156-39-8

Basic information

• Product Name: 4-Hydroxyphenylpyruvic acid
• Synonyms: Pyruvic acid, (p-hydroxyphenyl)-;Testacid;4-HYDROXYPHENYLPYRUVIC ACID 99%;4-Hydrixyphenyruvic acid;4-hydroxy-a-oxo-benzenepropanoic acid;Hydroxyphenylpyruvic acid;3-(4-Hydroxyphenyl)pyruvate;2-Oxo-3-(4-hydroxyphenyl)propionic acid
• CAS NO: 156-39-8
• Molecular Formula: C₉H₈O₄
• Molecular Weight: 180.16
• EINECS: 205-852-9
• Product Categories: Miscellaneous;API intermediates
• Mol File: 156-39-8.mol
• Article Data: 23

Chemical Properties

• Melting Point: 219-220 °C (dec.)(lit.)
• Boiling Point: 272.96°C (rough estimate)
• Flash Point: 198.3 °C
• Appearance: off-white to tan/crystalline
• Density: 1.2933 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.4500 (estimate)
• Storage Temp.: 2-8°C
• Solubility: ethanol: soluble50mg/mL
• PKA: 2.50±0.54(Predicted)
• Water Solubility: slightly soluble
• Stability: Hygroscopic
• BRN: 2691632
• CAS DataBase Reference: 4-Hydroxyphenylpyruvic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxyphenylpyruvic acid(156-39-8)
• EPA Substance Registry System: 4-Hydroxyphenylpyruvic acid(156-39-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: UZ1000000
• Hazardous Substances Data: 156-39-8(Hazardous Substances Data)

Usage

Description

4-Hydroxyphenylpyruvic acid, also known as HPPA, is an oxo carboxylic acid derived from pyruvic acid, with one of the methyl hydrogens substituted by a 4-hydroxyphenyl group. It is a grey to orange-brown powder and can be determined in pork meat and Iberian ham samples using a sensitive method of multiple reaction monitoring (MRM) by mass spectrometry.

Uses

Used in Pharmaceutical Industry:
4-Hydroxyphenylpyruvic acid is used as a general organic reagent for the synthesis of latifolicinin A analogs, which serve as inhibitors of breast cancer. Its role in the development of these analogs contributes to the fight against breast cancer and potentially other types of cancer.
Used in Analytical Chemistry:
4-Hydroxyphenylpyruvic acid is used in the preparation of amperometric biosensors for β-triketone herbicides based on hydroxyphenylpyruvate. These biosensors are essential tools in the detection and analysis of herbicide residues in the environment, agriculture, and food safety applications.

Purification Methods

p-Hydroxyphenylpyruvic acid [156-39-8] M 180.2, m 220o(dec), pKEst ~2.3. Crystallise it three times from 0.1M HCl/EtOH (4:1, v/v) immediately before use [Rose & Powell Biochem J 87 541 1963], or from Et2O. The 3,4-dinitrophenylhydrazone has m 178o. [Beilstein 10 IV 3630.]

InChI:InChI=1/C5H5N3O3/c6-3-1-2-7-5(9)4(3)8(10)11/h1-2H,(H3,6,7,9)

Upstream product

• 80171-33-1 5-(p-hydroxybenzylidene)hydantoin 
• 60-18-4 L-tyrosine 
• 73-22-3 L-Tryptophan 
• 32089-82-0 2-benzoylamino-3-(4-hydroxy-phenyl)-acrylic acid 
• 23508-35-2 (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid 
• 57-13-6 urea 
• 123-08-0 4-hydroxy-benzaldehyde 
• 543-24-8 N-acetylglycine 
• 1161931-09-4 coelenterazine hydroperoxide 
• 461-72-3 2,4-imidazolidinedione 
• 63-91-2 L-phenylalanine 
• 328-42-7 Oxalacetic acid 
• 583-92-6 4-methylthio-2-oxobutanoic acid 
• 156-06-9 2-oxo-3-(phenyl)propionic acid 

Downstream Products

• 56632-94-1 (+/-)-Norcoclaurine-1-carboxylic acid 
• 86627-84-1 3-(4-hydroxy-phenyl)-2-phenylhydrazono-propionic acid 
• 501-94-0 p-hydroxyphenethyl alcohol 
• 6482-98-0 2-hydroxy-3-(4-hydroxyphenyl)propanoic acid 
• 154722-74-4 methyl 2-oxo-3-(4-hydroxyphenyl)propionate 
• 451-13-8 homogentisic acid 
• 958255-24-8 (2E)-3-(4-hydroxyphenyl)-2-[(oxan-2-yloxy)imino]propanoic acid 
• 664994-80-3 3-(4-Hydroxy-phenyl)-2-[(E)-tetrahydro-pyran-2-yloxyimino]-propionic acid 
• 7339-87-9 4-hydroxyphenylacetaldehyde 
• 74637-93-7 (Z)-2-[3-Benzyl-5-(4-hydroxy-phenyl)-pyrazin-2-ylamino]-3-(4-hydroxy-phenyl)-acrylic acid methyl ester 
• 55779-48-1 coelenterazine 
• 176031-32-6 4-(3-biphenylyl)-2-(4-hydroxybenzyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine 
• 1198427-20-1 3-hydroxy-4-(4-hydroxyphenyl)-5-pentylfuran-2(5H)-one 
• 89919-57-3 (R)-3-(4-hydroxyphenyl)lactic acid 

