3-(4-HYDROXYPHENYL)PYRUVIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H8O4
Molecular Weight	180.1574
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 3-(4-HYDROXYPHENYL)PYRUVIC ACID

Structure Search

SMILES

OC(=O)C(=O)CC1=CC=C(O)C=C1

InChI

InChIKey=KKADPXVIOXHVKN-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Approval Year

PubMed

Title	Date	PubMed
Altered bile acid metabolism in liver disease: concurrent occurrence of C-1 and C-6 hydroxylated bile acid metabolites and their preferential excretion into urine.	1990 Feb	2324645
A murine model for type III tyrosinemia: lack of immunologically detectable 4-hydroxyphenylpyruvic acid dioxygenase enzyme protein in a novel mouse strain with hypertyrosinemia.	1991 Apr	2014797
Biosynthesis of nucleotides, flavins, and deazaflavins in Methanobacterium thermoautotrophicum.	1991 May 25	2033055
The tyrosine degradation gene hppD is transcriptionally activated by HpdA and repressed by HpdR in Streptomyces coelicolor, while hpdA is negatively autoregulated and repressed by HpdR.	2007 Aug	17640269
Study on the kinetics of keto-enol tautomerism of p-hydroxyphenylpyruvic acid using capillary electrophoresis.	2007 Dec 21	18021791
Exploration of intraclonal adaptation mechanisms of Pseudomonas brassicacearum facing cadmium toxicity.	2007 Nov	17922765
Metabolic transcription analysis of engineered Escherichia coli strains that overproduce L-phenylalanine.	2007 Sep 19	17880710
The influence of ortho- and para-diphenoloxidase substrates on pigment formation in black yeast-like fungi.	2008	19287525
Detection of Plasmodium falciparum derived macrophage migration inhibitory factor homologue in the sera of malaria patients.	2008 Apr	18262164
Two roads diverged: the structure of hydroxymandelate synthase from Amycolatopsis orientalis in complex with 4-hydroxymandelate.	2008 Feb 19	18215022
Molecular cloning and characterization of Plasmodium falciparum transketolase.	2008 Jul	18456347
Experience of nitisinone for the pharmacological treatment of hereditary tyrosinaemia type 1.	2008 May	18422479
Identification of a novel 4-hydroxyphenylpyruvate dioxygenase from the soil metagenome.	2008 May 30	18381065
Isolation of herbicide-resistant 4-hydroxyphenylpyruvate dioxygenase from cultured Coptis japonica cells.	2008 Nov	18997404
Characterization of the atromentin biosynthesis genes and enzymes in the homobasidiomycete Tapinella panuoides.	2008 Nov	18805498
Alkaptonuria diagnosed in a 4-month-old baby girl: a case report.	2008 Nov 13	19014543
Investigating the initial steps in the biosynthesis of cyanobacterial sunscreen scytonemin.	2008 Nov 19	18954141
Clinical, biochemical, and genetic analysis of a Korean neonate with hereditary tyrosinemia type 1.	2009	19569981
Influence of growth regulators and sucrose concentrations on growth and rosmarinic acid production in calli and suspension cultures of Coleus blumei.	2009	19173121
Characterization of keto-enol tautomerism of p-hydroxyphenylpyruvic acid using CE with amperometric detection and spectrometric analysis.	2009 Dec	20066679
A novel mutation causing mild, atypical fumarylacetoacetase deficiency (Tyrosinemia type I): a case report.	2009 Dec 15	20003495
PhhR binds to target sequences at different distances with respect to RNA polymerase in order to activate transcription.	2009 Dec 4	19781550
Characterization of a deep-sea sediment metagenomic clone that produces water-soluble melanin in Escherichia coli.	2009 Jan-Feb	18648877
NovQ is a prenyltransferase capable of catalyzing the addition of a dimethylallyl group to both phenylpropanoids and flavonoids.	2009 Jul	19557032
A comparative genomics approach to understanding the biosynthesis of the sunscreen scytonemin in cyanobacteria.	2009 Jul 24	19630972
Aspergillusol A, an alpha-glucosidase inhibitor from the marine-derived fungus Aspergillus aculeatus.	2009 Nov	19824618
Role of Bacillus subtilis BacB in the synthesis of bacilysin.	2009 Nov 13	19776011
