286958

Sigma-Aldrich

Phenylpyruvic acid

98%

Synonym(s):
2-Oxo-3-phenylpropionic acid, 2-Oxo-3-phenylpropanoic acid
Linear Formula:
C6H5CH2COCOOH
CAS Number:
Molecular Weight:
164.16
Beilstein/REAXYS Number:
2207312
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

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.

Packaging

5, 25 g in glass bottle

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 286958.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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...
Joo Won Park et al.
Experimental & molecular medicine, 42(2), 105-115 (2009-12-01)
Phenylketonuria is an autosomal recessive disorder caused by a deficiency of phenylalanine hydroxylase. Transthyretin has been implicated as an indicator of nutritional status in phenylketonuria patients. In this study, we report that phenylalanine and its metabolite, phenylpyruvic acid, affect MAPK...
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...
Taiki Fujii et al.
Biochimica et biophysica acta, 1814(12), 1669-1676 (2011-06-16)
We discovered the phenyllactate (PLA)-producing fungal strain Wickerhamia fluorescens TK1 and purified phenylpyruvate reductase (PPR) from fungal cell-free extracts. The PPR used both NADPH and NADH as cofactors with more preference for the former. The enzyme reaction as well as...
Andrea Pereira Rosa et al.
Cellular and molecular neurobiology, 32(7), 1113-1118 (2012-04-06)
Phenylketonuria is a recessive autosomal disorder that is caused by a deficiency in the activity of phenylalanine-4-hydroxylase, which converts phenylalanine to tyrosine, leading to the accumulation of phenylalanine and its metabolites phenyllactic acid, phenylacetic acid, and phenylpyruvic acid in the...

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