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59464

Sigma-Aldrich

Trisodium 2-methylcitrate, racemic mixture of diastereomers

≥85% (mixture of diastereomers, NMR)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C7H7Na3O7
Numéro CAS:
117041-96-0
Poids moléculaire :
272.10
Numéro MDL:
MFCD16875437
Code UNSPSC :
12352107
ID de substance PubChem :
329758670
Nomenclature NACRES :
NA.25

Niveau de qualité

100

Pureté

≥85% (mixture of diastereomers, NMR)

Forme

solid

Impuretés

≤5% water

Chaîne SMILES 

[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

Clé InChI

HPLKAWNRQOHUKD-UHFFFAOYSA-K

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Application

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

Actions biochimiques/physiologiques

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.

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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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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