (145 to 149 °F; 336 to 338 K) (0.5 mmHg, anhydrous)
forms the hydrate
Solubility in other solvents common organic solvents
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 toxic
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H302, H315, H319, H335
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
Related compounds
Related aldehydes
 3,4-Dihydroxyphenylacetaldehyde

Methylglyoxal
Phenylacetaldehyde

Related compounds
 benzil
glyoxal
acetophenone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[2] It has also been used to attach chemical payload (probes) to the amino acid citrulline[3] and to peptides/proteins.[4]

  1. ^ "Phenylglyoxal". pubchem.ncbi.nlm.nih.gov. Retrieved 27 December 2021.
  2. ^ Kenji Takahashi (1968). "The Reaction of Phenylglyoxal with Arginine Residues in Proteins". J. Biol. Chem. 243 (23): 6171–9. doi:10.1016/S0021-9258(18)94475-3. PMID 5723461.
  3. ^ Bicker KL, Subramanian V, Chumanevich AA, Hofseth LJ, Thompson PR (2012). "Seeing citrulline: development of a phenylglyoxal-based probe to visualize protein citrullination". J Am Chem Soc. 134 (41): 17015–8. doi:10.1021/ja308871v. PMC 3572846. PMID 23030787.
  4. ^ Thompson DA, Ng R, Dawson PE (2016). "Arginine selective reagents for ligation to peptides and proteins". J Pept Sci. 22 (5): 311–9. doi:10.1002/psc.2867. PMID 27005702. S2CID 35028264.