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59464

Sigma-Aldrich

Trisodium 2-methylcitrate, racemic mixture of diastereomers

≥85% (mixture of diastereomers, NMR)

Sinonimo/i:

Trisodium 3-carboxy-3-hydroxy-2-methyl-pentanedioate

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About This Item

Formula empirica (notazione di Hill):
C7H7Na3O7
Numero CAS:
117041-96-0
Peso molecolare:
272.10
Numero MDL:
MFCD16875437
Codice UNSPSC:
12352107
ID PubChem:
329758670
NACRES:
NA.25

Livello qualitativo

100

Saggio

≥85% (mixture of diastereomers, NMR)

Forma fisica

solid

Impurezze

≤5% water

Stringa SMILE

[Na+].[Na+].[Na+].CC(C([O-])=O)C(O)(CC([O-])=O)C([O-])=O

InChI

1S/C7H10O7.3Na/c1-3(5(10)11)7(14,6(12)13)2-4(8)9;;;/h3,14H,2H2,1H3,(H,8,9)(H,10,11)(H,12,13);;;/q;3*+1/p-3
HPLKAWNRQOHUKD-UHFFFAOYSA-K

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Applicazioni

2-Methylcitrate is a component of the 2-methylcitric acid (2-MCA) cycle that utilizes propionate as a source of carbon and energy in bacteria. Trisodium 2-methylcitrate may be used to study this pathway

Azioni biochim/fisiol

MCA is a diagnostic marker metabolite which cumulates in body fluids of patients suffering from the following inherited metabolic diseases: propionic acidemia (PA), methylmalonic aciduris (MMA), holocarboxylase synthetase deficiency (HCSD). There MCA occurs as a mixture of (2S,3S)- and (2R,3S)-stereoisomers.

Confezionamento

Bottomless glass bottle. Contents are inside inserted fused cone.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Certificati d'analisi (COA)

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Characterization of the 1H and 13C NMR spectra of methylcitric acid.
Krawczyk, H. and Martyniuk, T.
Spectrochimica Acta Part A: Molecular Spectroscopy, 67, 298-305 (2007)
S Cheema-Dhadli et al.
Pediatric research, 9(12), 905-908 (1975-12-01)
2-Methylcitrate was tested in vitro on enzymes which interact with citrate and isocitrate. It was found to inhibit citrate synthase, aconitase, the NAD+- and NADP+-linked isocitrate dehydrogenase. This inhibition was competitive in nature except in the case of aconitase, and
Sagar Chittori et al.
Journal of structural biology, 174(1), 58-68 (2010-10-26)
2-Methylcitric acid (2-MCA) cycle is one of the well studied pathways for the utilization of propionate as a source of carbon and energy in bacteria such as Salmonella typhimurium and Escherichia coli. 2-Methylcitrate synthase (2-MCS) catalyzes the conversion of oxaloacetate
Sergio Palacios et al.
Journal of bacteriology, 185(9), 2802-2810 (2003-04-18)
The studies reported here identify propionyl coenzyme A (propionyl-CoA) as the common intermediate in the 1,2-propanediol and propionate catabolic pathways of Salmonella enterica serovar Typhimurium LT2. Growth on 1,2-propanediol as a carbon and energy source led to the formation and
Sagar Chittori et al.
Acta crystallographica. Section F, Structural biology and crystallization communications, 66(Pt 4), 467-470 (2010-04-13)
Analysis of the genomic sequences of Escherichia coli and Salmonella typhimurium has revealed the presence of several homologues of the well studied citrate synthase (CS). One of these homologues has been shown to code for 2-methylcitrate synthase (2-MCS) activity. 2-MCS
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