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1460-34-0,MFCD00002582
Catalog No.:AA003JMJ

1460-34-0 | 3-Methyl-2-oxovaleric acid

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250mg
≥95.0%
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$163.00   $114.00
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1g
>95.0%(GC)(T)
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$240.00   $168.00
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5g
>95.0%(GC)(T)
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA003JMJ
Chemical Name:
3-Methyl-2-oxovaleric acid
CAS Number:
1460-34-0
Molecular Formula:
C6H10O3
Molecular Weight:
130.1418
MDL Number:
MFCD00002582
SMILES:
CC(C(=O)C(=O)O)CC
FEMA Number:
3870
Properties
Properties
 
BP:
190.5°C at 760 mmHg  
Form:
Solid  
MP:
42°C  
Storage:
2-8℃;  

Computed Properties
 
Complexity:
128  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
9  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
3  
Undefined Atom Stereocenter Count:
1  
XLogP3:
1.1  

Downstream Synthesis Route

[1]LiebigsAnnalenderChemie,1988,p.485-486

[1]TetrahedronLetters,1995,vol.36,p.5179-5182

[2]ChemCatChem,2013,vol.5,p.3538-3542

[3]OrganicLetters,2019,vol.21,p.709-713

[1]JournaloftheAmericanChemicalSociety,2004,vol.126,p.3020-3021

[1]Vedha-Peters,Kavitha;Gunawardana,Manjula;Rozzell,J.David;Novick,ScottJ.[JournaloftheAmericanChemicalSociety,2006,vol.128,#33,p.10923-10929]

[1]Rodriguez,GabrielM;Tashiro,Yohei;Atsumi,Shota[NatureChemicalBiology,2014,vol.10,#4,p.259-265]

Literature

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Journal: Food microbiology 20120401

Title: Virtual screening and evaluation of Ketol-Acid Reducto-Isomerase (KARI) as a putative drug target for Aspergillosis.

Journal: Clinical proteomics 20120101

Title: Recent progress in synthetic biology for microbial production of C3-C10 alcohols.

Journal: Frontiers in microbiology 20120101

Title: Identification and characterization of the pyridomycin biosynthetic gene cluster of Streptomyces pyridomyceticus NRRL B-2517.

Journal: The Journal of biological chemistry 20110610

Title: Metabonomic investigation of single and multiple strain Trypanosoma brucei brucei infections.

Journal: The American journal of tropical medicine and hygiene 20110105

Title: From amino acid to glucosinolate biosynthesis: protein sequence changes in the evolution of methylthioalkylmalate synthase in Arabidopsis.

Journal: The Plant cell 20110101

Title: The development of metabolomic sampling procedures for Pichia pastoris, and baseline metabolome data.

Journal: PloS one 20110101

Title: Comparative analyses imply that the enigmatic Sigma factor 54 is a central controller of the bacterial exterior.

Journal: BMC genomics 20110101

Title: Chemometric analysis of biofluids from mice experimentally infected with Schistosoma mansoni.

Journal: Parasites & vectors 20110101

Title: Metabolic changes reveal the development of schistosomiasis in mice.

Journal: PLoS neglected tropical diseases 20100801

Title: Engineering Corynebacterium glutamicum for isobutanol production.

Journal: Applied microbiology and biotechnology 20100701

Title: Characterization of the branched-chain amino acid aminotransferase enzyme family in tomato.

Journal: Plant physiology 20100701

Title: Integration of metabolomics and transcriptomics data to aid biomarker discovery in type 2 diabetes.

Journal: Molecular bioSystems 20100501

Title: The effects of branched-chain amino acid interactions on growth performance, blood metabolites, enzyme kinetics and transcriptomics in weaned pigs.

Journal: The British journal of nutrition 20100401

Title: Genome sequence of the pea aphid Acyrthosiphon pisum.

Journal: PLoS biology 20100201

Title: Pentanol isomer synthesis in engineered microorganisms.

Journal: Applied microbiology and biotechnology 20100101

Title: Prediction of novel synthetic pathways for the production of desired chemicals.

Journal: BMC systems biology 20100101

Title: Compartmentalization of the Edinburgh Human Metabolic Network.

Journal: BMC bioinformatics 20100101

Title: The chemistry, pharmacologic, and therapeutic applications of Polyalthia longifolia.

Journal: Pharmacognosy reviews 20100101

Title: Arabidopsis thaliana encodes a bacterial-type heterodimeric isopropylmalate isomerase involved in both Leu biosynthesis and the Met chain elongation pathway of glucosinolate formation.

Journal: Plant molecular biology 20091001

Title: The role of free amino acids in semen of rainbow trout Oncorhynchus mykiss and carp Cyprinus carpio.

Journal: Journal of fish biology 20090901

Title: Streptococcus pneumoniae and Staphylococcus aureus pneumonia induce distinct metabolic responses.

Journal: Journal of proteome research 20090601

Title: Metabolite profiling of human amniotic fluid by hyphenated nuclear magnetic resonance spectroscopy.

Journal: Analytical chemistry 20080801

Title: NMR-spectroscopy-based metabonomic approach to the analysis of Bay41-4109, a novel anti-HBV compound, induced hepatotoxicity in rats.

