3-oxoadipic acid
3-oxohexanedioic acid
Identification
| Name | 3-oxoadipic acid |
| IUPAC | 3-oxohexanedioic acid |
| CAS Number | 689-31-6 |
| FDA UNII | 1379JRA56F |
| Molecular Formula | C6 H8 O5 |
| Molecular Weight | 160.12576000 |
| Nikkaji Number | J309.041H |
| Beilstein | 1775833 |
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 SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | information only not used for fragrances or flavors |
| Recommendation for 3-oxoadipic acid usage levels up to | not for fragrance use. |
| Recommendation for 3-oxoadipic acid flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
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