3-oxoadipic acid

3-oxohexanedioic acid

CAS: 689-31-6 C6 H8 O5 MW: 160.12576000

Identification

Name3-oxoadipic acid
IUPAC3-oxohexanedioic acid
CAS Number689-31-6
FDA UNII1379JRA56F
Molecular FormulaC6 H8 O5
Molecular Weight160.12576000
Nikkaji NumberJ309.041H
Beilstein1775833

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 412.25 °C. @ 760.00 mm Hg (est)
Flash Point 423.00 °F. TCC ( 217.30 °C. ) (est)
logP (o/w) -0.688 (est)
Soluble in water, 1e+006 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryinformation only not used for fragrances or flavors
Recommendation for 3-oxoadipic acid usage levels up tonot for fragrance use.
Recommendation for 3-oxoadipic acid flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

not found in nature

Synonyms

3-keto- adipate 3-keto adipic acid b-keto adipic acid b-oxo adipic acid 3-oxo hexane dioic acid 3-oxo hexanedioic acid hexanedioic acid, 3-oxo- PubMed: Beta-ketoadipic acid and muconolactone production from a lignin-related aromatic compound through the protocatechuate 3,4-metabolic pathway PubMed: The beta-ketoadipate pathway and the biology of self-identity PubMed: A new mode of ring cleavage of 2,3-dihydroxybenzoic acid in Tecoma stans (L.). Partial purification and properties of 2,3-dihydroxybenzoate 2,3-oxygenase PubMed: Metabolic profiles of serum samples from ground glass opacity represent potential diagnostic biomarkers for lung cancer PubMed: Development of a Plasmid-Free Biosynthetic Pathway for Enhanced Muconic Acid Production in Pseudomonas chlororaphis HT66 PubMed: Degradation of 1,2,3,4-tetrachlorobenzene by pseudomonas chlororaphis RW71 PubMed: Competitive relationship between protocatechuic acid and p-aminosalicylic acid for a cellular transport mechanism PubMed: Biotechnological opportunities with the ?-ketoadipate pathway PubMed: Mechanism of aniline degradation by yeast strain Candida methanosorbosa BP-6 PubMed: The bacterial oxidation of aromatic compounds; III. The enzymatic oxidation of catechol and protocatechuic acid to beta-ketoadipic acid PubMed: 3-Hydroxydicarboxylic and 3-ketodicarboxylic aciduria in three patients: evidence for a new defect in fatty acid oxidation at the level of 3-ketoacyl-CoA thiolase PubMed: New Findings on Aromatic Compounds' Degradation and Their Metabolic Pathways, the Biosurfactant Production and Motility of the Halophilic Bacterium Halomonas sp. KHS3 PubMed: Modified 3-oxoadipate pathway for the biodegradation of methylaromatics in Pseudomonas reinekei MT1 PubMed: Stress responses of Acinetobacter strain Y during phenol degradation PubMed: Aerobic benzoyl-coenzyme A (CoA) catabolic pathway in Azoarcus evansii: conversion of ring cleavage product by 3,4-dehydroadipyl-CoA semialdehyde dehydrogenase PubMed: The old 3-oxoadipate pathway revisited: new insights in the catabolism of aromatics in the saprophytic fungus Aspergillus nidulans PubMed: Enzymatic degradation of beta-ketoadipic acid PubMed: The journey, not the arrival matters PubMed: Gentisate and 3-oxoadipate pathways in the yeast Candida parapsilosis: identification and functional analysis of the genes coding for 3-hydroxybenzoate 6-hydroxylase and 4-hydroxybenzoate 1-hydroxyla PubMed: Key enzymes of the protocatechuate branch of the beta-ketoadipate pathway for aromatic degradation in Corynebacterium glutamicum PubMed: The bacterial oxidation of phenol to beta-ketoadipic acid PubMed: Characterization of a new catechol branch of the beta-ketoadipate pathway induced for benzoate degradation in Acinetobacter lwoffii K24 PubMed: Some strains that have converged to infect Prunus spp. trees are members of distinct Pseudomonas syringae genomospecies and ecotypes as revealed by in silico genomic comparison PubMed: A two-component monooxygenase catalyzes both the hydroxylation of p-nitrophenol and the oxidative release of nitrite from 4-nitrocatechol in Bacillus sphaericus JS905 PubMed: Enzymology of the beta-ketoadipate pathway in Trichosporon cutaneum PubMed: The formation of beta-ketoadipic acid by bacterial fission of aromatic rings PubMed: Muconolactone isomerase of the 3-oxoadipate pathway catalyzes dechlorination of 5-chloro-substituted muconolactones PubMed: Comparative genomics of the protocatechuate branch of the ?