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97-65-4 | 2-Methylenesuccinic acid
CAS No: 97-65-4 Catalog No: AG003R5X MDL No:MFCD00004260
Product Description
Catalog Number:
AG003R5X
Chemical Name:
2-Methylenesuccinic acid
CAS Number:
97-65-4
Molecular Formula:
C5H6O4
Molecular Weight:
130.0987
MDL Number:
MFCD00004260
IUPAC Name:
2-methylidenebutanedioic acid
InChI:
InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9)
InChI Key:
LVHBHZANLOWSRM-UHFFFAOYSA-N
SMILES:
OC(=O)CC(=C)C(=O)O
EC Number:
202-599-6
UNII:
Q4516562YH
NSC Number:
3357
Properties
Complexity:
158
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
130.027g/mol
Formal Charge:
0
Heavy Atom Count:
9
Hydrogen Bond Acceptor Count:
4
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
130.099g/mol
Monoisotopic Mass:
130.027g/mol
Rotatable Bond Count:
3
Topological Polar Surface Area:
74.6A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.1
Literature
| Title | Journal |
|---|---|
| Electrophilic properties of itaconate and derivatives regulate the IκBζ-ATF3 inflammatory axis. | Nature 20180401 |
| Genetic and biochemical insights into the itaconate pathway of Ustilago maydis enable enhanced production. | Metabolic engineering 20161101 |
| Itaconate Links Inhibition of Succinate Dehydrogenase with Macrophage Metabolic Remodeling and Regulation of Inflammation. | Cell metabolism 20160712 |
| Abolition of mitochondrial substrate-level phosphorylation by itaconic acid produced by LPS-induced Irg1 expression in cells of murine macrophage lineage. | FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20160101 |
| Inhibitors of the glyoxylate cycle enzyme ICL1 in Candida albicans for potential use as antifungal agents. | PloS one 20140101 |
| Controlled release of lipase from Candida rugosa loaded into hydrogels of N-isopropylacrylamide and itaconic acid. | International journal of pharmaceutics 20121015 |
| Preliminary assessment of the safety evaluation of novel pH-sensitive hydrogel. | European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V 20121001 |
| Microbial Community-Level Physiological Profiles (CLPP) and herbicide mineralization potential in groundwater affected by agricultural land use. | Journal of contaminant hydrology 20121001 |
| Analysis and quantification of ammonia-oxidizing bacteria community with amoA gene in sewage treatment plants. | Journal of microbiology and biotechnology 20120901 |
| Resin zirconia bonding promotion with some novel coupling agents. | Dental materials : official publication of the Academy of Dental Materials 20120801 |
| Molecular imprinting solid phase extraction for selective detection of methidathion in olive oil. | Analytica chimica acta 20120713 |
| Removal of cyanotoxins from surface water resources using reusable molecularly imprinted polymer adsorbents. | Environmental science and pollution research international 20120601 |
| Synthesis and characterization of thermo- and pH-sensitive poly(vinyl alcohol)/poly(N, N-diethylacrylamide-co-itaconic acid) semi-IPN hydrogels. | Biomedical materials (Bristol, England) 20120601 |
| Parallel synthesis of 2-substituted 6-(5-oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxamides. | Molecules (Basel, Switzerland) 20120508 |
| Elevated cytokinin content in ipt transgenic creeping bentgrass promotes drought tolerance through regulating metabolite accumulation. | Journal of experimental botany 20120201 |
| Phenotypic characterization and 16S rDNA identification of culturable non-obligate halophilic bacterial communities from a hypersaline lake, La Sal del Rey, in extreme South Texas (USA). | Aquatic biosystems 20120101 |
| Biomass pretreatment affects Ustilago maydis in producing itaconic acid. | Microbial cell factories 20120101 |
| Enhanced itaconic acid production in Aspergillus niger using genetic modification and medium optimization. | BMC biotechnology 20120101 |
| Stitching phospholanes together piece by piece: new modular di- and tridentate stereodirecting ligands. | Chemistry (Weinheim an der Bergstrasse, Germany) 20111209 |