Journal: Toxicology letters 20070928

Title: Effect of the branched-chain alpha-keto acids accumulating in maple syrup urine disease on S100B release from glial cells.

Journal: Journal of the neurological sciences 20070915

Title: Synaptic plasma membrane Na(+), K (+)-ATPase activity is significantly reduced by the alpha-keto acids accumulating in maple syrup urine disease in rat cerebral cortex.

Journal: Metabolic brain disease 20070301

Title: Branched chain keto-acids exert biphasic effects on alpha-ketoglutarate-stimulated respiration in intact rat liver mitochondria.

Journal: Neurochemical research 20070101

Title: Bioactive diterpenes from the fruits of Detarium microcarpum.

Journal: Journal of natural products 20060501

Title: Hypobaric hypoxia affects endogenous levels of alpha-keto acids in murine heart ventricles.

Journal: Biochemical and biophysical research communications 20060414

Title: Creatine and antioxidant treatment prevent the inhibition of creatine kinase activity and the morphological alterations of C6 glioma cells induced by the branched-chain alpha-keto acids accumulating in maple syrup urine disease.

Journal: Cellular and molecular neurobiology 20060201

Title: Branched-chain alpha-keto acids accumulating in maple syrup urine disease induce reorganization of phosphorylated GFAP in C6-glioma cells.

Journal: Metabolic brain disease 20050901

Title: alpha-keto acids accumulating in maple syrup urine disease stimulate lipid peroxidation and reduce antioxidant defences in cerebral cortex from young rats.

Journal: Metabolic brain disease 20050601

Title: Protective effect of alpha-keto-beta-methyl-n-valeric acid on BV-2 microglia under hypoxia or oxidative stress.

Journal: Annals of the New York Academy of Sciences 20050501

Title: Branched-chain fatty acid biosynthesis in a branched-chain amino acid aminotransferase mutant of Staphylococcus carnosus.

Journal: FEMS microbiology letters 20050201

Title: Modeling Lactococcus lactis using a genome-scale flux model.

Journal: BMC microbiology 20050101

Title: alpha-keto-beta-methyl-n-valeric acid diminishes reactive oxygen species and alters endoplasmic reticulum Ca(2+) stores.

Journal: Free radical biology & medicine 20041201

Title: Evidence that the branched-chain alpha-keto acids accumulating in maple syrup urine disease induce morphological alterations and death in cultured astrocytes from rat cerebral cortex.

Journal: Glia 20041115

Title: Mitochondrial enzymes and endoplasmic reticulum calcium stores as targets of oxidative stress in neurodegenerative diseases.

Journal: Journal of bioenergetics and biomembranes 20040801

Title: alpha-Aminoadipate aminotransferase from an extremely thermophilic bacterium, Thermus thermophilus.

Journal: Microbiology (Reading, England) 20040701

Title: A conditional marker gene allowing both positive and negative selection in plants.

Journal: Nature biotechnology 20040401

Title: Alpha-keto-beta-methylvaleric acid increases the in vitro phosphorylation of intermediate filaments in cerebral cortex of young rats through the gabaergic system.

Journal: Journal of the neurological sciences 20040115

Title: Intrahippocampal administration of the alpha-keto acids accumulating in maple syrup urine disease provokes learning deficits in rats.

Journal: Pharmacology, biochemistry, and behavior 20040101

Title: Catabolism of leucine to branched-chain fatty acids in Staphylococcus xylosus.

Journal: Journal of applied microbiology 20040101

Title: Inhibition of brain energy metabolism by the alpha-keto acids accumulating in maple syrup urine disease.

Journal: Biochimica et biophysica acta 20031120

Title: Inhibition of alpha-ketoglutarate dehydrogenase complex promotes cytochrome c release from mitochondria, caspase-3 activation, and necrotic cell death.

Journal: Journal of neuroscience research 20031015

Title: Biosynthesis of branched-chain fatty acid in bacilli: FabD (malonyl-CoA:ACP transacylase) is not essential for in vitro biosynthesis of branched-chain fatty acids.

Journal: Bioscience, biotechnology, and biochemistry 20031001

Title: Substrate specificity and kinetic isotope effect analysis of the Eschericia coli ketopantoate reductase.

Journal: Biochemistry 20030930

Title: Lacticin 3147 favours isoleucine transamination by Lactococcus lactis IFPL359 in a cheese-model system.

Journal: Biotechnology letters 20030401

Title: Inhibition of the alpha-ketoglutarate dehydrogenase complex alters mitochondrial function and cellular calcium regulation.

Journal: Biochimica et biophysica acta 20030120

Title: Mycobacterium tuberculosis ketopantoate hydroxymethyltransferase: tetrahydrofolate-independent hydroxymethyltransferase and enolization reactions with alpha-keto acids.

Journal: Biochemistry 20030114

Title: Effect of the branched-chain alpha-ketoacids accumulating in maple syrup urine disease on the high molecular weight neurofilament subunit (NF-H) in rat cerebral cortex.

Journal: Metabolic brain disease 20020601

Title: Pharmacological evidence that alpha-ketoisovaleric acid induces convulsions through GABAergic and glutamatergic mechanisms in rats.

Journal: Brain research 20010309

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