601-75-2 | Ethylmalonic acid

Packsize	Purity	Availability	Price	Discounted Price
5g	98%	in stock	$15.00	$10.00
10g	98%	in stock	$25.00	$17.00
100g	98%	in stock	$158.00	$110.00
500g	98%	in stock	$620.00	$434.00

Description

• Catalog Number: AB44046
• Chemical Name: Ethylmalonic acid
• CAS Number: 601-75-2
• Molecular Formula: C5H8O4
• Molecular Weight: 132.1146
• MDL Number: MFCD00002668
• SMILES: CCC(C(=O)O)C(=O)O
• NSC Number: 96615

Computed Properties

• Complexity: 115
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 9
• Hydrogen Bond Acceptor Count: 4
• Hydrogen Bond Donor Count: 2
• Rotatable Bond Count: 3
• XLogP3: 0.4

Upstream Synthesis Route

2-Ethylmalonic acid is a versatile compound widely used in chemical synthesis due to its unique properties. In organic chemistry, it serves as a key building block for the synthesis of various pharmaceuticals, agrochemicals, and fine chemicals. Specifically, 2-Ethylmalonic acid is commonly utilized as a precursor in the production of chiral molecules and heterocycles, contributing to the development of novel therapies and functional materials. Additionally, its reactive functional groups make it an important intermediate in the synthesis of complex organic compounds, enabling chemists to access diverse molecular structures efficiently. Overall, the application of 2-Ethylmalonic acid in chemical synthesis plays a crucial role in advancing the field of organic chemistry and facilitating the creation of innovative products.

Literature

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

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

• Arabidopsis ETHE1 encodes a sulfur dioxygenase that is essential for embryo and endosperm development.

  Plant physiology 20120901

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

  Molecular genetics and metabolism 20120501

• Ethylmalonic acid impairs brain mitochondrial succinate and malate transport.

  Molecular genetics and metabolism 20120101

• Ethylmalonyl-CoA decarboxylase, a new enzyme involved in metabolite proofreading.

  The Journal of biological chemistry 20111216

• Synthesis, structural analysis, and magnetic properties of ethylmalonate-manganese(II) complexes.

  Inorganic chemistry 20111107

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

  Molecular genetics and metabolism 20111101

• Biochemical diagnosis of mitochondrial disorders.

  Journal of inherited metabolic disease 20110401

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

  Clinical genetics 20110401

• Toxic response caused by a misfolding variant of the mitochondrial protein short-chain acyl-CoA dehydrogenase.

  Journal of inherited metabolic disease 20110401

• Brown-Vialetto-Van Laere and Fazio Londe syndrome is associated with a riboflavin transporter defect mimicking mild MADD: a new inborn error of metabolism with potential treatment.

  Journal of inherited metabolic disease 20110201

• Mutations of ACADS gene associated with short-chain acyl-coenzyme A dehydrogenase deficiency.

  Annals of clinical and laboratory science 20110101

• Clinical and neuropathological picture of ethylmalonic aciduria - diagnostic dilemma.

  Folia neuropathologica 20110101

• Vulnerability to oxidative stress in vitro in pathophysiology of mitochondrial short-chain acyl-CoA dehydrogenase deficiency: response to antioxidants.

  PloS one 20110101

• Efficacy and outcome of expanded newborn screening for metabolic diseases--report of 10 years from South-West Germany.

  Orphanet journal of rare diseases 20110101

• Ethylene glycol monomethyl ether-induced toxicity is mediated through the inhibition of flavoprotein dehydrogenase enzyme family.

  Toxicological sciences : an official journal of the Society of Toxicology 20101201

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

  Korean journal of pediatrics 20101201

• 6-[Bis(ethoxycarbonyl)methyl]-6-deoxy-1,2;3,4-di-O-isopropyl-idene-d-galacto-pyran-ose.

  Acta crystallographica. Section E, Structure reports online 20101201

• Clinical aspects of short-chain acyl-CoA dehydrogenase deficiency.

