Global InformationPhenylglyoxal information
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| Names | |
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| Preferred IUPAC name
2-Oxo-2-phenylacetaldehyde | |
| Systematic IUPAC name
2-Oxo-2-phenylethanal | |
| Other names
Phenylglyoxal
1-Phenylethanedione | |
| Identifiers | |
CAS Number
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3D model (JSmol)
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| ChEMBL |
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| ChemSpider |
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| ECHA InfoCard | 100.012.761 |
| EC Number |
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PubChem CID
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CompTox Dashboard (EPA)
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InChI
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SMILES
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| Properties | |
Chemical formula
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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) |
Solubility in water
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forms the hydrate |
| Solubility in other solvents | common organic solvents |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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toxic |
| GHS labelling:[1] | |
Pictograms
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Signal word
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Warning |
Hazard statements
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H302, H315, H319, H335 |
Precautionary statements
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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
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3,4-Dihydroxyphenylacetaldehyde Methylglyoxal |
Related compounds
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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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Infobox references
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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]
- ^ "Phenylglyoxal". pubchem.ncbi.nlm.nih.gov. Retrieved 27 December 2021.
- ^ 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.
- ^ 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.
- ^ 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.