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90790 Sigma-Aldrich

L-α-Hydroxyglutaric acid disodium salt

≥98.0% (GC)

Synonym: (S)-2-Hydroxypentanedioic acid disodium salt, Disodium (S)-2-hydroxyglutarate

  • CAS Number 63512-50-5

  • Linear Formula C5H6O5Na2

  • Molecular Weight 192.08

  •  Beilstein/REAXYS Number 5318042

  •  MDL number MFCD00021700

  •  PubChem Substance ID 329769949

  •  NACRES NA.32

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Properties

Related Categories Biochemicals and Reagents, Cancer Metabolism, Cancer Research, Cell Biology, Dicarboxylic Acids,
Quality Level   100
assay   ≥98.0% (GC)
form   powder or crystals
optical activity   [α]/D -8.5±1.5°, c = 1 in 0.1 M NaOH
impurities   ≤6.0% water
relevant disease(s)   cancer
storage temp.   2-8°C
SMILES string   [O-]C(CC[C@@H](C([O-])=O)O)=O.[Na+].[Na+]
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-;;/m0../s1
InChI key   DZHFTEDSQFPDPP-QTNFYWBSSA-L

Description

General description

Glutamic acid is metabolized to α-Hydroxyglutaric acid in an NAD-dependent manner by cell-free extracts of Peptococcus aerogenes. It is formed as an intermediate during glyoxylic acid metabolism in bacteria.

Application

L-α-Hydroxyglutaric acid disodium salt is suitable for use in collection buffer for increased recovery of hypoxia-inducible factor-1 α (HIF-1α), a marker of hypoxia in human tumors. It is also suitable for the radiolabeled 5mC-5hmC conversion assay to study the effect of 2-HG on the TET family of methyl hydroxylases.

Biochem/physiol Actions

L-alpha-Hydroxyglutaric acid accumulates as a result of a rare defect in L-2-HG dehydogenase, leading to the metabolic disorder L-2-hydroxyglutaric aciduria (L-2HGA). L-2HGA is associated with neuronal defects, leukodystrophy and linked to an increased risk of brain tumors.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

Please Enter a Lot Number

Frequently Asked Questions

Which document(s) contains shelf-life or expiration date information for a given product?
If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.
How do I get lot-specific information or a Certificate of Analysis?
The lot specific COA document can be found by entering the lot number above under the "Documents" section.
How do I find price and availability?
There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote. USA customers: 1-800-325-3010 or view local office numbers.
What is the Department of Transportation shipping information for this product?
Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
Is Product 90790, L-α-Hydroxyglutaric acid disodium salt cell membranepermeable?
We have not tested the cell membranepermeability of Product 90790, L-α-Hydroxyglutaric acid disodium salt. A helpful reference discussing the use of L-α-Hydroxyglutaric acid disodium salt to treat zebrafish is listed below.Parng, C.et al., Neurotoxicology and Teratology, 28, 509-516 , (2006).
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Protocols & Articles

Articles

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

Chiral 2-hydroxyglutarates (2-OHG) are important molecular signatures of their specific biochemical pathways and inborn errors of metabolism, for both healthy and diseased biological cells. For examp...
Roland Wöhlgemuth, Rudolf Köhling, Hugh Cramer
Reporter Volume 31.3
Keywords: Asymmetric synthesis, Cancer, Citric Acid Cycle, High performance liquid chromatography, Liquid chromatography mass spectrometry, Mass spectrometry, Metabolism, Metabolites, Phase transitions, Reductions, Separation

Genotype-Phenotype-Relationships in Inborn Errors of Metabolism

More than a century has passed since Archibald Garrod connected the excretion of homogentisic acid in normal and alkaptonuric members of families with an alternative course of metabolism and entitled...
Keywords: Genetic, Metabolism, Metabolites

LC/MS/MS Analysis of DL-d-Hydroxyglutaric Acid Enantiomers on Astec® CHIROBIOTIC® R

From our library of Articles, Sigma-Aldrich presents LC/MS/MS Analysis of DL-d-Hydroxyglutaric Acid Enantiomers on Astec® CHIROBIOTIC® R
Keywords: Asymmetric synthesis, Chromatography, Clinical, Forensic, High performance liquid chromatography, Liquid chromatography mass spectrometry, Mass spectrometry, Metabolism, Metabolites, Phase transitions, Separation

LCMS Separation and Identification of 2-Hydroxyglutarates

Sigma-Aldrich has recently developed an application for the separation and identification of S-2-hydroxyglutaric acids and R-2-hydroxyglutaric acids by chiral LC-MS, using a CHIROBIOTIC® R Column (co...
Keywords: AGE, Cancer, High performance liquid chromatography, Liquid chromatography mass spectrometry, Mass spectrometry, Metabolism, Reductions, Separation, Tools

OAMLS Online Plate Map

OAMLS compounds are conveniently provided at 5µg per well, enough for multiple injections. These are high purity (>95%) compounds supplied in an economical, ready to use format. Compounds are arrange...
Keywords: Metabolites

Peer-Reviewed Papers
15

References

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