  Journal of inherited metabolic disease 20101001

• Pathogenesis and treatment of mitochondrial myopathies: recent advances.

  Acta myologica : myopathies and cardiomyopathies : official journal of the Mediterranean Society of Myology 20101001

• Combined treatment with oral metronidazole and N-acetylcysteine is effective in ethylmalonic encephalopathy.

  Nature medicine 20100801

• Antioxidant dysfunction: potential risk for neurotoxicity in ethylmalonic aciduria.

  Journal of inherited metabolic disease 20100601

• Silent increase of urinary ethylmalonic acid is an indicator of nonspecific brain dysfunction.

  NMR in biomedicine 20100501

• Flavin adenine dinucleotide status and the effects of high-dose riboflavin treatment in short-chain acyl-CoA dehydrogenase deficiency.

  Pediatric research 20100301

• Promotion of lipid and protein oxidative damage in rat brain by ethylmalonic acid.

  Neurochemical research 20100201

• Fasting and fat-loading tests provide pathophysiological insight into short-chain acyl-coenzyme a dehydrogenase deficiency.

  The Journal of pediatrics 20100101

• Inborn errors of energy metabolism associated with myopathies.

  Journal of biomedicine & biotechnology 20100101

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

  PloS one 20100101

• Chronic early postnatal administration of ethylmalonic acid to rats causes behavioral deficit.

  Behavioural brain research 20090211

• Loss of ETHE1, a mitochondrial dioxygenase, causes fatal sulfide toxicity in ethylmalonic encephalopathy.

  Nature medicine 20090201

• Short-chain acyl-coenzyme A dehydrogenase deficiency.

  Molecular genetics and metabolism 20081201

• The ACADS gene variation spectrum in 114 patients with short-chain acyl-CoA dehydrogenase (SCAD) deficiency is dominated by missense variations leading to protein misfolding at the cellular level.

  Human genetics 20080801

• 2-(4-Ethoxy-benzyl-idene)butanoic acid.

  Acta crystallographica. Section E, Structure reports online 20080801

• [Short-chain acyl-CoA dehydrogenase deficiency (SCADD): relatively high prevalence in the Netherlands and strongly variable fenotype; neonatal screening not indicated].

  Nederlands tijdschrift voor geneeskunde 20080726

• Severe infantile hypotonia with ethylmalonic aciduria: case report.

  Journal of child neurology 20080601

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

  Neuromuscular disorders : NMD 20080501

• (E)-2-(2-Fluoro-benzyl-idene)butanoic acid.

  Acta crystallographica. Section E, Structure reports online 20080401

• A new case of short-chain acyl-CoA dehydrogenase deficiency: clinical, biochemical, genetic and (1)H-NMR spectroscopic studies.

  Neurological sciences : official journal of the Italian Neurological Society and of the Italian Society of Clinical Neurophysiology 20071201

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

  Molecular genetics and metabolism 20070801

• Lessons to learn from rare inborn errors of metabolism.

  Neuropediatrics 20070401

• Ethylmalonic encephalopathy: clinical and biochemical observations.

  Neuropediatrics 20070401

• Development of a newborn screening follow-up algorithm for the diagnosis of isobutyryl-CoA dehydrogenase deficiency.

  Genetics in medicine : official journal of the American College of Medical Genetics 20070201

• Single-nucleotide variations in the genes encoding the mitochondrial Hsp60/Hsp10 chaperone system and their disease-causing potential.

  Journal of human genetics 20070101

• Taxonomic revision of Aspergillus section Clavati based on molecular, morphological and physiological data.

  Studies in mycology 20070101

• A case of ethylmalonic encephalopathy with atypical clinical and biochemical presentation.

  Molecular genetics and metabolism 20061201

• Persistent increase of plasma butyryl/isobutyrylcarnitine concentrations as marker of SCAD defect and ethylmalonic encephalopathy.

  Journal of inherited metabolic disease 20061001

• Clinical, biochemical, and genetic heterogeneity in short-chain acyl-coenzyme A dehydrogenase deficiency.

