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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:
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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Stereochemical studies on porphyrin a: assignment of the absolute configuration of a model porphyrin by degradation.
Battersby, A.R., et al.
Journal of the Chemical Society. Perkin Transactions 1, 9, 1565-1580 (1986)
Stereospecific ketonization of 2-hydroxymuconate by 4-oxalocrotonate tautomerase and 5-(carboxymethyl)-2-hydroxymuconate isomerase.
Whitman, C.P., et al.
Journal of the American Chemical Society, 114, 10104-10110 (1992)
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
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
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
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