114-76-1 Usage
Uses
Different sources of media describe the Uses of 114-76-1 differently. You can refer to the following data:
1. Sodium phenylpyruvate is a substrate for phenylpyruvate decarboxylase and phenylpyruvate tautomerase.It inhibits amino acid formation and depresses oxygen consumption.
2. Phenylpyruvic acid, sodium salt is a substrate for phenylpyruvate decarboxylase and phenylpyruvate tautomerase.
Biological Activity
Sodium phenylpyruvate (Phenylpyruvic acid sodium salt) inhibits amino acid formation and depresses oxygen consumption.
Enzyme inhibitor
This aromatic a-keto acid and PKU biomarker (FWfree-acid = 164.16 g/mol; CAS 156-06-9 for acid; CAS 114-76-1 for sodium salt; CAS 51828-93-4 for calcium salt); lmax = 320 nm, e = 17500 M–1 cm–1 in 0.7 M NaOH), also known as 2-oxo-3-phenylpropanoic acid and a-oxohydrocinnamic acid, is readily formed by the action of a number of aminotransferases on phenylalanine. Phenylpyruvate is only slightly soluble in boiling water but is soluble in ethanol and diethyl ether. The solid oxidizes in air and decomposes on storage, if not dry. Sodium phenylpyruvate is a watersoluble monohydrate salt. Phenylketonuria: Phenylpyruvate is present at high urinary concentrations in phenylalanine monooxygenase deficiency, better known as Phenylketonuria. Indeed, individuals suffering PKU tend to excrete urine containing large quantities of phenyl-pyruvate, phenyl-acetate and phenyl-lactate, along with phenylalanine. If untreated, mental retardation and microcephaly are evident by the first year, along with irritability, epileptic seizures, and skin lesions. Target(s): acetolactate synthase; aldehyde reductase; apyrase; branched-chain a-keto acid dehydrogenase; [branched-chain a-keto-acid dehydrogenase] kinase, or [3-methyl-2-oxobutanoate dehydrogenase (acetyl-transferring)] kinase; carnitine-acylcarnitine translocase; cathepsin D; choline acetyltransferase; 3-deoxy-7-phosphoheptulonate synthase, or 3-deoxy-D-arabino-heptulosonate 7-phosphate synthetase; dihydropteridine reductase; diphosphomevalonate decarboxylase; glutamate decarboxylase; glutamine:pyruvate aminotransferase; glycerate dehydrogenase, weakly inhibited; hexokinase (human brain), Ki = 2 mM; histidine decarboxylase; 4- hydroxyphenylpyruvate dioxygenase; 3a-hydroxysteroid dihydrogenase; 3b-hydroxysteroid dehydrogenase; hypothalamus acid proteinase; indolepyruvate decarboxylase, Ki = 50 μM; kynureninase; L-lactate dehydrogenase; L-lactate dehydrogenase (cytochrome); mercaptopyruvate sulfurtransferase; mevalonate-5-pyrophosphate decarboxylase; oxaloacetate tautomerase; phenylalanine ammonia-lyase; phenylalanyltRNA synthetase, weakly inhibited, Ki = 7.6 mM; pyruvate carboxylase; pyruvate decarboxylase; pyruvate dehydrogenase; pyruvate kinase (human), Ki = 8.5 mM; pyruvate oxidase; pyruvate transport; stearoyl-CoA 9-desaturase; tryptophan 2- monooxygenase; tryptophan 5-monooxygenase; tyrosinase; and tyrosine 2,3-aminomutase.
Purification Methods
The salt should have no OH broad bands in the IR at ~3000cm-1. If these are present, then they are due either to water contamination or to the presence of free acid. For the first case dry the solid thoroughly in a vacuum over P2O5, and in the latter case wash the salt well with Et2O in vacuo till free of acid. Alternatively add a slight excess of the free acid (cf p 332) in EtOH to ethanolic NaOH, evaporate to dryness and extract excess acid from the salt with dry Et2O. [Beilstein 10 I 325.]
