Skip to Content
Merck
All Photos(1)

Key Documents

More Documents

59464

Sigma-Aldrich

Trisodium 2-methylcitrate, racemic mixture of diastereomers

≥85% (mixture of diastereomers, NMR)

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C7H7Na3O7
CAS Number:
117041-96-0
Molecular Weight:
272.10
MDL number:
MFCD16875437
UNSPSC Code:
12352107
PubChem Substance ID:
329758670
NACRES:
NA.25

Assay

≥85% (mixture of diastereomers, NMR)

form

solid

impurities

≤5% water

SMILES string

[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

InChI key

HPLKAWNRQOHUKD-UHFFFAOYSA-K

Looking for similar products? Visit Product Comparison Guide

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service