-ketoadipate pathway in the Roseobacter lineage PubMed: beta-Ketoadipate pathway in Trichosporon cutaneum modified for methyl-substituted metabolites PubMed: Comparative genomics reveals genes significantly associated with woody hosts in the plant pathogen Pseudomonas syringae PubMed: Proteogenomic Characterization of Monocyclic Aromatic Hydrocarbon Degradation Pathways in the Aniline-Degrading Bacterium Burkholderia sp. K24 PubMed: Global proteome survey of protocatechuate- and glucose-grown Corynebacterium glutamicum reveals multiple physiological differences PubMed: Enhanced detection and characterization of protocatechuate 3,4-dioxygenase in Acinetobacter lwoffii K24 by proteomics using a column separation PubMed: Metabolic gene clusters encoding the enzymes of two branches of the 3-oxoadipate pathway in the pathogenic yeast Candida albicans PubMed: Characterization of the beta-ketoadipate pathway in Sinorhizobium meliloti PubMed: PseudoCyc, a pathway-genome database for Pseudomonas aeruginosa PubMed: The mechanism of formation of beta-ketoadipic acid by bacteria PubMed: Biodegradation of 8-anilino-1-naphthalenesulfonic acid by Pseudomonas aeruginosa PubMed: Crystallization and preliminary X-ray crystallographic analysis of gamma-carboxymucolactone decarboxylase from Sulfolobus solfataricus PubMed: Integration of chemotaxis, transport and catabolism in Pseudomonas putida and identification of the aromatic acid chemoreceptor PcaY PubMed: PcaO positively regulates pcaHG of the beta-ketoadipate pathway in Corynebacterium glutamicum PubMed: Influence of allosteric regulators on individual steps in the reaction catalyzed by Mycobacterium tuberculosis 2-hydroxy-3-oxoadipate synthase PubMed: The lin genes for ?-hexachlorocyclohexane degradation in Sphingomonas sp. MM-1 proved to be dispersed across multiple plasmids PubMed: Genomic organization and genomic structural rearrangements of Sphingobium japonicum UT26, an archetypal ?-hexachlorocyclohexane-degrading bacterium PubMed: In vitro reconstitution of the catabolic reactions catalyzed by PcaHG, PcaB, and PcaL: the protocatechuate branch of the ?-ketoadipate pathway in Rhodococcus jostii RHA1 PubMed: p-Chloromercuribenzoate specifically modifies thiols associated with the active sites of beta-ketoadipate enol-lactone hydrolase and succinyl CoA: beta-ketoadipate CoA transferase PubMed: Novel nuclear magnetic resonance spectroscopy methods demonstrate preferential carbon source utilization by Acinetobacter calcoaceticus PubMed: The crystal structure of maleylacetate reductase from Rhizobium sp. strain MTP-10005 provides insights into the reaction mechanism of enzymes in its original family PubMed: Elucidation of the 4-hydroxyacetophenone catabolic pathway in Pseudomonas fluorescens ACB PubMed: Genome-wide investigation and functional characterization of the beta-ketoadipate pathway in the nitrogen-fixing and root-associated bacterium Pseudomonas stutzeri A1501 PubMed: Characterization of beta-ketoadipate pathway from multi-drug resistance bacterium, Acinetobacter baumannii DU202 by proteomic approach PubMed: Cytochrome P450rm from Rhodotorula minuta catalyzes 4-hydroxylation of benzoate PubMed: Biological chlorination. III. beta-Ketoadipate chlorinase: a soluble enzyme system PubMed: Degradation of aromatic compounds through the ?-ketoadipate pathway is required for pathogenicity of the tomato wilt pathogen Fusarium oxysporum f. sp. lycopersici PubMed: Analysis of ten Brucella genomes reveals evidence for horizontal gene transfer despite a preferred intracellular lifestyle PubMed: The beta-ketoadipate pathway of Acinetobacter baylyi undergoes carbon catabolite repression, cross-regulation and vertical regulation, and is affected by Crc PubMed: From xenobiotic to antibiotic, formation of protoanemonin from 4-chlorocatechol by enzymes of the 3-oxoadipate pathway PubMed: Purification and characterization of 4-methylmuconolactone methylisomerase, a novel enzyme of the modified 3-oxoadipate pathway in the gram-negative bacterium Alcaligenes eutrophus JMP 134 PubMed: Genomic analysis of polycyclic aromatic hydrocarbon degradation in Mycobacterium vanbaalenii PYR-1 PubMed: Differences between collagen hydroxylases and 2-oxoglutarate dehydrogenase in their inhibition by structural analogues of 2-oxoglutarate PubMed: Diverse organization of genes of the beta-ketoadipate pathway in members of