498-21-5,MFCD00002659
Catalog No.:AA003279

498-21-5 | Methylsuccinic acid

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5g
95%
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$8.00   $6.00
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10g
95%
in stock  
$10.00   $7.00
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25g
95%
in stock  
$22.00   $16.00
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100g
95%
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$66.00   $46.00
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  • Technical Information
  • Properties
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA003279
Chemical Name:
Methylsuccinic acid
CAS Number:
498-21-5
Molecular Formula:
C5H8O4
Molecular Weight:
132.1146
MDL Number:
MFCD00002659
SMILES:
OC(=O)CC(C(=O)O)C
NSC Number:
5276
Properties
Properties
 
BP:
236.5 °C at 760 mmHg  
Form:
Solid  
MP:
110-115 °C  
Refractive Index:
1.4240 (estimate)  
Storage:
Keep in dry area;Room Temperature;  

Computed Properties
 
Complexity:
129  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
9  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0  
Rotatable Bond Count:
3  
Undefined Atom Stereocenter Count:
1  
Undefined Bond Stereocenter Count:
0  
XLogP3:
-0.2  

Literature

Title: Urinary Time- or Dose-Dependent Metabolic Biomarkers of Aristolochic Acid-Induced Nephrotoxicity in Rats.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20170301

Title: Cannabinoid receptor antagonist-induced striated muscle toxicity and ethylmalonic-adipic aciduria in beagle dogs.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20121001

Title: Biochemical, molecular, and clinical characteristics of children with short chain acyl-CoA dehydrogenase deficiency detected by newborn screening in California.

Journal: Molecular genetics and metabolism 20120501

Title: A temporal-omic study of Propionibacterium freudenreichii CIRM-BIA1 adaptation strategies in conditions mimicking cheese ripening in the cold.

Journal: PloS one 20120101

Title: M19 modulates skeletal muscle differentiation and insulin secretion in pancreatic β-cells through modulation of respiratory chain activity.

Journal: PloS one 20120101

Title: Dopamine induced neurodegeneration in a PINK1 model of Parkinson's disease.

Journal: PloS one 20120101

Title: Equine multiple acyl-CoA dehydrogenase deficiency (MADD) associated with seasonal pasture myopathy in the midwestern United States.

Journal: Journal of veterinary internal medicine 20120101

Title: Decreased oxidative phosphorylation and PGAM deficiency in horses suffering from atypical myopathy associated with acquired MADD.

Journal: Molecular genetics and metabolism 20111101

Title: Magnetic and mechanical anisotropy in a manganese 2-methylsuccinate framework structure.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20111024

Title: Intrinsic biodegradation potential of aromatic hydrocarbons in an alluvial aquifer--potentials and limits of signature metabolite analysis and two stable isotope-based techniques.

Journal: Water research 20111001

Title: Bcl-xL regulates metabolic efficiency of neurons through interaction with the mitochondrial F1FO ATP synthase.

Journal: Nature cell biology 20111001

Title: Contributions of dipolar relaxation processes and ionic transport to the response of liquids to electrical perturbation fields.

Journal: The journal of physical chemistry. B 20110519

Title: Ethylmalonic encephalopathy: application of improved biochemical and molecular diagnostic approaches.

Journal: Clinical genetics 20110401

Title: Phagocyte-like NADPH oxidase generates ROS in INS 832/13 cells and rat islets: role of protein prenylation.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20110301

Title: Metabolites indicate hot spots of biodegradation and biogeochemical gradients in a high-resolution monitoring well.

Journal: Environmental science & technology 20110115

Title: Glycerol/glucose co-fermentation: one more proficient process to produce propionic acid by Propionibacterium acidipropionici.

Journal: Current microbiology 20110101

Title: Risk factors of ocular involvement in children with mitochondrial respiratory chain complex defect.

Journal: Korean journal of pediatrics 20101201

Title: Streamlined pentafluorophenylpropyl column liquid chromatography-tandem quadrupole mass spectrometry and global (13)C-labeled internal standards improve performance for quantitative metabolomics in bacteria.

