(±)-2-Hydroxyglutaric acid

Names

[ Name ]:
(±)-2-Hydroxyglutaric acid

[Synonym ]:
hydroxyglutaric acid
Pentanedioic acid, 2-hydroxy-
2-Hydroxypentanedioic acid
2-hydroxyglutaric acid
DL-2-Hydroxyglutaric
(RS)-2-Hydroxypentanedioic acid disodium salt Disodium 2-hydroxyglutarate
2-Hydroxy-pentanedioic acid

Biological Activity

[Description]:

α-Hydroxyglutaric acid (2-Hydroxyglutarate) disodium is an α-hydroxy acid form of glutaric acid. α-Hydroxyglutaric acid disodium is a competitive inhibitor of multiple α-ketoglutarate-dependent dioxygenases, including histone demethylases and the TET family of 5-methlycytosine (5mC) hydroxylases[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Epigenetics >> Histone Demethylase

[Target]

Microbial Metabolite

Human Endogenous Metabolite

[In Vitro]

Isocitrate Dehydrogenase 1 (IDH1) and IDH2 mutations occur frequently in gliomas and acute myeloid leukemia, leading to simultaneous loss and gain of activities in the production of α-ketoglutarate (α-KG) and α-Hydroxyglutaric acid (2-Hydroxyglutarate) disodium, respectively[1]. α-Hydroxyglutaric acid (2-Hydroxyglutarate) disodium inhibits the activity of multiple histone demethylases. α-Hydroxyglutaric acid occupies the same space as α-KG does in the active site of histone demethylases. α-Hydroxyglutaric acid (2-Hydroxyglutarate) disodium inhibits the activity of TET 5-methylcytosine hydroxylases[1]. Treatment of U-87MG cells with α-Hydroxyglutaric acid (2-Hydroxyglutarate; 10-50 mM) disodium increases HIF-1α and decreases endostatin[1].

[References]

[1]. Wei Xu, et al. Oncometabolite 2-hydroxyglutarate is a competitive inhibitor of α-ketoglutarate-dependent dioxygenases. Cancer Cell. 2011 Jan 18;19(1):17-30.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
394.2±27.0 °C at 760 mmHg

[ Melting Point ]:
>290ºC (dec.)

[ Molecular Formula ]:
C₅H₈O₅

[ Molecular Weight ]:
148.114

[ Flash Point ]:
206.4±20.2 °C

[ Exact Mass ]:
148.037170

[ PSA ]:
94.83000

[ LogP ]:
-1.45

[ Vapour Pressure ]:
0.0±2.1 mmHg at 25°C

[ Index of Refraction ]:
1.520

MSDS

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Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: MA3751000

CHEMICAL NAME :: Glutaric acid, 2-hydroxy-, disodium salt, L-alpha-

CAS REGISTRY NUMBER :: 40951-21-1

LAST UPDATED :: 199012

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C5-H6-O5.Na2

MOLECULAR WEIGHT :: 192.09

WISWESSER LINE NOTATION :: OVYQ2VO &-NA- 2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 4500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: RPTOAN Russian Pharmacology and Toxicology (English Translation). Translation of FATOAO. (Euromed Pub., 33, Woodlands Rd., Surbiton, Surrey, UK) V.30- 1967- Volume(issue)/page/year: 36,61,1973

Synthetic Route

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Precursor & DownStream

Precursor

DownStream

Related Compounds

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