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phenylglyoxal
Sign in to savePhenylglyoxal 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. It has also been used to attach chemical payload (probes) to the amino acid citrulline and to peptides/proteins.
Chemical data
- Formula
- C8H6O2
- Molecular weight
- 134.13 g/mol
- IUPAC name
- 2-oxo-2-phenylacetaldehyde
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
1,023 papers- Phenylglyoxal-based visualization of citrullinated proteins on Western blots.Molecules (Basel, Switzerland) · 2015
- Phenylglyoxal is not a selective inhibitor of phagocytosis.Journal of cell science · 1979
- Phenylglyoxal as a template site-specific reagent for DNA and RNA polymerases. Selective inhibition of initiation.The Journal of biological chemistry · 1980
- Phenylglyoxal modification of arginines in mammalian D-amino-acid oxidase.European journal of biochemistry · 1987
- Phenylglyoxal modification of the Photosystem II reaction center.Biochimica et biophysica acta · 1987
via PubMed
Wikidata facts
- Subclass of
- aldehydes
- Mass
- 134.037
Show 5 more facts
- chemical formula
- C₈H₆O₂
- canonical SMILES
- C1=CC=C(C=C1)C(=O)C=O
- Commons category
- Phenylglyoxal
- subject has role
- enzyme inhibitor
- found in taxon
- Escherichia coli
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Properties
- Preparation
- References
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. It has also been used to attach chemical payload (probes) to the amino acid citrulline and to peptides/proteins.
==Properties== Like some other aldehydes, phenylglyoxal polymerizes upon standing, as indicated by solidification of the liquid. Upon heating, this polymer "cracks" to give back the yellow aldehyde. Dissolution of phenylglyoxal in water gives crystals of the hydrate: C6H5C(O)COH + H2O → C6H5C(O)CH(OH)2 Upon heating, the hydrate loses water and regenerates the anhydrous liquid.
Excerpted from Wikipedia’s “phenylglyoxal” article, available under the CC BY-SA 4.0 licence.