- 関
- phenylpyruvate
WordNet
- street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
- any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
- having the characteristics of an acid; "an acid reaction"
PrepTutorEJDIC
- 酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2016/07/16 17:28:53」(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
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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 |
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
- Production of phenylpyruvic acid from L-phenylalanine using an L-amino acid deaminase from Proteus mirabilis: comparison of enzymatic and whole-cell biotransformation approaches.
- Hou Y1,2, Hossain GS1,2, Li J1,2, Shin HD3, Liu L4,5, Du G6,7.
- Applied microbiology and biotechnology.Appl Microbiol Biotechnol.2015 Oct;99(20):8391-402. doi: 10.1007/s00253-015-6757-0. Epub 2015 Jun 25.
- Phenylpyruvic acid (PPA) is an important organic acid that has a wide range of applications. In this study, the membrane-bound L-amino acid deaminase (L-AAD) gene from Proteus mirabilis KCTC 2566 was expressed in Escherichia coli BL21(DE3) and then the L-AAD was purified. After that, we used the pur
- PMID 26109004
- A GC/MS-based metabolomic approach for reliable diagnosis of phenylketonuria.
- Xiong X1, Sheng X1, Liu D1, Zeng T1, Peng Y1, Wang Y2.
- Analytical and bioanalytical chemistry.Anal Bioanal Chem.2015 Sep 26. [Epub ahead of print]
- Although the phenylalanine/tyrosine ratio in blood has been the gold standard for diagnosis of phenylketonuria (PKU), the disadvantages of invasive sample collection and false positive error limited the application of this discriminator in the diagnosis of PKU to some extent. The aim of this study w
- PMID 26410738
- Production of optically pure L-phenyllactic acid by using engineered Escherichia coli coexpressing L-lactate dehydrogenase and formate dehydrogenase.
- Zheng Z1, Zhao M2, Zang Y2, Zhou Y2, Ouyang J3.
- Journal of biotechnology.J Biotechnol.2015 Aug 10;207:47-51. doi: 10.1016/j.jbiotec.2015.05.015. Epub 2015 May 22.
- L-Phenyllactic acid (L-PLA) is a novel antiseptic agent with broad and effective antimicrobial activity. In addition, L-PLA has been used for synthesis of poly(phenyllactic acid)s, which exhibits better mechanical properties than poly(lactic acid)s. However, the concentration and optical purity of L
- PMID 26008622
Japanese Journal
- フェニルピルビン酸オキシムを基本骨格とする海洋生物由来の生物活性物質の化学
- 有機合成化学協会誌 : JOURNAL OF Synthetic Organic Chemistry JAPAN 63(6), 583-593, 2005-06-01
- NAID 10015675210
- Biogenesis of 2-Phenylethanol in Rose Flowers : Incorporation of [^2H_8]L-Phenylalanine into 2-Phenylethanol and its β-D-Glucopyranoside during the Flower Opening of Rosa 'Hoh-Jun' and Rosa damascena Mill.(Food & Nutrition Science)
- Bioscience, biotechnology, and biochemistry 66(5), 943-947, 2002-05-23
- NAID 110002693762
- <Abstract of Published Report>Polymorphism of Phenylpyruvic Acid Studied by IR, Raman and Solid State ^<13>C NMR Spectroscopy.
- 岐阜藥科大學紀要 = The annual proceedings of Gifu College of Pharmacy 49, 79, 2000-06-30
- NAID 120005563842
Related Links
- Sigma-Aldrich offers Aldrich-286958, Phenylpyruvic acid for your research needs. Find product specific information including CAS, MSDS, protocols and references. ... Packaging 5, 25 g in glass bottle Application Phenylpyruvic ...
- phenylpyruvic acid [fen″il-pi-roo´vik] an intermediate product of the metabolism of phenylalanine in the body. phe·nyl·py·ru·vic ac·id (fen'il-pī-rū'vik as'id), The transaminated product of the action of phenylalanine aminotransferase ...
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- 関
- phenylpyruvic acid
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4-ヒドロキシフェニルピルビン酸酸化酵素欠損症
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4-ヒドロキシフェニルピルビン酸