| Itaconic acid is a mammalian metabolite induced during macrophage activation. | Journal of the American Chemical Society 20111019 |
| Selective homogeneous hydrogenation of biogenic carboxylic acids with [Ru(TriPhos)H]+: a mechanistic study. | Journal of the American Chemical Society 20110914 |
| Sorption of zinc by novel pH-sensitive hydrogels based on chitosan, itaconic acid and methacrylic acid. | Journal of hazardous materials 20110830 |
| New species in Aspergillus section Terrei. | Studies in mycology 20110630 |
| A clone-based transcriptomics approach for the identification of genes relevant for itaconic acid production in Aspergillus. | Fungal genetics and biology : FG & B 20110601 |
| Itaconic acid derivatives and diketopiperazine from the marine-derived fungus Aspergillus aculeatus CRI322-03. | Phytochemistry 20110601 |
| Effects of N-vinylcaprolactam containing polyelectrolytes on hardness, fluoride release and water sorption of conventional glass ionomers. | The Journal of prosthetic dentistry 20110501 |
| Biobased poly(propylene sebacate) as shape memory polymer with tunable switching temperature for potential biomedical applications. | Biomacromolecules 20110411 |
| Preparation and evaluation of a monolithic molecularly imprinted polymer for the chiral separation of neurotransmitters and their analogues by capillary electrochromatography. | Journal of chromatography. A 20110211 |
| Anthrolysin O and fermentation products mediate the toxicity of Bacillus anthracis to lung epithelial cells under microaerobic conditions. | FEMS immunology and medical microbiology 20110201 |
| Metabolic engineering of Escherichia coli for biotechnological production of high-value organic acids and alcohols. | Applied microbiology and biotechnology 20110201 |
| Synthesis and study of a molecularly imprinted polymer for the specific extraction of indole alkaloids from Catharanthus roseus extracts. | Analytica chimica acta 20110110 |
| Posttranslational modification of 6-phosphofructo-1-kinase as an important feature of cancer metabolism. | PloS one 20110101 |
| Natural-synthetic hybrid polymers developed via electrospinning: the effect of PET in chitosan/starch system. | International journal of molecular sciences 20110101 |
| Characterization of Lovastatin biosynthetic cluster proteins in Aspergillus terreus strain ATCC 20542. | Bioinformation 20110101 |
| Synthesis characterization and biological activity study of new schiff and mannich bases and some metal complexes derived from isatin and dithiooxamide. | Bioinorganic chemistry and applications 20110101 |
| Bacterial and archaea community present in the Pine Barrens Forest of Long Island, NY: unusually high percentage of ammonia oxidizing bacteria. | PloS one 20110101 |
| Enzyme-polymers conjugated to quantum-dots for sensing applications. | Sensors (Basel, Switzerland) 20110101 |
| Metal ion mediated molecularly imprinted polymer for selective capturing antibiotics containing beta-diketone structure. | Journal of chromatography. A 20101224 |
| Gluconic acid production by Aspergillus terreus. | Letters in applied microbiology 20100901 |
| Chemical profiling of lentil (Lens culinaris Medik.) Cultivars and isolation of compounds. | Journal of agricultural and food chemistry 20100811 |
| One-pot synthesis of functionalized 4-oxo-2-thioxo-1,3-thiazinanes from primary amines, CS(2), and itaconic anhydride. | Molecular diversity 20100801 |
| Enhancing itaconic acid production by Aspergillus terreus. | Applied microbiology and biotechnology 20100801 |
| Selective and flexible transformation of biomass-derived platform chemicals by a multifunctional catalytic system. | Angewandte Chemie (International ed. in English) 20100726 |
| Solvent retention of contemporary commercial dentin bonding agents in a demineralized dentin matrix. | European journal of dentistry 20100701 |
| Molecularly imprinted polymers for ochratoxin a extraction and analysis. | Toxins 20100601 |
