2-methylenesuccinic acid - CAS 97-65-4
Catalog number: 97-65-4
Category: Intermediates
Molecular Formula:
C5H6O4
Molecular Weight:
130.10
COA:
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Purity:
98%
Appearance:
white to light beige crystalline powder
Synonyms:
methylene-butanedioicaci; methylene-succinicaci; Succinic acid, methylene-; METHYLENESUCCINIC ACID; ITACONIC ACID; 3-CARBOXY-3-BUTENOIC ACID; 2-PROPENE-1,2-DICARBOXYLIC ACID; PROPYLENEDICARBOXYLIC ACID
Storage:
Keep container closed when not in use. Store in a cool, dry, well-ventilated area away from incompatible substances.
MSDS:
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Quantity:
Data not available, please inquire.
Boiling Point:
381.4ºC at 760 mmHg
Melting Point:
166-167ºC
Density:
1.573
Physical Description:
Itaconic acid 99+% (250g)
1.Stereocomplementary bioreduction of alpha,beta-unsaturated dicarboxylic acids and dimethyl esters using enoate reductases: enzyme- and substrate-based stereocontrol.
Stueckler C1, Hall M, Ehammer H, Pointner E, Kroutil W, Macheroux P, Faber K. Org Lett. 2007 Dec 20;9(26):5409-11. Epub 2007 Nov 22.
Asymmetric bioreduction of alpha,beta-unsaturated dicarboxylic acids, such as 2-methylmaleic/fumaric and 2-methylenesuccinic acid, as well as the corresponding dimethyl esters, using three cloned enoate reductases furnished 2-methylsuccinic acid or dimethyl 2-methylsuccinate, respectively. Opposite stereoisomeric products were obtained in up to >99% ee either by choice of the enzyme or by using E/Z-configurated substrates. Cofactor-recycling systems (NADH/FDH/formate, NADH/GDH/glucose or NADPH/G6PDH/glucose-6-phosphate) only worked in presence of a divalent metal ion, such as Ca2+, Mg2+, or Zn2+.
2.Anaerobic cometabolic transformation of polycyclic and heterocyclic aromatic hydrocarbons: evidence from laboratory and field studies.
Safinowski M1, Griebler C, Meckenstock RU. Environ Sci Technol. 2006 Jul 1;40(13):4165-73.
The sulfate-reducing enrichment culture N47 can grow on naphthalene or 2-methylnaphthalene as the sole carbon and energy source. Here we show that the culture can furthermore cometabolicallytransform a variety of polycyclic and heteroaromatic compounds with naphthalene or methylnaphthalene as the auxiliary substrate. Most of the cosubstrates were converted to the corresponding carboxylic acids, frequently to several isomers. The mass spectra of specific metabolites that were extracted from supernatants of cultures containing the cosubstrates benzothiophene, benzofuran, and 1-methylnaphthalene resembled known intermediates of the anaerobic naphthalene and 2-methylnaphthalene degradation pathways (i.e., naphthyl-2-methylsuccinic acid and naphthyl-2-methylenesuccinic acid). This indicates that some of the tested compounds were first methylated and then transformed to the corresponding methylsuccinic acids by a fumarate addition to the methyl group.
3.Identification and quantification of polar naphthalene derivatives in contaminated groundwater of a former gas plant site by liquid chromatography-electrospray ionization tandem mass spectrometry.
Ohlenbusch G1, Zwiener C, Meckenstock RU, Frimmel FH. J Chromatogr A. 2002 Aug 23;967(2):201-7.
A liquid chromatography (LC) method followed by electrospray ionization (ESI) and tandem mass spectrometry (MS-MS) was developed for the quantification of acidic naphthalene derivatives in the concentration range 0.1 to 100 microg/l without excessive sample preparation. For optimal sensitivity the LC-MS-MS measurements were performed recording mass fragmentation by collision induced dissociation in the multiple reaction mode. The collision energy was optimized for every analyte. The matrix effects of the sample were investigated by spiking standards of 1-naphthoic acid with humic acid (HA) and with calcium chloride. While HA decreased the signal intensity an increase was observed in the presence of calcium chloride. For the investigated groundwater samples of a tar oil contaminated site a complete separation of the analytes from the sample matrix by reversed-phase separation could be obtained. The absence of matrix effects on quantification results was confirmed by comparison of results based on external calibration with those based on standard addition of the analytes to a groundwater sample.
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CAS 97-65-4 2-methylenesuccinic acid

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