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- phenylpyruvic acid
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/06/29 14:29:42」(JST)
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Phenylpyruvic acid
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| Names |
| IUPAC name
2-Oxo-3-phenylpropanoic acid
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| Other names
Phenylpyruvate; 3-Phenylpyruvic acid; Keto-phenylpyruvate; beta-Phenylpyruvic acid
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| Identifiers |
|
CAS Number
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156-06-9 Y |
| ChEBI |
CHEBI:30851 N |
| ChemSpider |
972 N |
| Jmol 3D model |
Interactive image |
| PubChem |
997 |
InChI
-
InChI=1S/C9H8O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,11,12) N
Key: InChIKey=BTNMPGBKDVTSJY-UHFFFAOYSA-N N
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SMILES
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C1=CC=C(C=C1)CC(=O)C(=O)O
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| Properties |
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Chemical formula
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C9H8O3 |
| Molar mass |
164.16 g·mol−1 |
| Melting point |
155 °C (311 °F; 428 K) (decomposes) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| N verify (what is YN ?) |
| Infobox references |
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Phenylpyruvic acid is the organic compound with the formula C6H5CH2C(O)CO2H. It is a keto acid.
Contents
- 1 Occurrence and properties
- 2 Preparation
- 3 See also
- 4 References
Occurrence and properties
The compound exists in equilibrium with its E- and Z-enol tautomers. It is a product from the oxidative deamination of phenylalanine.
Preparation
It is prepared by condensation of benzaldehyde and glycine derivatives to give phenylazlactone, which is then hydrolyzed with acid- or base-catalysis.[1] It can also be synthesized from benzyl chloride by double carbonylation.[2][3]
See also
- Phenylpyruvate decarboxylase
- Phenylpyruvate tautomerase
- Phenylketonuria
References
- ^ Carpy, Alain J. M.; Haasbroek, Petrus P.; Oliver, Douglas W. "Phenylpyruvic acid derivatives as enzyme inhibitors: Therapeutic potential on macrophage migration inhibitory factor" Medicinal Chemistry Research 2004, volume 13, pp. 565-577.
- ^ Wolfram, Joachim. "Preparation of α-keto-carboxylic acids from acyl halides". Google Patents US4481368 & US4481369. Ethyl Corporation.
- ^ Werner Bertleff, Michael Roeper, & Xavier Sava (2007). "Carbonylation". Ullmann's Encyclopedia of Industrial Chemistry: pg.19. doi:10.1002/14356007.a05_217.pub2.
UpToDate Contents
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English Journal
- Characterisation of volatile and non-volatile metabolites in etiolated leaves of tea (Camellia sinensis) plants in the dark.
- Yang Z, Kobayashi E, Katsuno T, Asanuma T, Fujimori T, Ishikawa T, Tomomura M, Mochizuki K, Watase T, Nakamura Y, Watanabe N.SourceSouth China Botanical Garden, Chinese Academy of Sciences, Xingke Road 723, Tianhe District, Guangzhou 510650, China.
- Food chemistry.Food Chem.2012 Dec 15;135(4):2268-76. doi: 10.1016/j.foodchem.2012.07.066. Epub 2012 Jul 20.
- Aroma is an essential factor affecting the quality of tea (Camellia sinensis) products. While changes of volatile compounds during tea manufacturing have been intensively studied, the effect of environmental factors on volatile contents of fresh tea leaves has received less attention. We found that
- PMID 22980801
- De novo production of the flavonoid naringenin in engineered Saccharomyces cerevisiae.
- Koopman F, Beekwilder J, Crimi B, van Houwelingen A, Hall RD, Bosch D, van Maris AJ, Pronk JT, Daran JM.SourceDepartment of Biotechnology, Delft University of Technology, Julianalaan 67, 2628 BC, Delft, the Netherlands. j.g.daran@tudelft.nl.
- Microbial cell factories.Microb Cell Fact.2012 Dec 8;11:155. doi: 10.1186/1475-2859-11-155.
- ABSTRACT:BACKGROUND: Flavonoids comprise a large family of secondary plant metabolic intermediates that exhibit a wide variety of antioxidant and human health-related properties. Plant production of flavonoids is limited by the low productivity and the complexity of the recovered flavonoids. Thus to
- PMID 23216753
- A standard numbering scheme for thiamine diphosphate-dependent decarboxylases.
- Vogel C, Widmann M, Pohl M, Pleiss J.SourceInstitute of Technical Biochemistry, University of Stuttgart, Allmandring 31, Stuttgart, 70569, Germany. juergen.pleiss@itb.uni-stuttgart.de.
- BMC biochemistry.BMC Biochem.2012 Nov 17;13:24. doi: 10.1186/1471-2091-13-24.
- ABSTRACT:BACKGROUND: Standard numbering schemes for families of homologous proteins allow for the unambiguous identification of functionally and structurally relevant residues, to communicate results on mutations, and to systematically analyse sequence-function relationships in protein families. Sta
- PMID 23157214
Japanese Journal
- Differential Resuscitative Effect of Pyruvate and its Analogues on VBNC (Viable But Non-Culturable) Salmonella
- Characterization of D-Lactate Dehydrogenase Producing D-3-Phenyllactic Acid from Pediococcus pentosaceus
- Bioscience, biotechnology, and biochemistry 76(4), 853-855, 2012-04-23
- NAID 10030752274
- Effect of L-Serine on the Biosynthesis of Aromatic Amino Acids in Escherichia coli
- Journal of nutritional science and vitaminology 52(4), 256-260, 2006-08
- NAID 110004789053
Related Links
- Phenylpyruvate; 3-Phenylpyruvic acid; Keto-phenylpyruvate; beta-Phenylpyruvic acid. Identifiers. CAS number · 156-06-9 · PubChem · 997 · Jmol-3D images, Image 1 · SMILES. C1=CC=C(C=C1)CC(=O)C(=O)O. Properties. Molecular formula ...
- In enzymology, a phenylpyruvate decarboxylase (EC 4.1.1.43) is an enzyme that catalyzes the chemical reaction. phenylpyruvate \ ... Hence, this enzyme has one substrate, phenylpyruvate, and two products, phenylacetaldehyde and CO2.
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