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Sigma-Aldrich

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
Beilstein:
2691632
EC Number:
205-852-9
MDL number:
MFCD00002591
UNSPSC Code:
12352100
PubChem Substance ID:
24847164
NACRES:
NA.22

Assay

98%

form

solid

mp

219-220 °C (dec.) (lit.)

solubility

ethanol: soluble 50 mg/mL

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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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.

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

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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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
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
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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
Lu Huang et al.
Journal of chromatography. A, 1175(2), 283-288 (2007-11-21)
The kinetics of keto-enol tautomerism of p-hydroxyphenylpyruvic acid (pHPP) as a model of alpha-carbonyl compounds in aqueous solution at room temperature (25 degrees C) was first investigated by capillary electrophoresis with UV detection at 200 nm. The two tautomers could
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