| Surface characterization of functionalized latexes with different surface functionalities using rheometry and dynamic light scattering. | Journal of colloid and interface science 20100515 |
| Influence of unsaturated carbonic acids on hemocompatibility and cytotoxicity of poly-vinylacetate based co-polymers. | Journal of materials science. Materials in medicine 20100501 |
| Reactivity ratios for organotin copolymer systems. | Molecules (Basel, Switzerland) 20100415 |
| Characterization of pH-responsive hydrogels of poly(itaconic acid-g-ethylene glycol) prepared by UV-initiated free radical polymerization as biomaterials for oral delivery of bioactive agents. | Journal of biomedical materials research. Part A 20100401 |
| Hydrogels of N-isopropylacrylamide copolymers with controlled release of a model protein. | International journal of pharmaceutics 20100104 |
| Rational design and study on recognition property of paracetamol-imprinted polymer. | Applied biochemistry and biotechnology 20100101 |
| Hydroxyapatite crystals biologically inspired on titanium by using an organic template based on the copolymer of acrylic acid and itaconic acid. | Journal of biomedical materials research. Part A 20100101 |
| Isolation of an oxalate-resistant Ashbya gossypii strain and its improved riboflavin production. | Journal of industrial microbiology & biotechnology 20100101 |
| Effect of Using Electric Current during Dentin Bonding Agent Application on Microleakage under Simulated Pulpal Pressure Condition. | Dental research journal 20100101 |
| Enantioselective protonation of itaconimides with thiols and the rotational kinetics of the axially chiral C-N bond. | Chemistry, an Asian journal 20091102 |
| Swelling properties of copolymeric hydrogels of poly(ethylene glycol) monomethacrylate and monoesters of itaconic acid for use in drug delivery. | Journal of biomedical materials research. Part B, Applied biomaterials 20091101 |
| Aspergillus terreus NADP-glutamate dehydrogenase is kinetically distinct from the allosteric enzyme of other Aspergilli. | Mycological research 20091001 |
| A novel monoclonal antibody specific to peptide pdnaelvlltlgqawqg. | Hybridoma (2005) 20091001 |
| Anaerobic central metabolic pathways active during polyhydroxyalkanoate production in uncultured cluster 1 Defluviicoccus enriched in activated sludge communities. | FEMS microbiology letters 20090901 |
| Biotechnological production of itaconic acid and its biosynthesis in Aspergillus terreus. | Applied microbiology and biotechnology 20090901 |
| Induction of membrane permeability in Escherichia coli mediated by lysis protein of the ColE7 operon. | FEMS microbiology letters 20090901 |
| Acrylamide-sepiolite based composite hydrogels for immobilization of invertase. | Journal of food science 20090901 |
| Catalytic (transfer) deuterogenation in D2O as deuterium source with H2 and HCO2H as electron sources. | Dalton transactions (Cambridge, England : 2003) 20090828 |
| Crystal structure and putative mechanism of 3-methylitaconate-delta-isomerase from Eubacterium barkeri. | Journal of molecular biology 20090821 |
| Characterization of leaf apoplastic peroxidases and metabolites in Vigna unguiculata in response to toxic manganese supply and silicon. | Journal of experimental botany 20090401 |
| Imprinted polymers for chiral resolution of (+/-)-ephedrine. Part 3: NMR predictions and HPLC results with alternative functional monomers. | The Analyst 20090301 |
| Three lanthanide complexes derived from itaconic acid and 2,2'-bipyridine. | Acta crystallographica. Section C, Crystal structure communications 20090301 |
| Synthesis and characterization of a novel fast-set proline-derivative-containing glass ionomer cement with enhanced mechanical properties. | Acta biomaterialia 20090101 |
| Property changes of powdery polyacrylonitrile synthesized by aqueous suspension polymerization during heat-treatment process under air atmosphere. | Journal of colloid and interface science 20090101 |
| Virulent clones of Klebsiella pneumoniae: identification and evolutionary scenario based on genomic and phenotypic characterization. | PloS one 20090101 |