Related news

A nonsense mutation in the 4-Hydroxyphenylpyruvic acid (cas 156-39-8) dioxygenase gene (Hpd) causes skipping of the constitutive exon and hypertyrosinemia in mouse strain III09/30/2019

4-Hydroxyphenylpyruvic acid dioxygenase (HPD; EC 1.13.11.27) is an important enzyme in tyrosine catabolism in most organisms. Decreased activity of 4-hydroxyphenylpyruvic acid dioxygenase in the liver of mouse strain III is associated with tyrosinemia. We report a nucleotide substitution that ge...detailed

Mutations in the 4-Hydroxyphenylpyruvic acid (cas 156-39-8) Dioxygenase Gene Are Responsible for Tyrosinemia Type III and Hawkinsinuria09/29/2019

The enzyme 4-hydroxyphenylpyruvic acid dioxygenase (HPD) catalyzes the reaction of 4-hydroxyphenylpyruvic acid to homogentisic acid in the tyrosine catabolism pathway. A deficiency in the catalytic activity of HPD may lead to tyrosinemia type III, an autosomal recessive disorder characterized by...detailed

Cloning, identification and expression analysis of Triticum aestivum 4-Hydroxyphenylpyruvic acid (cas 156-39-8) dioxygenase gene09/28/2019

Tocopherols, the lipid-soluble antioxidants known collectively as vitamin E, are produced by photosynthetic organisms, which play important roles not only in human and animals but plants as well. 4-hydroxyphenylpyruvic acid dioxygenase is the first committed enzyme of this biosynthesis pathway. ...detailed

Relevant articles and documents

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Formation of Coelenteramine from 2-Peroxycoelenterazine in the Ca2+-Binding Photoprotein Aequorin

Aequorin consists of apoprotein (apoAequorin) and (S)-2-peroxycoelenterazine (CTZ-OOH) and is considered to be a transient-state complex of an enzyme (apoAequorin) and a substrate (coelenterazine and molecular oxygen) in the enzymatic reaction. The degradation process of CTZ-OOH in aequorin was characterized under various conditions of protein denaturation. By acid treatment, the major product from CTZ-OOH was coelenteramine (CTM), but not coelenteramide (CTMD), and no significant luminescence was observed. The counterparts of CTM from CTZ-OOH were identified as 4-hydroxyphenylpyruvic acid (4HPPA) and 4-hydroxyphenylacetic acid (4HPAA) by liquid chromatography/electrospray ionization–time-of-flight mass spectrometry (LC/ESI-TOF-MS). In the luminescence reaction of aequorin with Ca2+, similar amounts of 4HPPA and 4HPAA were detected, indicating that CTM is formed by two pathways from CTZ-OOH through dioxetanone anion and not by hydrolysis from CTMD.

Butenolide derivative as well as preparation method and application thereof

The invention discloses a butenolide compound as well as a preparation method and an application thereof. The butenolide derivative has the inhibitory activity of protein tyrosine phosphatase 1B (PTP1B), improves insulin resistance of HepG2 cells, generates a remarkable hypoglycemic effect and can be used for preparing a medicine for treating diabetes mellitus.

Efficient Synthesis of Phenylacetate and 2-Phenylethanol by Modular Cascade Biocatalysis

The green and sustainable synthesis of chemicals from renewable feedstocks by a biotransformation approach has gained increasing attention in recent years. In this work, we developed enzymatic cascades to efficiently convert l-phenylalanine into 2-phenylethanol (2-PE) and phenylacetic acid (PAA), l-tyrosine into tyrosol (p-hydroxyphenylethanol, p-HPE) and p-hydroxyphenylacetic acid (p-HPAA). The enzymatic cascade was cast into an aromatic aldehyde formation module, followed by an aldehyde reduction module, or aldehyde oxidation module, to achieve one-pot biotransformation by using recombinant Escherichia coli. Biotransformation of 50 mM l-Phe produced 6.76 g/L PAA with more than 99 % conversion and 5.95 g/L of 2-PE with 97 % conversion. The bioconversion efficiencies of p-HPAA and p-HPE from l-Tyr reached to 88 and 94 %, respectively. In addition, m-fluoro-phenylalanine was further employed as an unnatural aromatic amino acid substrate to obtain m-fluoro-phenylacetic acid; '96 % conversion was achieved. Our results thus demonstrated high-yielding and potential industrial synthesis of above aromatic compounds by one-pot cascade biocatalysis.