2-Methylcitric acid

Names

[ Name ]:
2-Methylcitric acid

[Synonym ]:
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

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]:

Research Areas >> Metabolic Disease

[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

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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%