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Merck
CN

114286

4-Hydroxyphenylpyruvic acid

98%

Synonym(s):

3-(4-Hydroxyphenyl)-2-oxopropanoic acid

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About This Item

Linear Formula:
HOC6H4CH2COCO2H
CAS Number:
156-39-8
Molecular Weight:
180.16
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24847164
EC Number:
205-852-9
Beilstein/REAXYS Number:
2691632
MDL number:
MFCD00002591

Key Documents

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Product Name

4-Hydroxyphenylpyruvic acid, 98%

InChI key

KKADPXVIOXHVKN-UHFFFAOYSA-N

InChI

1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13)

SMILES string

OC(=O)C(=O)Cc1ccc(O)cc1

assay

98%

form

solid

mp

219-220 °C (dec.) (lit.)

solubility

ethanol: soluble 50 mg/mL

functional group

carboxylic acid
ketone

Quality Level

100

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Related Categories

Application

<ul>
<li><strong>Identification of serum biomarkers of ischemic stroke:</strong>4-Hydroxyphenylpyruvic acid is used as a potential diagnostic biomarker in the study to distinguish hypertensive ischemic stroke (IS) patients from both healthy individuals and those with hypertension (Zhao et al., 2023).</li>
</ul>

General description

4-hydroxyphenylpyruvic acid can be determined in pork meat and Iberian ham samples by a sensitive method of multiple reaction monitoring (MRM) by mass spectrometry.

Preparation Note

50 gm of 4-Hydroxyphenylpyruvic acid dissolves in 1 mL of ethanol to yield a clear, light yellow solution.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN6358
BCCM8624
BCCM6509
BCCL0033
BCCJ5422

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Francisco J Hidalgo et al.
Food chemistry, 140(1-2), 183-188 (2013-04-13)
An analytical method which offers accurate determination and identification of eight α-keto acids (α-ketoglutaric acid, pyruvic acid, 4-hydroxyphenylpyruvic acid, 3-methyl-2-oxobutyric acid, α-keto-γ-methylthiobutyric acid, 4-methyl-2-oxovaleric acid, 3-methyl-2-oxovaleric acid, and phenylpyruvic acid) in pork meat and Iberian ham samples is reported. The
Ute Metzger et al.
Journal of molecular biology, 404(4), 611-626 (2010-10-16)
CloQ is an aromatic prenyltransferase from the clorobiocin biosynthetic pathway of Streptomyces roseochromogenes var. oscitans. It is involved in the synthesis of the prenylated hydroxybenzoate moiety of the antibiotic, specifically catalyzing the attachment of a dimethylallyl moiety to 4-hydroxyphenylpyruvate. Herein
Nick J P Wierckx et al.
Journal of bacteriology, 190(8), 2822-2830 (2007-11-13)
The unknown genetic basis for improved phenol production by a recombinant Pseudomonas putida S12 derivative bearing the tpl (tyrosine-phenol lyase) gene was investigated via comparative transcriptomics, nucleotide sequence analysis, and targeted gene disruption. We show upregulation of tyrosine biosynthetic genes
Tomasz Borowski et al.
Biochemistry, 43(38), 12331-12342 (2004-09-24)
Density functional calculations using the B3LYP functional has been used to study the reaction mechanism of 4-hydroxyphenylpyruvate dioxygenase. The first part of the catalytic reaction, dioxygen activation, is found to have the same mechanism as in alpha-ketoglutarate-dependent enzymes; the ternary
Panqing He et al.
Biochemistry, 49(9), 1998-2007 (2010-02-02)
Hydroxymandelate synthase (HMS) catalyzes the committed step in the formation of p-hydroxyphenylglycine, a recurrent substructure of polycyclic nonribosomal peptide antibiotics such as vancomycin. HMS has the same structural fold as and uses the same substrates as 4-hydroxyphenylpyruvate dioxygenase (HPPD) (4-hydroxyphenylpyruvate
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