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94577

Sigma-Aldrich

DL-α-Hydroxyglutaric acid disodium salt

≥95.0% (GC)

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Synonym(s):
(RS)-2-Hydroxypentanedioic acid disodium salt, Disodium 2-hydroxyglutarate
Linear Formula:
C5H6O5Na2
CAS Number:
40951-21-1
Molecular Weight:
192.08
MDL number:
MFCD03939807
UNSPSC Code:
12352204
PubChem Substance ID:
329770365
NACRES:
NA.28

Quality Level

100

Assay

≥95.0% (GC)

form

powder or crystals

impurities

≤6.0% water

storage temp.

2-8°C
2-8°C

SMILES string

[Na+].[Na+].OC(CCC([O-])=O)C([O-])=O

InChI

1S/C5H8O5.2Na/c6-3(5(9)10)1-2-4(7)8;;/h3,6H,1-2H2,(H,7,8)(H,9,10);;/q;2*+1/p-2

InChI key

DZHFTEDSQFPDPP-UHFFFAOYSA-L

Biochem/physiol Actions

D-(or R-) enantiomer of α-hydroxyglutaric acid is a cancer related biomarker of diagnostic value, whereas the L-(or S-) enantiomer of α-hydroxyglutaric acid is a biomarker for certain neurometabolic, inherited disorder diseases. It has no known physiological function in eukaryotes. It is toxic to the brain and increases the susceptibility to develop brain tumors.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

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’.

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Cancer-associated IDH mutations: biomarker and therapeutic opportunities
K E Yen
Oncogene (2010)
Cancer-associated IDH1 mutations produce 2-hydroxyglutarate
Lenny Dang
Nature (2009)
Fang Wang et al.
Science (New York, N.Y.), 340(6132), 622-626 (2013-04-06)
A number of human cancers harbor somatic point mutations in the genes encoding isocitrate dehydrogenases 1 and 2 (IDH1 and IDH2). These mutations alter residues in the enzyme active sites and confer a gain-of-function in cancer cells, resulting in the
Cancer: A metabolic metamorphosis.
Abigail S Krall et al.
Nature, 496(7443), 38-40 (2013-04-05)
Jelena Lazovic et al.
Neuro-oncology, 14(12), 1465-1472 (2012-10-24)
The arginine 132 (R132) mutation of isocitrate dehydrogenase -1 (IDH1(R132)) results in production of 2-hydroxyglutarate (2-HG) and is associated with a better prognosis compared with wild-type (WT) in glioma patients. The majority of lower-grade gliomas express IDH1(R132), whereas this mutation
View All Related Papers

Protocols

Chiral LC-MS/MS of D- and L-2-Hydroxyglutaric Acid Biomarkers

We describe here a rapid and sensitive method to separate and measure D-2-OHG and L-2-OHG enantiomers using high-resolution mass spectrometry (HRMS) detection.

Chromatograms

application for HPLCapplication for HPLC

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