Journal: Journal of chromatography. A 20101119

Title: Albumin uptake in OK cells exposed to rotenone: a model for studying the effects of mitochondrial dysfunction on endocytosis in the proximal tubule?

Journal: Nephron. Physiology 20100601

Title: Mechanism of neurodegeneration of neurons with mitochondrial DNA mutations.

Journal: Brain : a journal of neurology 20100301

Title: Effect of asafoetida extract on growth and quality of Pleurotus ferulic.

Journal: International journal of molecular sciences 20100101

Title: A systems biology approach uncovers cellular strategies used by Methylobacterium extorquens AM1 during the switch from multi- to single-carbon growth.

Journal: PloS one 20100101

Title: Genome sequence of the deltaproteobacterial strain NaphS2 and analysis of differential gene expression during anaerobic growth on naphthalene.

Journal: PloS one 20100101

Title: Abnormal tricarboxylic acid cycle metabolites in isovaleric acidaemia.

Journal: Journal of inherited metabolic disease 20090601

Title: Absolute configuration of ceriporic acids, the iron redox-silencing metabolites produced by a selective lignin-degrading fungus, Ceriporiopsis subvermispora.

Journal: Chemistry and physics of lipids 20090601

Title: Global phenotypic characterization of bacteria.

Journal: FEMS microbiology reviews 20090101

Title: Start-up strategies of thermophilic anaerobic digestion of sewage sludge.

Journal: Water science and technology : a journal of the International Association on Water Pollution Research 20090101

Title: Glucagon-like peptide-1 induced signaling and insulin secretion do not drive fuel and energy metabolism in primary rodent pancreatic beta-cells.

Journal: PloS one 20090101

Title: Important discoveries from analysing bacterial phenotypes.

Journal: Molecular microbiology 20081001

Title: Anaerobic metabolic models for phosphorus- and glycogen-accumulating organisms with mixed acetic and propionic acids as carbon sources.

Journal: Water research 20080801

Title: Acquired multiple Acyl-CoA dehydrogenase deficiency in 10 horses with atypical myopathy.

Journal: Neuromuscular disorders : NMD 20080501

Title: Identification of transport pathways for citric acid cycle intermediates in the human colon carcinoma cell line, Caco-2.

Journal: Biochimica et biophysica acta 20080401

Title: Methane as fuel for anaerobic microorganisms.

Journal: Annals of the New York Academy of Sciences 20080301

Title: Organic acid concentrations in amniotic fluid found in normal and Down syndrome pregnancies.

Journal: Fetal diagnosis and therapy 20080201

Title: Fluorescence determination of N-acetylaspartic acid in the rat cerebrum homogenate using high-performance liquid chromatography with pre-column fluorescence derivatization.

Journal: Biomedical chromatography : BMC 20080101

Title: Metabolic modelling of polyhydroxyalkanoate copolymers production by mixed microbial cultures.

Journal: BMC systems biology 20080101

Title: Stereocomplementary bioreduction of alpha,beta-unsaturated dicarboxylic acids and dimethyl esters using enoate reductases: enzyme- and substrate-based stereocontrol.

Journal: Organic letters 20071220

Title: Equine biochemical multiple acyl-CoA dehydrogenase deficiency (MADD) as a cause of rhabdomyolysis.

Journal: Molecular genetics and metabolism 20070801

Title: Enhanced mitochondrial metabolism may account for the adaptation to insulin resistance in islets from C57BL/6J mice fed a high-fat diet.

Journal: Diabetologia 20070101

Title: Classical polarization in hybrid QM/MM methods.

Journal: The journal of physical chemistry. A 20060525

Title: Fumarate reductase: structural and mechanistic insights from the catalytic reduction of 2-methylfumarate.

Journal: FEBS letters 20060306

Title: Phase changes during hygroscopic cycles of mixed organic/inorganic model systems of tropospheric aerosols.

Journal: The journal of physical chemistry. A 20060209

Title: Development of an HPLC-fluorescence determination method for carboxylic acids related to the tricarboxylic acid cycle as a metabolome tool.

