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MilliporeSigma

114286

4-Hydroxyphenylpyruvic acid

98%

Synonym(s):

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

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$150.00

5 G

$639.00

$150.00

Estimated to ship onDecember 01, 2025Details

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About This Item

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

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assay

98%

form

solid

mp

219-220 °C (dec.) (lit.)

solubility

ethanol: soluble 50 mg/mL

functional group

carboxylic acid
ketone

SMILES string

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

InChI

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

InChI key

KKADPXVIOXHVKN-UHFFFAOYSA-N

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1 of 4

This Item
145505328022134341
4-Hydroxyphenylpyruvic acid 98%

Sigma-Aldrich

114286

4-Hydroxyphenylpyruvic acid

α-Cyano-4-hydroxycinnamic acid 97%

Sigma-Aldrich

145505

α-Cyano-4-hydroxycinnamic acid

4-Methylhippuric acid 98%

Sigma-Aldrich

328022

4-Methylhippuric acid

4-Phenylphenol 97%

Sigma-Aldrich

134341

4-Phenylphenol

assay

98%

assay

97%

assay

98%

assay

97%

solubility

ethanol: soluble 50 mg/mL

solubility

methanol: soluble 50 mg/mL, clear to slightly hazy, light yellow to yellow

solubility

-

solubility

methanol: soluble 50 mg/mL, clear, colorless

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

mp

219-220 °C (dec.) (lit.)

mp

245-250 °C (lit.)

mp

163-165 °C (lit.)

mp

164-166 °C (lit.)

form

solid

form

powder

form

powder

form

-

functional group

carboxylic acid

functional group

carboxylic acid, nitrile

functional group

amide, carboxylic acid

functional group

phenyl

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[1].

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>

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_germany

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
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
Dingding Shao et al.
Acta tropica, 106(1), 9-15 (2008-02-12)
Macrophage migration inhibitory factor homologues have been identified from several genera of parasites, including Plasmodium, and have shown some functional similarities to the host molecule. It was hypothesized that MIF molecules can act as a regulator in host-parasite interaction in
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
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
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