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

Chemical Properties

grey to orange-brown powder

Uses

4-Hydroxyphenylpyruvic Acid is general organic reagent used in the synthesis of latifolicinin A analogs as inhibitors of breast cancer. Also used in the preparation of amperometric biosensors for β-triketone herbicides based on hydroxyphenylpyruvate.

Definition

ChEBI: An oxo carboxylic acid that is pyruvic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group.

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.

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 
• 52507-18-3 4-acetoxy-α-acetylamino-cinnamic acid 
• 32089-82-0 2-benzoylamino-3-(4-hydroxy-phenyl)-acrylic acid 
• 495-69-2 Hippuric Acid 
• 123-08-0 4-hydroxy-benzaldehyde 
• 60-18-4 L-tyrosine 
• 73-22-3 L-Tryptophan 
• 123955-02-2 potassium lespedezate 
• 23508-35-2 (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid 
• 57-13-6 urea 
• 80171-33-1 5-(4-hydroxybenzylidene)imidazolidine-2,4-dione 
• 80171-33-1 5-(4'-hydroxybenzylidene)-hydantoin 
• 556-02-5 tyrosine 
• 328-50-7 α-ketoglutaric acid 

Downstream Products

• 104443-43-8 urdamycin C 
• 82112-32-1 C₂₁H₃₆O₄Si₂ 
• 64710-34-5 1-carboxy-6,7-dihydroxy-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride 
• 99208-27-2 3-(4-Hydroxy-benzyl)-6,7-dimethoxy-1H-quinoxalin-2-one 
• 132063-81-1 (Z)-2-(2-Benzyl-8,10-bis-benzyloxy-5,6-dihydro-benzo[f]quinoxalin-3-ylamino)-3-(4-hydroxy-phenyl)-acrylic acid 
• 60-18-4 L-tyrosine 
• 74637-92-6 (Z)-2-[3-Benzyl-5-(4-hydroxy-phenyl)-pyrazin-2-ylamino]-3-(4-hydroxy-phenyl)-acrylic acid 
• 55779-48-1 coelenterazine 
• 862252-61-7 methyl (4-hydroxyphenyl)pyruvate, enol form 
• 7339-87-9 4-hydroxyphenylacetaldehyde 
• 1082955-11-0 C₁₉H₁₉NO₅ 
• 1082955-10-9 C₁₉H₁₉NO₅ 
• 1082955-09-6 C₁₈H₁₇NO₃ 
• 1006373-58-5 soraphinol A 

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.

Biocascade Synthesis of L-Tyrosine Derivatives by Coupling a Thermophilic Tyrosine Phenol-Lyase and L-Lactate Oxidase

A one-pot biocascade of two enzymatic steps catalyzed by an l-lactate oxidase and a tyrosine phenol-lyase has been successfully developed in the present study. The reaction provides an efficient method for the synthesis of l-tyrosine derivatives, which exhibits readily available starting materials and excellent yields. In the first step, an in situ generation of pyruvate from readily available bio-based l-lactate catalyzed by a highly active l-lactate oxidase from Aerococcus viridans (AvLOX) was developed (using oxygen as oxidant and catalase as hydrogen peroxide removing reagent). Pyruvate thus produced underwent C–C coupling with phenol derivatives as acceptor substrate using specially designed thermophilic tyrosine phenol-lyase mutants from Symbiobacterium toebii (TTPL). Overall, this cascade avoids the high cost and easy decomposition of pyruvate and offered an efficient and environmentally friendly procedure for l-tyrosine derivatives synthesis.