| Synthesis and properties of polycarboxylate-type green surfactants with S- or N-linkages. | Journal of oleo science 20090101 |
| The derivatization of bioplatform molecules by using KF/alumina catalysis. | ChemSusChem 20090101 |
| Clinical Performance of Viscous Glass Ionomer Cement in Posterior Cavities over Two Years. | International journal of dentistry 20090101 |
| Modification of conventional glass-ionomer cements with N-vinylpyrrolidone containing polyacids, nano-hydroxy and fluoroapatite to improve mechanical properties. | Dental materials : official publication of the Academy of Dental Materials 20081001 |
| De novo synthesis of (Z)- and (E)-7-hexadecenylitaconic acids by a selective lignin-degrading fungus, Ceriporiopsis subvermispora. | Phytochemistry 20081001 |
| Hemoglobin recognition of molecularly imprinted hydrogels prepared at different pHs. | Analytica chimica acta 20080905 |
| Cloning and functional characterization of the cis-aconitic acid decarboxylase (CAD) gene from Aspergillus terreus. | Applied microbiology and biotechnology 20080801 |
| Dihydroxystyrene metabolites from an association of the sponges Poecillastra wondoensis and Jaspis sp. | Journal of natural products 20080501 |
| Production of renewable polymers from crop plants. | The Plant journal : for cell and molecular biology 20080501 |
| Sesterterpenoids from the sponge Sarcotragus sp. | Journal of natural products 20080401 |
| Use of itaconic acid-based polymers for solid-phase extraction of deoxynivalenol and application to pasta analysis. | Analytica chimica acta 20080225 |
| Bis-(2,5-diphenylphospholanes) with sp2 carbon linkers: synthesis and application in asymmetric hydrogenation. | The Journal of organic chemistry 20080201 |
| Fluconazole release from hydrogels including acrylamide-acrylic acid-itaconic acid, and their microbiological interactions. | Journal of biomaterials science. Polymer edition 20080101 |
| Stereocomplementary bioreduction of alpha,beta-unsaturated dicarboxylic acids and dimethyl esters using enoate reductases: enzyme- and substrate-based stereocontrol. | Organic letters 20071220 |
| Itaconic acid production using sago starch hydrolysate by Aspergillus terreus TN484-M1. | Bioresource technology 20071201 |
| Asymmetric hydrogenation using monodentate phosphoramidite ligands. | Accounts of chemical research 20071201 |
| Isolation of Ashbya gossypii mutant for an improved riboflavin production targeting for biorefinery technology. | Journal of applied microbiology 20070801 |
| Effects of lactose and glucose on production of itaconic acid and lovastatin by Aspergillus terreus ATCC 20542. | Journal of bioscience and bioengineering 20070701 |
| [The drug release properties of poly (acrylamide-co-itaconate-vinylbenzylglycosylallylamide) hydrogels]. | Sheng wu yi xue gong cheng xue za zhi = Journal of biomedical engineering = Shengwu yixue gongchengxue zazhi 20070601 |
| Virtual imprinting as a tool to design efficient MIPs for photosynthesis-inhibiting herbicides. | Biosensors & bioelectronics 20070415 |
| Redox silencing of the Fenton reaction system by an alkylitaconic acid, ceriporic acid B produced by a selective lignin-degrading fungus, Ceriporiopsis subvermispora. | Organic & biomolecular chemistry 20070307 |
| Topography of the active site of the Saccharomyces cerevisiae plasmalemmal dicarboxylate transporter studied using lipophilic derivatives of its substrates. | Biochemistry. Biokhimiia 20070301 |
| Highly enantioselective hydrogenation of alpha-dehydroamino esters and itaconates with triphosphorous bidentate ligands and the unprecedented solvent effect thereof. | The Journal of organic chemistry 20070202 |
| Inverted supercritical carbon dioxide/aqueous biphasic media for rhodium-catalyzed hydrogenation reactions. | Chemistry (Weinheim an der Bergstrasse, Germany) 20070101 |
| The complete genome sequence and analysis of the epsilonproteobacterium Arcobacter butzleri. | PloS one 20070101 |
