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3-oxoadipic acid
3-oxohexanedioic acid

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Name:3-oxohexanedioic acid
CAS Number: 689-31-6Picture of molecule3D/inchi
FDA UNII: 1379JRA56F
Nikkaji Web:J309.041H
Beilstein Number:1775833
XlogP3-AA:-0.90 (est)
Molecular Weight:160.12576000
Formula:C6 H8 O5
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:information only not used for fragrances or flavors
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
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)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
3-Oxoadipic acid 95%
Sigma-Aldrich: Aldrich
For experimental / research use only.
3-oxoAdipic Acid 98%
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
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.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :93
National Institute of Allergy and Infectious Diseases:Data
3-oxohexanedioic acid
Chemidplus:0000689316
 
References:
 3-oxohexanedioic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):93
Pubchem (sid):134976045
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
UM BBD:Search
KEGG (GenomeNet):C00846
HMDB (The Human Metabolome Database):HMDB00398
FooDB:FDB022015
Export Tariff Code:2918.30.5000
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
3-keto-adipate
3-ketoadipic acid
b-ketoadipic acid
b-oxoadipic acid
3-oxohexane dioic acid
3-oxohexanedioic acid
 hexanedioic acid, 3-oxo-
 

Articles:

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
 
Notes:
3-Oxoadipic acid is a regularly occurring Adipic dicarboxylic acid human metabolite found occasionally in biofluids of healthy individuals. (PMIDs 8340451, 1769109, 2338430) Increased amounts of 3-Oxoadipic acid are excreted after ingestion of Sebacic acid, supporting the hypothesis that dicarboxylic acids are degraded by ordinary beta-oxidation. (PMID 3220884) [HMDB]
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