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16859

Sigma-Aldrich

D-α-Hydroxyglutaric acid disodium salt

≥98.0% (GC)

Synonym(s):

(R)-2-Hydroxypentanedioic acid disodium salt, Disodium (R)-2-hydroxyglutarate

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About This Item

Linear Formula:
C5H6O5Na2
CAS Number:
103404-90-6
Molecular Weight:
192.08
Beilstein/REAXYS Number:
5318041
MDL number:
MFCD00069573
UNSPSC Code:
12352106
PubChem Substance ID:
329751400
NACRES:
NA.25

Quality Level

100

assay

≥98.0% (GC)

form

powder or crystals

optical activity

[α]/D 8.5±1.5°, c = 1 in NaOH

impurities

≤6.0% water

storage temp.

2-8°C

SMILES string

[Na].O[C@H](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/t3-;;/m1../s1

InChI key

DZHFTEDSQFPDPP-HWYNEVGZSA-L

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Biochem/physiol Actions

Biomarker for inborn errors of metabolism and cancer

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Stefan Nowicki et al.
The FEBS journal, 282(15), 2796-2805 (2015-04-14)
Increased glucose metabolism in cancer cells is a phenomenon that has been known for over 90 years, allowing maximal cell growth through faster ATP production and redistribution of carbons towards nucleotide, protein and fatty acid synthesis. Recently, metabolites that can
Seth J Parker et al.
Pharmacology & therapeutics, 152, 54-62 (2015-05-10)
Specific point mutations in isocitrate dehydrogenase 1 and 2 (IDH1 and IDH2) occur in a variety of cancers, including acute myeloid leukemia (AML), low-grade gliomas, and chondrosarcomas. These mutations inactivate wild-type enzymatic activity and convey neomorphic function to produce d-2-hydroxyglutarate
M S Rashed et al.
Biomedical chromatography : BMC, 14(5), 317-320 (2000-08-29)
D-2-Hydroxyglutaric aciduria and L-2-hydroxyglutaric aciduria are two distinct inherited metabolic diseases. The accurate diagnosis of the exact disorder relies on the determination of the configuration of the enantiomers, either D-2-hydroxyglutaric acid or L-2-hydroxyglutaric acid excreted in excess in urine of
Martijn Kranendijk et al.
Journal of inherited metabolic disease, 35(4), 571-587 (2012-03-07)
The organic acidurias D: -2-hydroxyglutaric aciduria (D-2-HGA), L-2-hydroxyglutaric aciduria (L-2-HGA), and combined D,L-2-hydroxyglutaric aciduria (D,L-2-HGA) cause neurological impairment at young age. Accumulation of D-2-hydroxyglutarate (D-2-HG) and/or L-2-hydroxyglutarate (L-2-HG) in body fluids are the biochemical hallmarks of these disorders. The current
Andrew J Worth et al.
Chemical research in toxicology, 28(5), 948-954 (2015-03-25)
The α-ketoglutarate metabolite, 2-hydroxyglutarate (2-HG), has emerged as an important mediator in a subset of cancers and rare inherited inborn errors of metabolism. Because of potential enantiospecific metabolism, chiral analysis is essential for determining the biochemical impacts of altered 2-HG
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