2-Methylcitric acid

Modify Date: 2024-01-04 11:30:13

2-Methylcitric acid Structure
2-Methylcitric acid structure
Common Name 2-Methylcitric acid
CAS Number 6061-96-7 Molecular Weight 206.15000
Density 1.178g/cm3 Boiling Point 464.4ºC at 760 mmHg
Molecular Formula C7H10O7 Melting Point 79°C (lit.)
MSDS N/A Flash Point 234.7ºC

 Use of 2-Methylcitric acid


2-Methylcitric acid (Methylcitric acid) is an endogenous metabolite in the 2-methylcitric acid cycle. 2-Methylcitric acid accumulates in methylmalonic and propionic acidemias and acts as a marker metabolite. 2-Methylcitric acid markedly inhibits ADP-stimulated and uncoupled respiration in mitochondria supported by glutamate[1].

 Names

Name 2-methylcitric acid
Synonym More Synonyms

 2-Methylcitric acid Biological Activity

Description 2-Methylcitric acid (Methylcitric acid) is an endogenous metabolite in the 2-methylcitric acid cycle. 2-Methylcitric acid accumulates in methylmalonic and propionic acidemias and acts as a marker metabolite. 2-Methylcitric acid markedly inhibits ADP-stimulated and uncoupled respiration in mitochondria supported by glutamate[1].
Related Catalog
Target

Human Endogenous Metabolite

In Vitro 2-Methylcitric acid (Methylcitric acid) impairs glutamate metabolism and induces permeability transition in brain mitochondria. 2-Methylcitric acid inhibits glutamate dehydrogenase (GDH) activity at concentrations as low as 0.5 mM[1]. 2-Methylcitric acid (1-3 mM; 150 seconds) provokes a significant decrease in mitochondrial membrane potential and induced swelling in Ca2+-loaded mitochondria supported by different substrates[1]. 2-Methylcitric acid behaves as a potent inhibitor of glutamate oxidation by inhibiting glutamate dehydrogenase activity and as a permeability transition inducer, disturbing mitochondrial energy homeostasis. 2-Methylcitric acid does not significantly impair mitochondrial glutamate transport. 2-Methylcitric acid does not significantly impair glutamate mitochondrial transport in liver mitochondria[1].
References

[1]. Palacios S, et al. Propionyl Coenzyme A Is a Common Intermediate in the 1,2-Propanediol and Propionate Catabolic Pathways Needed for Expression of the prpBCDE Operon during Growth of Salmonella enterica on 1,2-Propanediol. J Bacteriol. 2003 May;185(9):2802-10.

 Chemical & Physical Properties

Density 1.178g/cm3
Boiling Point 464.4ºC at 760 mmHg
Melting Point 79°C (lit.)
Molecular Formula C7H10O7
Molecular Weight 206.15000
Flash Point 234.7ºC
Exact Mass 206.04300
PSA 132.13000
Index of Refraction 1.586

 Safety Information

HS Code 2918199090

 Synthetic Route

~%

2-Methylcitric acid Structure

2-Methylcitric acid

CAS#:6061-96-7

Literature: Habicht; Schneeberger Helvetica Chimica Acta, 1956 , vol. 39, p. 1316,1318

 Precursor & DownStream

Precursor  1

DownStream  0

 Customs

HS Code 2918199090
Summary 2918199090 other carboxylic acids with alcohol function but without other oxygen function, their anhydrides, halides, peroxides, peroxyacids and their derivatives。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%

 Synonyms

2-hydroxy-butane-1,2,3-tricarboxylic acid
1,2,3-Butanetricarboxylic acid,2-hydroxy
2-Hydroxy-butan-1,2,3-tricarbonsaeure
2-hydroxybutane-1,2,3-tricarboxylate
2-methylcitrate
2-hydroxy-1,2,3-butantricarbons
Methylcitronensaeure
2-hydroxybutane-1,2,3-tricarboxylic acid
2-hydroxy-1,2,3-butanetricarboxylic acid
2-Methylcitric acid