13C-metabolic flux ratio and novel carbon path analyses confirmed that Trichoderma reesei uses primarily the respirative pathway also on the preferred carbon source glucose.	2009 Oct 29	19874611
Prenyl transfer to aromatic substrates in the biosynthesis of aminocoumarins, meroterpenoids and phenazines: the ABBA prenyltransferase family.	2009 Oct-Nov	19559450
Methyl jasmonate dramatically enhances the accumulation of phenolic acids in Salvia miltiorrhiza hairy root cultures.	2009 Sep	19570133
Characterization and expression profiling of 4-hydroxyphenylpyruvate dioxygenase gene (Smhppd) from Salvia miltiorrhiza hairy root cultures.	2009 Sep	19011990
Identification and Partial Characterization of an L-Tyrosine Aminotransferase (TAT) from Arabidopsis thaliana.	2010	21188077
[Studies on the clinical manifestation and SLC25A13 gene mutation of Chinese patients with neonatal intrahepatic cholestasis caused by citrin deficiency].	2010 Apr	20376801
Production of 4-hydroxyphenyllactic acid by Lactobacillus sp. SK007 fermentation.	2010 Apr	20226379
Structure and mechanism of the magnesium-independent aromatic prenyltransferase CloQ from the clorobiocin biosynthetic pathway.	2010 Dec 10	20946900
Metabolic engineering of cofactor F420 production in Mycobacterium smegmatis.	2010 Dec 29	21209917
Comparative transcriptomics and proteomics of p-hydroxybenzoate producing Pseudomonas putida S12: novel responses and implications for strain improvement.	2010 Jun	20449741
Identification and characterization of the PhhR regulon in Pseudomonas putida.	2010 Jun	20050871
Finding new enzymes from bacterial physiology: a successful approach illustrated by the detection of novel oxidases in Marinomonas mediterranea.	2010 Mar 5	20411113
The rate-limiting catalytic steps of hydroxymandelate synthase from Amycolatopsis orientalis.	2010 Mar 9	20112984
A new group of aromatic prenyltransferases in fungi, catalyzing a 2,7-dihydroxynaphthalene 3-dimethylallyl-transferase reaction.	2010 May 28	20351110
Tyrosine aminotransferase: biochemical and structural properties and molecular dynamics simulations.	2010 Nov	21153519
The arthrobacter arilaitensis Re117 genome sequence reveals its genetic adaptation to the surface of cheese.	2010 Nov 24	21124797
The structure of Haemophilus influenzae prephenate dehydrogenase suggests unique features of bifunctional TyrA enzymes.	2010 Oct 1	20944228
Prephenate decarboxylases: a new prephenate-utilizing enzyme family that performs nonaromatizing decarboxylation en route to diverse secondary metabolites.	2010 Oct 26	20863139
Hereditary tyrosinemia type 1 metabolites impair DNA excision repair pathways.	2010 Oct 8	20828540
RNAi-mediated suppression of isoprene emission in poplar transiently impacts phenolic metabolism under high temperature and high light intensities: a transcriptomic and metabolomic analysis.	2010 Sep	20526857
Tyrosine-derived 4-hydroxyphenylpyruvate reacts with ketone test fields of 3 commercially available urine dipsticks.	2010 Sep	20487432
The genome of a pathogenic rhodococcus: cooptive virulence underpinned by key gene acquisitions.	2010 Sep 30	20941392
Interaction of macrophage migration inhibitory factor with ceruloplasmin: role of labile copper ions.	2015 Oct	26091949

Patents

Name

Type

Language

3-(4-HYDROXYPHENYL)PYRUVIC ACID

Common Name

English

NSC-100738

Code

English

PYRUVIC ACID, (P-HYDROXYPHENYL)-

Common Name

English

NSC-666757

Code

English

TESTACID

Common Name

English

HPPA

Common Name

English

BENZENEPROPANOIC ACID, 4-HYDROXY-.ALPHA.-OXO-

Common Name

English

4-HYDROXY-.ALPHA.-OXOBENZENEPROPANOIC ACID

Systematic Name

English

3-(P-HYDROXYPHENYL)-2-OXOPROPIONIC ACID

Common Name

English

3-(P-HYDROXYPHENYL)PYRUVIC ACID

Common Name

English

3-(4-HYDROXYPHENYL)-2-OXOPROPIONIC ACID

Systematic Name

English

4-HYDROXYPHENYLPYRUVATE

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID80166017