“Phenylglyoxylic acid”的意思、由来-开放百科全书

词条

Phenylglyoxylic acid

释义

References

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 374826361
| ImageFile =Phenylglyoxalic acid.png
| ImageSize =
| IUPACName =2-Oxo-2-phenylacetic acid
| OtherNames =Benzoyl formate
Phenylglyoxalic acid
Phenylglyoxylate
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo =611-73-4
| PubChem =11915
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 18280
| SMILES =C1=CC=C(C=C1)C(=O)C(=O)O
| EINECS = 210-278-7
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 11421
| InChI = 1/C8H6O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5H,(H,10,11)
| InChIKey = FAQJJMHZNSSFSM-UHFFFAOYAS
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C8H6O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5H,(H,10,11)
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = FAQJJMHZNSSFSM-UHFFFAOYSA-N
| RTECS =
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C02137
|Section2={{Chembox Properties
| Formula =C₈H₆O₃
| MolarMass =150.13 g/mol
| Appearance =colorless solid
| Density =
| MeltingPtC = 64 to 66
| MeltingPt_notes =
| BoilingPt =
| Solubility =
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}

Phenylglyoxylic acid is the organic compound with the formula C₆H₅C(O)CO₂H. The conjugate base, known as benzoylformate is the substrate of benzoylformate decarboxylase, a thiamine diphosphate-dependent enzyme:

benzoylformate + H⁺ {{eqm}} benzaldehyde + CO₂

It is a colourless solid, m.p. 64–66 °C with a moderate acidity,which pKa=2.15.

Phenylglyoxylic acid can be synthesized by oxidation of mandelic acid with potassium permanganate.^[1] An alternative synthesis involves hydrolysis of benzoyl cyanide.^[2]

References

1. ^{{OrgSynth |author= B. B. Corson, Ruth A. Dodge, S. A. Harris, and R. K. Hazen |title= Ethyl Benzoylformate |collvol= 1 |collvolpages= 241| year= 1941 |prep= CV1P0241}}
2. ^{{OrgSynth |author= T. S. Oakwood and C. A. Weisgerber |title= Benzoylformic Acid |collvol= 3 |collvolpages= 114| year= 1955 |prep= cv3p0114}}

2 : Carboxylic acids|Phenyl compounds

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