Journal: Biomedical chromatography : BMC 20051201

Title: Acyl-CoA dehydrogenase deficiency: varieties with neurological involvement.

Journal: Developmental medicine and child neurology 20050301

Title: D-Serine-induced nephrotoxicity: a HPLC-TOF/MS-based metabonomics approach.

Journal: Toxicology 20050214

Title: Vitamin E analogues as inducers of apoptosis: structure-function relation.

Journal: British journal of cancer 20030616

Title: Organic anion transporter 3 (Slc22a8) is a dicarboxylate exchanger indirectly coupled to the Na+ gradient.

Journal: American journal of physiology. Renal physiology 20030401

Title: Human renal organic anion transporter 1-dependent uptake and toxicity of mercuric-thiol conjugates in Madin-Darby canine kidney cells.

Journal: Molecular pharmacology 20030301

Title: Ethylmalonic encephalopathy: further clinical and neuroradiological characterization.

Journal: Journal of neurology 20021001

Title: Microsphaerones A and B, two novel gamma-pyrone derivatives from the sponge-derived fungus Microsphaeropsis sp.

Journal: Journal of natural products 20020501

Title: A constitutive nitric oxide synthase modulates insulin secretion in the INS-1 cell line.

Journal: Molecular and cellular endocrinology 20011025

Title: Antimalarial halorosellinic acid from the marine fungus Halorosellinia oceanica.

Journal: Bioorganic & medicinal chemistry letters 20010806

Title: Grosso S, et al. Ethylmalonic encephalopathy: further clinical and neuroradiological characterization. J Neurol. 2002 Oct;249(10):1446-50.

Title: Nowaczyk MJ, et al. Ethylmalonic and methylsuccinic aciduria in ethylmalonic encephalopathy arise from abnormal isoleucine metabolism. Metabolism. 1998 Jul;47(7):836-9.

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SDS
Tags:498-21-5 Molecular Formula|498-21-5 MDL|498-21-5 SMILES|498-21-5 Methylsuccinic acid
Catalog No.: AA003279
498-21-5,MFCD00002659
498-21-5 | Methylsuccinic acid
Pack Size: 5g
Purity: 95%
in stock
$8.00 $6.00
Pack Size: 10g
Purity: 95%
in stock
$10.00 $7.00
Pack Size: 25g
Purity: 95%
in stock
$22.00 $16.00
Pack Size: 100g
Purity: 95%
in stock
$66.00 $46.00
Quantity
- +
Add to Card
Order Now
bulk Quotation Request
Technical Information
Catalog Number: AA003279
Chemical Name: Methylsuccinic acid
CAS Number: 498-21-5
Molecular Formula: C5H8O4
Molecular Weight: 132.1146
MDL Number: MFCD00002659
SMILES: OC(=O)CC(C(=O)O)C
NSC Number: 5276
Properties
BP: 236.5 °C at 760 mmHg  
Form: Solid  
MP: 110-115 °C  
Refractive Index: 1.4240 (estimate)  
Storage: Keep in dry area;Room Temperature;  
Complexity: 129  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 0  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 9  
Hydrogen Bond Acceptor Count: 4  
Hydrogen Bond Donor Count: 2  
Isotope Atom Count: 0  
Rotatable Bond Count: 3  
Undefined Atom Stereocenter Count: 1  
Undefined Bond Stereocenter Count: 0  
XLogP3: -0.2  
Literature fold

Title: Urinary Time- or Dose-Dependent Metabolic Biomarkers of Aristolochic Acid-Induced Nephrotoxicity in Rats.

Journal: Toxicological sciences : an official journal of the Society of Toxicology20170301

Title: Cannabinoid receptor antagonist-induced striated muscle toxicity and ethylmalonic-adipic aciduria in beagle dogs.

Journal: Toxicological sciences : an official journal of the Society of Toxicology20121001

Title: Biochemical, molecular, and clinical characteristics of children with short chain acyl-CoA dehydrogenase deficiency detected by newborn screening in California.

Journal: Molecular genetics and metabolism20120501

Title: A temporal-omic study of Propionibacterium freudenreichii CIRM-BIA1 adaptation strategies in conditions mimicking cheese ripening in the cold.

