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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
Zhaojuan Zheng et al.
PloS one, 6(4), e19030-e19030 (2011-05-03)
Phenyllactic acid (PLA), a novel antimicrobial compound with broad and effective antimicrobial activity against both bacteria and fungi, can be produced by many microorganisms, especially lactic acid bacteria. However, the concentration and productivity of PLA have been low in previous
Paddy Jim Baggot et al.
Fetal diagnosis and therapy, 23(3), 245-248 (2008-04-18)
Organic acids were examined from normal and Down syndrome pregnancies to identify possible differences between the amniotic fluid from fetuses with Down Syndrome compared with that of normal fetuses. Amniotic fluids were obtained from prior amniocenteses. Forty-one normal and 22
Valeriano Dal Cin et al.
The Plant cell, 23(7), 2738-2753 (2011-07-14)
Altering expression of transcription factors can be an effective means to coordinately modulate entire metabolic pathways in plants. It can also provide useful information concerning the identities of genes that constitute metabolic networks. Here, we used ectopic expression of a
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]
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