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286958

Sigma-Aldrich

Phenylpyruvic acid

98%

Synonym(s):

2-Oxo-3-phenylpropanoic acid, 2-Oxo-3-phenylpropionic acid

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About This Item

Linear Formula:
C6H5CH2COCOOH
CAS Number:
156-06-9
Molecular Weight:
164.16
Beilstein/REAXYS Number:
2207312
EC Number:
205-847-1
MDL number:
MFCD00002589
UNSPSC Code:
12352100
PubChem Substance ID:
24857257
NACRES:
NA.22

assay

98%

mp

150-154 °C (lit.)

storage temp.

−20°C

SMILES string

OC(=O)C(=O)Cc1ccccc1

InChI

1S/C9H8O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,11,12)

InChI key

BTNMPGBKDVTSJY-UHFFFAOYSA-N

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General description

Phenylpyruvic acid reduces glucose-6-phosphate dehydrogenase activity without pre-incubation.

Application

Phenylpyruvic acid was used in the synthesis of 3-phenyllactic acid (PLA) by lactate dehydrogenase.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Shuhuai Yu et al.
Biotechnology letters, 36(3), 627-631 (2013-11-20)
3-Phenyllactic acid (PLA) is an antimicrobial compound with broad and effective antimicrobial activity against both bacteria and fungi. Enzymatic production of PLA can be carried out from phenylpyruvic acid by lactate dehydrogenase (LDH); however, the enzymatic reaction is accompanied by
Hajer Ouertatani-Sakouhi et al.
Journal of biomolecular screening, 15(4), 347-358 (2010-03-17)
Macrophage migration inhibitory factor (MIF) is a major mediator of innate immunity and inflammation and presents a potential therapeutic target for various inflammatory, infectious, and autoimmune diseases, including cancer. Although a number of inhibitors have been identified and designed based
Faqing Tang et al.
Clinical biochemistry, 44(8-9), 711-718 (2011-03-16)
To search for markers of nasopharyngeal carcinoma (NPC) for diagnosis. Using gas chromatography and mass spectrometry, we evaluated 51 serum metabolites in 49 NPC, 37 throat cancer patients and 40 healthy controls. High metabolites were selected and confirmed in NPC
Tapan Kanti Paine et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 13(21), 6073-6081 (2007-05-01)
Iron(II)-phenylpyruvate complexes of tetradentate tris(6-methyl-2-pyridylmethyl)amine (6-Me3-TPA) and tridentate benzyl bis(2-quinolinylmethyl)amine (Bn-BQA) were prepared to gain insight into C-C bond cleavage catalyzed by dioxygenase enzymes. The complexes we have prepared and characterized are [Fe(6-Me3-tpa)(prv)][BPh4] (1), [Fe2(6-Me3-tpa)2(pp)][(BPh4)2] (2), and [Fe2(6-Me3-tpa)2(2'-NO2-pp)][(BPh4)2] (3), [Fe(6-Me3-tpa)(pp-Me)][BPh4]
Satoshi Hirano et al.
The Journal of biological chemistry, 283(10), 6459-6466 (2008-01-04)
Violacein and the indolocarbazoles are naturally occurring bisindole products with various biological activities, including antitumor activity. Although these compounds have markedly different molecular skeletons, their biosynthetic pathways share the same intermediate "compound X," which is produced from L-tryptophan via indole-3-pyruvic
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