Journal: PloS one20120101

Title: M19 modulates skeletal muscle differentiation and insulin secretion in pancreatic β-cells through modulation of respiratory chain activity.

Journal: PloS one20120101

Title: Dopamine induced neurodegeneration in a PINK1 model of Parkinson's disease.

Journal: PloS one20120101

Title: Equine multiple acyl-CoA dehydrogenase deficiency (MADD) associated with seasonal pasture myopathy in the midwestern United States.

Journal: Journal of veterinary internal medicine20120101

Title: Decreased oxidative phosphorylation and PGAM deficiency in horses suffering from atypical myopathy associated with acquired MADD.

Journal: Molecular genetics and metabolism20111101

Title: Magnetic and mechanical anisotropy in a manganese 2-methylsuccinate framework structure.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany)20111024

Title: Intrinsic biodegradation potential of aromatic hydrocarbons in an alluvial aquifer--potentials and limits of signature metabolite analysis and two stable isotope-based techniques.

Journal: Water research20111001

Title: Bcl-xL regulates metabolic efficiency of neurons through interaction with the mitochondrial F1FO ATP synthase.

Journal: Nature cell biology20111001

Title: Contributions of dipolar relaxation processes and ionic transport to the response of liquids to electrical perturbation fields.

Journal: The journal of physical chemistry. B20110519

Title: Ethylmalonic encephalopathy: application of improved biochemical and molecular diagnostic approaches.

Journal: Clinical genetics20110401

Title: Phagocyte-like NADPH oxidase generates ROS in INS 832/13 cells and rat islets: role of protein prenylation.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology20110301

Title: Metabolites indicate hot spots of biodegradation and biogeochemical gradients in a high-resolution monitoring well.

Journal: Environmental science & technology20110115

Title: Glycerol/glucose co-fermentation: one more proficient process to produce propionic acid by Propionibacterium acidipropionici.

Journal: Current microbiology20110101

Title: Risk factors of ocular involvement in children with mitochondrial respiratory chain complex defect.

Journal: Korean journal of pediatrics20101201

Title: Streamlined pentafluorophenylpropyl column liquid chromatography-tandem quadrupole mass spectrometry and global (13)C-labeled internal standards improve performance for quantitative metabolomics in bacteria.

Journal: Journal of chromatography. A20101119

Title: Albumin uptake in OK cells exposed to rotenone: a model for studying the effects of mitochondrial dysfunction on endocytosis in the proximal tubule?

Journal: Nephron. Physiology20100601

Title: Mechanism of neurodegeneration of neurons with mitochondrial DNA mutations.

Journal: Brain : a journal of neurology20100301

Title: Effect of asafoetida extract on growth and quality of Pleurotus ferulic.

Journal: International journal of molecular sciences20100101

Title: A systems biology approach uncovers cellular strategies used by Methylobacterium extorquens AM1 during the switch from multi- to single-carbon growth.

Journal: PloS one20100101

Title: Genome sequence of the deltaproteobacterial strain NaphS2 and analysis of differential gene expression during anaerobic growth on naphthalene.

Journal: PloS one20100101

Title: Abnormal tricarboxylic acid cycle metabolites in isovaleric acidaemia.

Journal: Journal of inherited metabolic disease20090601

Title: Absolute configuration of ceriporic acids, the iron redox-silencing metabolites produced by a selective lignin-degrading fungus, Ceriporiopsis subvermispora.

Journal: Chemistry and physics of lipids20090601

Title: Global phenotypic characterization of bacteria.

Journal: FEMS microbiology reviews20090101

Title: Start-up strategies of thermophilic anaerobic digestion of sewage sludge.

Journal: Water science and technology : a journal of the International Association on Water Pollution Research20090101

Title: Glucagon-like peptide-1 induced signaling and insulin secretion do not drive fuel and energy metabolism in primary rodent pancreatic beta-cells.

Journal: PloS one20090101

Title: Important discoveries from analysing bacterial phenotypes.