Check Digit Verification of cas no
The CAS Registry Mumber 114-76-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 4 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 114-76:
(5*1)+(4*1)+(3*4)+(2*7)+(1*6)=41
41 % 10 = 1
So 114-76-1 is a valid CAS Registry Number.
InChI:InChI=1/C9H8O3.Na.H2O/c10-8(9(11)12)6-7-4-2-1-3-5-7;;/h1-5H,6H2,(H,11,12);;1H2/q;+1;/p-1
114-76-1Relevant articles and documents
Mechanism of the Hydrolysis of (Z)-4-Benzylidene-2-methyloxazolin-5-one or (Z)-4-Benzylidene-2-phenyloxazolin-5-one Derivatives
Suh, Junghun,Lee, Eun,Myoung, Young Chan,Kim, Minwoo,Kim, Soodan
, p. 977 - 980 (1985)
The methyl (1a) and the phenyl (2) derivatives of (Z)-4-benzylideneoxazolin-5-one were hydrolyzed at comparable rates under alkaline conditions.In contrast, the acidic hydrolysis of 2 was at least 10E5 times slower than that of 1a.The Hammett ρ value obtained from the acidic hydrolysis of the phenyl substituted derivatives of 1a was 0.20 +/- 0.09 while that from the corresponding basic hydrolysis was 1.50 +/- 0.11.Methanolysis of 1a under basic conditions produced the methyl ester of (Z)-α-(acetylamino)cinnamic acid, and that under acidic conditions led to products consistent with the attack of methanol at the imine carbon.These results indicate that the alkaline hydrolysis of the oxazolin-5-one derivatives occurs through nucleophilic attack at the carbonyl carbon of the substrate and the acidic hydrolysis through that at the imine carbon.
Synthesis of isotopically labelled L-phenylalanine and L-tyrosine
Raap, Jan,Nieuwenhuis, Saskia,Creemers, Alain,Hexspoor, Sander,Kragl, Udo,Lugtenburg, Johan
, p. 2609 - 2621 (2007/10/03)
A synthetic route to stable-isotope-substituted L-phenylalanine is presented, which allows the introduction of 13C, 15N, and deuterium labels at any position or combination of positions. For labelling of the aromatic ring, a synthetic route to ethyl benzoate (or benzonitrile) has been developed, based on the electrocyclic ring-closure of a 1,6-disubstituted hexatriene system, with in situ aromatization by elimination of one (amino) substituent. Several important (highly isotopically enriched) synthons have been prepared, namely benzonitrile, benzaldehyde, ethyl benzoate, and ethyl diphenyloxyacetate. Labelled L-phenylalanines have been synthesized from both aromatic precursors by initial conversion into sodium phenylpyruvate and subsequent transformation of this intermediate into the L-α-amino acid by an enzymatic reductive amination reaction. In this manner, highly enriched phenylalanines are obtained on the 10-gram scale and with high enantiomeric purities (≥ 99% ee). The method has been validated by the synthesis of [1'13C]-L-Phe and [2-D]-L-Phe. In addition, two methods are described for the introduction of isotopes into L-tyrosine starting from the isotopically enriched precursors benzonitrile and ethyl benzoate.
Dioxolanones as Synthetic Intermediates. Part 1. Synthesis of α-Keto Acids, α-Keto Aldehydes, and α-Ketols
Ramage, Robert,Griffiths, Gareth J.,Shutt, Fiona E.,Sweeney, John N. A.
, p. 1531 - 1537 (2007/10/02)
2,2-Pentamethylene-1,3-dioxolan-4-one (10) has been elaborated to provide 5'-ylidene derivatives using a Wittig approach.This apparently novel class of compounds is subject to nucleophilic attack at the 4-position because of strain inherent in the 5-membered ring.Thus alkaline hydrolysis leads to the formation of α-keto acids; hydride reduction of dioxolanones incorporating conjugated aryl substituents using di-isobutylaluminium hydride leads to α-keto-aldehydes; the reaction of dioxolanone (15) with methylmagnesium iodide gave the α-ketol (40).