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Merck
CN

59464

Trisodium 2-methylcitrate, racemic mixture of diastereomers

≥85% (mixture of diastereomers, NMR)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C7H7Na3O7
CAS Number:
117041-96-0
Molecular Weight:
272.10
NACRES:
NA.25
PubChem Substance ID:
329758670
UNSPSC Code:
12352107
MDL number:
MFCD16875437
Assay:
≥85% (mixture of diastereomers, NMR)
Form:
solid
Quality level:
100

Key Documents

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Product Name

Trisodium 2-methylcitrate, racemic mixture of diastereomers, ≥85% (mixture of diastereomers, NMR)

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

SMILES string

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

InChI key

HPLKAWNRQOHUKD-UHFFFAOYSA-K

assay

≥85% (mixture of diastereomers, NMR)

form

solid

impurities

≤5% water

Quality Level

100

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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

Biochem/physiol Actions

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCF5393
BCBW7168
BCBB6963V
BCBB6963

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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
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)
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
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
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