  JAMA 20060823

• Ethylmalonic encephalopathy-report of two cases.

  Brain & development 20060601

• ETHE1 mutations are specific to ethylmalonic encephalopathy.

  Journal of medical genetics 20060401

• Metabolomic and bioinformatic analyses in asphyxiated neonates.

  Clinical biochemistry 20060301

• Inhibition of the electron transport chain and creatine kinase activity by ethylmalonic acid in human skeletal muscle.

  Metabolic brain disease 20060301

• Effect of in vivo administration of ethylmalonic acid on energy metabolism in rat tissues.

  Metabolic brain disease 20060301

• Perioperative management of a child with short-chain acyl-CoA dehydrogenase deficiency.

  Paediatric anaesthesia 20050901

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

  Developmental medicine and child neurology 20050301

• Clinical, biochemical, magnetic resonance imaging (MRI) and proton magnetic resonance spectroscopy (1H MRS) findings in a fourth case of combined D- and L-2 hydroxyglutaric aciduria.

  Journal of inherited metabolic disease 20050101

• The putative elaiophylin biosynthetic gene cluster in Streptomyces sp. DSM4137 is adjacent to genes encoding adenosylcobalamin-dependent methylmalonyl CoA mutase and to genes for synthesis of cobalamin.

  Journal of biotechnology 20040930

• Recent developments and new applications of tandem mass spectrometry in newborn screening.

  Current opinion in pediatrics 20040801

• The role of methionine in ethylmalonic encephalopathy with petechiae.

  Archives of neurology 20040401

• Ethylmalonic encephalopathy is caused by mutations in ETHE1, a gene encoding a mitochondrial matrix protein.

  American journal of human genetics 20040201

• [Late-onset riboflavin-responsive multiple acyl-CoA dehydrogenase deficiency (glutaric aciduria type II)].

  Zhonghua er ke za zhi = Chinese journal of pediatrics 20031201

• A comparison of in vitro acylcarnitine profiling methods for the diagnosis of classical and variant short chain acyl-CoA dehydrogenase deficiency.

  Clinica chimica acta; international journal of clinical chemistry 20031101

• Short-chain Acyl-CoA dehydrogenase deficiency: studies in a large family adding to the complexity of the disorder.

  Pediatrics 20031101

• Ethylmalonic acid inhibits mitochondrial creatine kinase activity from cerebral cortex of young rats in vitro.

  Neurochemical research 20030501

• Structure-based design of inhibitors of human L-xylulose reductase modelled into the active site of the enzyme.

  Bioorganic & medicinal chemistry letters 20030417

• Recurrent vomiting and ethylmalonic aciduria associated with rare mutations of the short-chain acyl-CoA dehydrogenase gene.

  Journal of inherited metabolic disease 20030101

• Mutation analysis of copper transporter genes in patients with ethylmalonic encephalopathy, mitochondriopathies and copper deficiency phenotypes.

  Journal of inherited metabolic disease 20030101

• Inhibition of creatine kinase activity in vitro by ethylmalonic acid in cerebral cortex of young rats.

  Neurochemical research 20021201

• Ethylmalonic encephalopathy: further clinical and neuroradiological characterization.

  Journal of neurology 20021001

• Purification and characterization of two polymorphic variants of short chain acyl-CoA dehydrogenase reveal reduction of catalytic activity and stability of the Gly185Ser enzyme.

  Biochemistry 20020917

• Hypoglycaemia and elevated urine ethylmalonic acid in a child homozygous for the short-chain acyl-CoA dehydrogenase 625G > A gene variation.

  Acta paediatrica (Oslo, Norway : 1992) 20020101

• Therapeutic trial in the first three Asian cases of ethylmalonic encephalopathy: response to riboflavin.

  Journal of inherited metabolic disease 20011201

• Artefactual pyruvate and 2-oxobutyrate produced by trimethylsilylation of methylmalonic and ethylmalonic acids in the presence of oxygen.

  Journal of inherited metabolic disease 19991001