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Merck

90790

L-α-Hydroxyglutaric acid disodium salt

≥98.0% (GC)

Synonym(s):

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

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MXP 2,126.00

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MXP 7,399.00

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About This Item

Linear Formula:
C5H6O5Na2
CAS Number:
Molecular Weight:
192.08
UNSPSC Code:
12352106
NACRES:
NA.32
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
5318042

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Product Name

L-α-Hydroxyglutaric acid disodium salt, ≥98.0% (GC)

SMILES string

[O-]C(CC[C@@H](C([O-])=O)O)=O.[Na+].[Na+]

InChI key

DZHFTEDSQFPDPP-QTNFYWBSSA-L

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

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

Quality Level

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This Item
H83789457716859
assay

≥98.0% (GC)

assay

≥95% (GC)

assay

≥95.0% (GC)

assay

≥98.0% (GC)

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

100

form

powder or crystals

form

powder

form

powder or crystals

form

powder or crystals

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

optical activity

[α]/D -8.5±1.5°, c = 1 in 0.1 M NaOH

optical activity

-

optical activity

-

optical activity

[α]/D 8.5±1.5°, c = 1 in NaOH

impurities

≤6.0% water

impurities

-

impurities

≤6.0% water

impurities

≤6.0% water

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.[1] 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.[2]

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.

General description

Glutamic acid is metabolized to α-Hydroxyglutaric acid in an NAD-dependent manner by cell-free extracts of Peptococcus aerogenes.[3] It is formed as an intermediate during glyoxylic acid metabolism in bacteria.[4][5]

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Hugh Colvin et al.
Scientific reports, 6, 36289-36289 (2016-11-09)
Deranged metabolism is a hallmark of cancer, playing a significant role in driving the disease process. One such example is the induction of carcinogenesis by the oncometabolite D-2 hydroxyglutarate (D-2HG), which is produced by the mutated enzyme isocitrate dehydrogenase (IDH)
Rapid separation of some common intermediates of microbial metabolism by thin-layer chromatography.
A S Bleiweis et al.
Analytical biochemistry, 20(2), 335-338 (1967-08-01)
A S Bleiweis et al.
Journal of bacteriology, 94(5), 1560-1564 (1967-11-01)
Aspergillus glaucus, cultured on sodium propionate-mineral salts medium, incorporates (14)C-glyoxylate into labeled alpha-hydroxyglutaric acid within 30 sec. Mycelial extracts retain this biosynthetic capacity, which is destroyed by heating. Propionyl-2-(14)C-coenzyme A also in incorporated into labeled alpha-hydroxyglutaric acid by these mycelial
Peppi Koivunen et al.
Nature, 483(7390), 484-488 (2012-02-22)
The identification of succinate dehydrogenase (SDH), fumarate hydratase (FH) and isocitrate dehydrogenase (IDH) mutations in human cancers has rekindled the idea that altered cellular metabolism can transform cells. Inactivating SDH and FH mutations cause the accumulation of succinate and fumarate
The production of alpha-hydroxyglutaric acid from glutamic acid by cell-free preparations of Peptococcus aerogenes.
W M Johnson et al.
Canadian journal of biochemistry, 47(12), 1103-1107 (1969-12-01)

Protocols

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.

Questions

1–2 of 2 Questions  
  1. Is Product 90790, L-α-Hydroxyglutaric acid disodium salt cell membrane permeable?

    1 answer
    1. We have not tested the cell membrane permeability 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).

      Helpful?

  2. What is the Department of Transportation shipping information for this product?

    1 answer
    1. 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.

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