the marine Roseobacter lineage PubMed: Key aromatic-ring-cleaving enzyme, protocatechuate 3,4-dioxygenase, in the ecologically important marine Roseobacter lineage PubMed: Differential DNA bending introduced by the Pseudomonas putida LysR-type regulator, CatR, at the plasmid-borne pheBA and chromosomal catBC promoters PubMed: Regulation of the pcaIJ genes for aromatic acid degradation in Pseudomonas putida PubMed: Genomic analysis of the aromatic catabolic pathways from Pseudomonas putida KT2440 PubMed: Characterization of the genes encoding beta-ketoadipate: succinyl-coenzyme A transferase in Pseudomonas putida PubMed: The fluorene catabolic linear plasmid in Terrabacter sp. strain DBF63 carries the beta-ketoadipate pathway genes, pcaRHGBDCFIJ, also found in proteobacteria PubMed: Benzoate degradation via the ortho pathway in Alcaligenes eutrophus is perturbed by succinate PubMed: Biodegradation of diphenyl ether and its monohalogenated derivatives by Sphingomonas sp. strain SS3 PubMed: Origins of metabolic diversity: substitution of homologous sequences into genes for enzymes with different catalytic activities PubMed: The modified beta-ketoadipate pathway in Rhodococcus rhodochrous N75: enzymology of 3-methylmuconolactone metabolism PubMed: PcaR-mediated activation and repression of pca genes from Pseudomonas putida are propagated by its binding to both the -35 and the -10 promoter elements PubMed: Transcriptional cross-regulation of the catechol and protocatechuate branches of the beta-ketoadipate pathway contributes to carbon source-dependent expression of the Acinetobacter sp. strain ADP1 po PubMed: Repression of 4-hydroxybenzoate transport and degradation by benzoate: a new layer of regulatory control in the Pseudomonas putida beta-ketoadipate pathway PubMed: Characterization of a second tfd gene cluster for chlorophenol and chlorocatechol metabolism on plasmid pJP4 in Ralstonia eutropha JMP134(pJP4) PubMed: A putative porin gene of Burkholderia sp. NK8 involved in chemotaxis toward ?-ketoadipate PubMed: MECHANISM OF BETA-KETOADIPATE FORMATION BY BACTERIA PubMed: Maleylacetate reductase of Pseudomonas sp. strain B13: dechlorination of chloromaleylacetates, metabolites in the degradation of chloroaromatic compounds PubMed: Structure-activity relationships delineate how the maize pathogen Cochliobolus heterostrophus uses aromatic compounds as signals and metabolites PubMed: Metabolism of aromatic compounds by Caulobacter crescentus PubMed: Metabolism of resorcinol and salicylate in Aspergillus niger PubMed: Enzymes of the beta-ketoadipate pathway in Pseudomonas putida: primary and secondary kinetic and equilibrium deuterium isotope effects upon the interconversion of (+)-muconolactone to cis,cis-muconat PubMed: Supraoperonic clustering of pca genes for catabolism of the phenolic compound protocatechuate in Agrobacterium tumefaciens PubMed: Acetate utilization is inhibited by benzoate in Alcaligenes eutrophus: evidence for transcriptional control of the expression of acoE coding for acetyl coenzyme A synthetase PubMed: Regulation of phenolic catabolism in Rhizobium leguminosarum biovar trifolii PubMed: Enzymes of the beta-ketoadipate pathway are inducible in Rhizobium and Agrobacterium spp. and constitutive in Bradyrhizobium spp PubMed: Unusual G + C content and codon usage in catIJF, a segment of the ben-cat supra-operonic cluster in the Acinetobacter calcoaceticus chromosome PubMed: Cloning of catBCIJFD genes for catechol degradation into chromosomal pobA and genetic stability of the recombinant Acinetobacter calcoaceticus PubMed: Degradation of phenolic compounds by the yeast Candida tropicalis HP 15. I. Physiology of growth and substrate utilization PubMed: Biological distribution and physiological role of the beta-ketoadipate transport system PubMed: Enzymes of the beta-ketoadipate pathway in Pseudomonas putida: kinetic and magnetic resonance studies of the cis,cis-muconate cycloisomerase catalyzed reaction PubMed: [Acinetobacter calcoaceticus strain with a wide spectrum of utilizing aromatic compounds and carrying a plasmid for resorcin degradation] PubMed: Participation of the beta-ketoadipate transport system in chemotaxis PubMed: pWW174: a large plasmid from Acinetobacter calcoaceticus encoding benzene catabolism by the beta-ketoadipate pathway