| Synthesis of UV-absorbing and fluorescent carrier ampholyte mixtures and their application for the determination of the operational pH values of buffering membranes used in isoelectric trapping separations. | Journal of chromatography. A 20061020 |
| Effect of supercritical CO2 in modified polystyrene 3D latex arrays. | Langmuir : the ACS journal of surfaces and colloids 20061010 |
| Catalytic ability of a cationic Ru(II) monochloro complex for the asymmetric hydrogenation of dimethyl itaconate and enamides. | Inorganic chemistry 20060320 |
| Factors affecting broadband acoustic emission measurements of a heterogeneous reaction. | The Analyst 20060201 |
| Process model and economic analysis of itaconic acid production from dimethyl succinate and formaldehyde. | Bioresource technology 20060101 |
| Hexylitaconic acid: a new inhibitor of p53-HDM2 interaction isolated from a marine-derived fungus, Arthrinium sp. | Bioorganic & medicinal chemistry letters 20060101 |
| An investigation into the influence of hydrogel composition on swelling behavior and drug release from poly(acrylamide-co-itaconic acid) hydrogels in various media. | Drug delivery 20060101 |
| The release of bovine serum albumin from polyurethane based hydrophilic and hydrophobic disks and microbiological interactions. | Bio-medical materials and engineering 20060101 |
| Integration of metabolome data with metabolic networks reveals reporter reactions. | Molecular systems biology 20060101 |
| Synthesis and application of phosphinoferrocenylaminophosphine ligands for asymmetric catalysis. | The Journal of organic chemistry 20050304 |
| Swelling behavior and mechanical properties of poly(acrylamide-co-itaconic acid) hydrogels and their semi-IPNS with poly(ethylene glycol). | Journal of controlled release : official journal of the Controlled Release Society 20050103 |
| Swelling and paracetamol release studies of poly(acrylamide-co-itaconic acid) hydrogels. | Journal of controlled release : official journal of the Controlled Release Society 20050103 |
| The molecular reaction vessels for a transesterification process created by molecular imprinting technique. | Journal of molecular recognition : JMR 20050101 |
| Novel method for cell immobilization and its application for production of organic acid. | Letters in applied microbiology 20050101 |
| Organic acid toxicity, tolerance, and production in Escherichia coli biorefining applications. | Microbial cell factories 20050101 |
| A molecularly imprinted catalyst designed by a computational approach in catalysing a transesterification process. | Biosensors & bioelectronics 20041215 |
| Polycarboxylic acid nanoparticles for ophthalmic drug delivery: an ex vivo evaluation with human cornea. | Journal of microencapsulation 20041201 |
| Multi-maleimides bearing electron-donating chromophores: reversible fluorescence and aggregation behavior. | Journal of the American Chemical Society 20041006 |
| Synthesis of new monodentate spiro phosphoramidite ligand and its application in Rh-catalyzed asymmetric hydrogenation reactions. | Organic letters 20040930 |
| H(2) production and carbon utilization by Thermotoga neapolitana under anaerobic and microaerobic growth conditions. | Biotechnology letters 20040801 |
| Preparation of poly(N-isopropylacrylamide/itaconic acid) copolymeric hydrogels and their drug release behavior. | International journal of pharmaceutics 20040708 |
| Intracellular expression of Vitreoscilla hemoglobin in Aspergillus terreus to alleviate the effect of a short break in aeration during culture. | Biotechnology letters 20040701 |
| Monitoring of a heterogeneous reaction by acoustic emission. | The Analyst 20040501 |
| Itaconate reduces visceral fat by inhibiting fructose 2,6-bisphosphate synthesis in rat liver. | Nutrition (Burbank, Los Angeles County, Calif.) 20040101 |
| Ceriporic acid C, a hexadecenylitaconate produced by a lignin-degrading fungus, Ceriporiopsis subvermispora. | Chemistry and physics of lipids 20031201 |
