Phenylpyruvic acid

Base Information

• Chemical Name: Phenylpyruvic acid
• CAS No.: 156-06-9
• Deprecated CAS: 1129287-56-4
• Molecular Formula: C9H8O3
• Molecular Weight: 164.161
• Hs Code.: 29183000
• European Community (EC) Number: 205-847-1
• UNII: X7CO62M413
• DSSTox Substance ID: DTXSID1042281
• Nikkaji Number: J11.025F
• Wikipedia: Phenylpyruvic_acid
• Wikidata: Q425030
• Metabolomics Workbench ID: 37133
• ChEMBL ID: CHEMBL1162488
• Mol file: 156-06-9.mol

Synonyms:3-phenylpyruvate;beta-phenylpyruvic acid;phenylpyruvate;phenylpyruvic acid;phenylpyruvic acid, calcium salt;phenylpyruvic acid, sodium salt

Chemical Property of Phenylpyruvic acid

Chemical Property:

• Vapor Pressure: 0.000546mmHg at 25°C
• Melting Point: 150-154 °C(lit.)
• Boiling Point: 299.1 °C at 760 mmHg
• PKA: 2.61±0.54(Predicted)
• Flash Point: 148.9 °C
• PSA: 54.37000
• Density: 1.257g/cm³
• LogP: 0.88280
• Storage Temp.: −20°C
• Sensitive.: Light & Air Sensitive & Hygrosco
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 164.047344113
• Heavy Atom Count: 12
• Complexity: 180

Purity/Quality:

99.5% ^*data from raw suppliers

α-OxobenzenepropanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Food Additives
• Canonical SMILES: C1=CC=C(C=C1)CC(=O)C(=O)O
• Uses: α-Oxobenzenepropanoic Acid is a useful reagent for organic synthesis.

Technology Process of Phenylpyruvic acid

There total 139 articles about Phenylpyruvic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

4-benzyl-4-hydroxy-3-phenylisoxazoline-5-one (80490-42-2) → 2-oxo-3-(phenyl)propionic acid (156-06-9) + benzonitrile (100-47-0)

Guidance literature:

With 2,6-dichloro-benzonitrile; In benzene; for 3h; Heating;

Reference yield: 92.7%

4-benzyl-4-hydroxy-3-methylisoxazoline-5-one (80490-52-4) → 2-oxo-3-(phenyl)propionic acid (156-06-9) + acetonitrile (75-05-8,26809-02-9)

Guidance literature:

With 2,6-dichloro-benzonitrile; In benzene; for 1h; Heating;

Reference yield: 84.0%

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → 2-oxo-3-(phenyl)propionic acid (156-06-9) + D-phenyllactic acid (828-01-3,7326-19-4,20312-36-1,156-05-8)

Guidance literature:

With formate dehydrogenase; oxygen; ammonium formate; NADH; In aq. phosphate buffer; at 21 ℃; for 7h; under 750.075 Torr; pH=7; Concentration; stereoselective reaction; Enzymatic reaction;

DOI:10.1002/chem.201403195

upstream raw materials:

3-phenyl-2-sulfanylpropenoic acid

formic acid

3,4-dioxo-5-phenyl-valeric acid

5-benzylidene-2-thioxo-oxazolidin-4-one

Downstream raw materials:

2-benzyl-3-cyano-2-hydroxy-3-phenyl-propionic acid

2-(N-acetylamino)cinnamic acid

2,3-diphenyl-[4,7]phenanthroline-1-carboxylic acid

3-methyl-2-phenyl-[4,7]phenanthroline-1-carboxylic acid

Refernces

• 1、 Zamir, Lolita O.,Tiberio, Robert,Jensen, Roy A.. "DIFFERENTIAL ACID-CATALYZED AROMATIZATION OF PREPHENATE, AROGENATE, AND SPIRO-AROGENATE". . p. 2815 - 2818. Retrieved 1983.
• 2、 Metzenberg,Mitchell. "". . p. 51,52. Retrieved 1956.
• 3、 Utsumi, Tomohiro,Arima, Jiro,Sakaguchi, Chika,Tamura, Takashi,Sasaki, Chiduko,Kusakabe, Hitoshi,Sugio, Shigetoshi,Inagaki, Kenji. "Arg305 of streptomyces l-glutamate oxidase plays a crucial role for substrate recognition". . p. 951 - 955. Retrieved 2012.
• 4、 Erlenmeyer Junior. "-". . p. 165. Retrieved 1892.
• 5、 Bihan, J. Y.-Le,Senechal-Tocquer, M.-C.,Senechal. D.,Gentric, D.,Caro, B.,et all.. "SYNTHESE DIRECTE DE PHENYLPYRUVATES CHROME TRICARBONYLE. INFLUENCES DE LA SUBSTITUTION SUR LA NATURE CETONIQUE OU ENOLIQUE DES PRODUITS ISOLES, ET DU GROUPEMENT Cr(CO)3 SUR L'EQUILIBRE TAUTOMERE.". . p. 3565 - 3574. Retrieved 1988.
• 6、 Goel, Anjali,Sharma, Shivani. "Mechanistic study of the oxidation of L-phenylalanine by hexacyanoferrate(III) catalyzed by iridium(III) in aqueous alkaline medium". . p. 549 - 554. Retrieved 2010.
• 7、 Haering, Dietmar,Distefano, Mark D. "Specific host-guest interactions in a protein-based artificial transaminase". . p. 2461 - 2466. Retrieved 2001.
• 8、 Huang, Junjie,Liang, Baihui,Chen, Xiuwen,Liu, Yifu,Li, Yawen,Liang, Jingwen,Zhu, Weidong,Tang, Xiaodong,Li, Yibiao,Zhu, Zhongzhi. "Rapid assembly of α-ketoamides through a decarboxylative strategy of isocyanates with α-oxocarboxylic acids under mild conditions". supporting information. p. 4783 - 4787. Retrieved 2021/06/11.
• 9、 Chen, Yanchun,Cui, Xuexian,Cui, Yinglu,Li, Chuijian,Li, Ruifeng,Li, Tao,Sun, Jinyuan,Wu, Bian,Zhu, Tong. "Exploration of Transaminase Diversity for the Oxidative Conversion of Natural Amino Acids into 2-Ketoacids and High-Value Chemicals". . p. 7950 - 7957. Retrieved 2020/08/21.