Journal: Molecular microbiology20081001

Title: Anaerobic metabolic models for phosphorus- and glycogen-accumulating organisms with mixed acetic and propionic acids as carbon sources.

Journal: Water research20080801

Title: Acquired multiple Acyl-CoA dehydrogenase deficiency in 10 horses with atypical myopathy.

Journal: Neuromuscular disorders : NMD20080501

Title: Identification of transport pathways for citric acid cycle intermediates in the human colon carcinoma cell line, Caco-2.

Journal: Biochimica et biophysica acta20080401

Title: Methane as fuel for anaerobic microorganisms.

Journal: Annals of the New York Academy of Sciences20080301

Title: Organic acid concentrations in amniotic fluid found in normal and Down syndrome pregnancies.

Journal: Fetal diagnosis and therapy20080201

Title: Fluorescence determination of N-acetylaspartic acid in the rat cerebrum homogenate using high-performance liquid chromatography with pre-column fluorescence derivatization.

Journal: Biomedical chromatography : BMC20080101

Title: Metabolic modelling of polyhydroxyalkanoate copolymers production by mixed microbial cultures.

Journal: BMC systems biology20080101

Title: Stereocomplementary bioreduction of alpha,beta-unsaturated dicarboxylic acids and dimethyl esters using enoate reductases: enzyme- and substrate-based stereocontrol.

Journal: Organic letters20071220

Title: Equine biochemical multiple acyl-CoA dehydrogenase deficiency (MADD) as a cause of rhabdomyolysis.

Journal: Molecular genetics and metabolism20070801

Title: Enhanced mitochondrial metabolism may account for the adaptation to insulin resistance in islets from C57BL/6J mice fed a high-fat diet.

Journal: Diabetologia20070101

Title: Classical polarization in hybrid QM/MM methods.

Journal: The journal of physical chemistry. A20060525

Title: Fumarate reductase: structural and mechanistic insights from the catalytic reduction of 2-methylfumarate.

Journal: FEBS letters20060306

Title: Phase changes during hygroscopic cycles of mixed organic/inorganic model systems of tropospheric aerosols.

Journal: The journal of physical chemistry. A20060209

Title: Development of an HPLC-fluorescence determination method for carboxylic acids related to the tricarboxylic acid cycle as a metabolome tool.

Journal: Biomedical chromatography : BMC20051201

Title: Acyl-CoA dehydrogenase deficiency: varieties with neurological involvement.

Journal: Developmental medicine and child neurology20050301

Title: D-Serine-induced nephrotoxicity: a HPLC-TOF/MS-based metabonomics approach.

Journal: Toxicology20050214

Title: Vitamin E analogues as inducers of apoptosis: structure-function relation.

Journal: British journal of cancer20030616

Title: Organic anion transporter 3 (Slc22a8) is a dicarboxylate exchanger indirectly coupled to the Na+ gradient.

Journal: American journal of physiology. Renal physiology20030401

Title: Human renal organic anion transporter 1-dependent uptake and toxicity of mercuric-thiol conjugates in Madin-Darby canine kidney cells.

Journal: Molecular pharmacology20030301

Title: Ethylmalonic encephalopathy: further clinical and neuroradiological characterization.

Journal: Journal of neurology20021001

Title: Microsphaerones A and B, two novel gamma-pyrone derivatives from the sponge-derived fungus Microsphaeropsis sp.

Journal: Journal of natural products20020501

Title: A constitutive nitric oxide synthase modulates insulin secretion in the INS-1 cell line.

Journal: Molecular and cellular endocrinology20011025

Title: Antimalarial halorosellinic acid from the marine fungus Halorosellinia oceanica.

Journal: Bioorganic & medicinal chemistry letters20010806

Title: Grosso S, et al. Ethylmalonic encephalopathy: further clinical and neuroradiological characterization. J Neurol. 2002 Oct;249(10):1446-50.

Title: Nowaczyk MJ, et al. Ethylmalonic and methylsuccinic aciduria in ethylmalonic encephalopathy arise from abnormal isoleucine metabolism. Metabolism. 1998 Jul;47(7):836-9.

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