| Specific interactions study in complexes of poly(mono-n-alkyl itaconates) with tertiary polyamides. | Applied spectroscopy 20030701 |
| Monitoring of itaconic acid hydrogenation in a trickle bed reactor using fiber-optic coupled near-infrared spectroscopy. | Applied spectroscopy 20030301 |
| Asymmetric hydrogenation of itaconic acid and enol acetate derivatives with the Rh-TangPhos catalyst. | Organic letters 20030123 |
| Concise synthesis of (+/-)-horsfiline and (+/-)-coerulescine by tandem cyclisation of iodoaryl alkenyl azides. | Organic & biomolecular chemistry 20030107 |
| A novel chiral ferrocenyl phosphine ligand from sugar: applications in Rh-catalyzed asymmetric hydrogenation reactions. | Organic letters 20021212 |
| Chemical synthesis, iron redox interactions and charge transfer complex formation of alkylitaconic acids from Ceriporiopsis subvermispora. | Chemistry and physics of lipids 20021201 |
| Inhibition of acetate and propionate assimilation by itaconate via propionyl-CoA carboxylase in isocitrate lyase-negative purple bacterium Rhodospirillum rubrum. | FEMS microbiology letters 20021029 |
| A selective lignin-degrading fungus, Ceriporiopsis subvermispora, produces alkylitaconates that inhibit the production of a cellulolytic active oxygen species, hydroxyl radical in the presence of iron and H(2)O(2). | Biochemical and biophysical research communications 20021004 |
| Enhanced production of itaconic acid from corn starch and market refuse fruits by genetically manipulated Aspergillus terreus SKR10. | Bioresource technology 20021001 |
| Pseudomonas grimontii sp. nov. | International journal of systematic and evolutionary microbiology 20020901 |
| Retention of alkali, alkaline earth and transition metals on an itaconic acid cation-exchange column. Eluent pH, ionic strength and temperature effects upon selectivity. | Journal of chromatography. A 20020726 |
| Vibrio trachuri Iwamoto et al. 1995 is a junior synonym of Vibrio harveyi (Johnson and Shunk 1936) Baumann et al. 1981. | International journal of systematic and evolutionary microbiology 20020501 |
| Purification and characterization of isocitrate lyase from the wood-destroying basidiomycete Fomitopsis palustris grown on glucose. | Archives of biochemistry and biophysics 20020315 |
| Identification of a novel series of alkylitaconic acids in wood cultures of Ceriporiopsis subvermispora by gas chromatography/mass spectrometry. | Rapid communications in mass spectrometry : RCM 20020101 |
| Purification and characterization of cis-aconitic acid decarboxylase from Aspergillus terreus TN484-M1. | Journal of bioscience and bioengineering 20020101 |
| Identification of the gene and characterization of the activity of the trans-aconitate methyltransferase from Saccharomyces cerevisiae. | Biochemistry 20011113 |
| Controlled release of antifungal drug terbinafine hydrochloride from poly(N-vinyl 2-pyrrolidone/itaconic acid) hydrogels. | International journal of pharmaceutics 20011009 |
| Aggressiveness of contemporary self-etching adhesives. Part II: etching effects on unground enamel. | Dental materials : official publication of the Academy of Dental Materials 20010901 |
| Biotechnological production of itaconic acid. | Applied microbiology and biotechnology 20010801 |
| Isotachophoretic separation behavior of rare-earth EDTA chelates and analysis of minor rare-earth elements in an iron ore by bidirectional isotachophoresis-particle-induced X-ray emission. | Journal of chromatography. A 20010615 |
| Thermoprecipitation of lysozyme from egg white using copolymers of N-isopropylacrylamide and acidic monomers. | Journal of biotechnology 20010504 |
| The effect of acid etching on vascular diameter of pulp-vessels in rat incisor (vitalmicroscopic study). | Operative dentistry 20010101 |
| The biochemistry of citric acid accumulation by Aspergillus niger. | Acta microbiologica et immunologica Hungarica 20010101 |
| Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro. | Annals of tropical medicine and parasitology 19961201 |
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