D-α-Hydroxyglutaric acid (Synonyms: (R)-2-Hydroxyglutarate; (R)-2-Hydroxyglutaric acid; (R)-2-Hydroxypentanedioic acid)

Cat. No.: HY-113038: FAQs
Data Sheet Handling Instructions

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D-α-Hydroxyglutaric acid ((R)-2-Hydroxyglutarate) is the principal metabolite accumulating in neurometabolic disease D-2-hydroxyglutaric aciduria. D-α-Hydroxyglutaric acid is a weak competitive antagonist of α-ketoglutarate (α-KG) and inhibits multiple α-KG-dependent dioxygenases with a K_i of 10.87 mM. D-α-Hydroxyglutaric acid increases reactive oxygen species (ROS) production. D-α-Hydroxyglutaric acid binds and inhibits ATP synthase and inhibits mTOR signaling.

The free form of the compound is prone to instability, it is advisable to consider the stable salt form (D-α-Hydroxyglutaric acid disodium) that retains the same biological activity.

For research use only. We do not sell to patients.

D-α-Hydroxyglutaric acid Chemical Structure

CAS No. : 13095-47-1

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Other In-stock Forms of D-α-Hydroxyglutaric acid:

D-α-Hydroxyglutaric acid disodium α-Hydroxyglutaric acid

Other Forms of D-α-Hydroxyglutaric acid:

D-α-Hydroxyglutaric acid disodium In-stock
α-Hydroxyglutaric acid In-stock

2 Publications Citing Use of MCE D-α-Hydroxyglutaric acid

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Biological Activity
Purity & Documentation
References
Customer Review

Description

IC₅₀ & Target

Microbial Metabolite

Human Endogenous Metabolite

In Vitro

D-α-Hydroxyglutaric acid ((R)-2-hydroxyglutarate) accumulates in human cancers carrying neomorphic mutations in the isocitrate dehydrogenase (IDH) 1 and 2 genes^[1]^[2].
A partial inhibition of KDM7A toward both H3K9me2 and H3K27me2 peptides is observed in the presence of 50 mM D-2-HG and 100 μM α-ketoglutarate (α-KG). Addition of 300 μM α-KG is capable of reversing the inhibition of Caenorhabditis elegans KDM7A (CeKDM7A) by 50 mM D-2-HG, indicating that D-2-HG is a weak competitive inhibitor against α-KG toward the CeKDM7A demethylase^[1].
D-α-Hydroxyglutaric acid is a weak inhibitor of TET hydroxylases. In the presence of 0.1 mM of α-KG, addition of 10 mM D-α-Hydroxyglutaric acid results in a partial (33%) inhibition of TET2 and addition of 50 mM D-α-Hydroxyglutaric acid results in more inhibition (83%) of TET2. D-α-Hydroxyglutaric acid exhibits a less pronounced inhibitory effect toward TET1^[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

D-α-Hydroxyglutaric acid strongly inhibits glucose utilization, CO₂ production and the respiratory chain in rat cerebral cortex and human skeletal muscle, as well as in submitochondrial particles from bovine heart, suggesting an impairment of the aerobic metabolism^[5].
D-α-Hydroxyglutaric acid has also been proposed as an endogenous excitotoxic organic acid because it significantly decreased cell viability in neuronal cultures from chick embryo telencephalons and from neonatal rat hippocampus through stimulation of specific NMDA glutamate receptors^[5].
D-α-Hydroxyglutaric acid (0.01-1 mM) significantly increases chemiluminescence and thiobarbituric acid-reactive substances (TBA-RS) and decreased total antioxidant reactivity (TAR) values in the cortical supernatants in 30-day-old-rats^[5].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Molecular Weight

148.11

Formula

C₅H₈O₅

CAS No.

13095-47-1

SMILES

O=C(O)[C@H](O)CCC(O)=O

Structure Classification

Ketones, Aldehydes, Acids

Initial Source

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Room temperature in continental US; may vary elsewhere.

Storage

Please store the product under the recommended conditions in the Certificate of Analysis.

Solvent & Solubility

In Vitro:

H₂O : 200 mg/mL (1350.35 mM; Need ultrasonic)

Preparing
Stock Solutions

Concentration Solvent Mass	1 mg	5 mg	10 mg

1 mM	6.7517 mL	33.7587 mL	67.5174 mL
5 mM	1.3503 mL	6.7517 mL	13.5035 mL
10 mM	0.6752 mL	3.3759 mL	6.7517 mL

View the Complete Stock Solution Preparation Table

* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.

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Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Concentration _(start) × Volume _(start) = Concentration _(final) × Volume _(final)

This equation is commonly abbreviated as: C₁V₁ = C₂V₂

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Calculation results:

Working solution concentration: mg/mL

This product has good water solubility, please refer to the measured solubility data in water/PBS/Saline for details.

The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only.If necessary, please contact MedChemExpress (MCE).

Purity & Documentation

Handling Instructions (2659 KB)

References

[1]. Xu W, et al. Oncometabolite 2-hydroxyglutarate is a competitive inhibitor of α-ketoglutarate-dependent dioxygenases. Cancer Cell. 2011 Jan 18;19(1):17-30. [Content Brief]

[2]. Fu X, et al. 2-Hydroxyglutarate Inhibits ATP Synthase and mTOR Signaling. Cell Metab. 2015 Sep 1;22(3):508-15. [Content Brief]

[3]. Martijn Kranendijk, et al. Progress in understanding 2-hydroxyglutaric acidurias. J Inherit Metab Dis. 2012 Jul;35(4):571-87. [Content Brief]

[4]. Martin Böttcher, et al. D-2-hydroxyglutarate interferes with HIF-1α stability skewing T-cell metabolism towards oxidative phosphorylation and impairing Th17 polarization. Oncoimmunology. 2018 Mar 26;7(7):e1445454. [Content Brief]

[5]. Alexandra Latini , et al. D-2-hydroxyglutaric acid induces oxidative stress in cerebral cortex of young rats. Eur J Neurosci. 2003 May;17(10):2017-22. [Content Brief]

Complete Stock Solution Preparation Table

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg

H₂O	1 mM	6.7517 mL	33.7587 mL	67.5174 mL	168.7935 mL
	5 mM	1.3503 mL	6.7517 mL	13.5035 mL	33.7587 mL
	10 mM	0.6752 mL	3.3759 mL	6.7517 mL	16.8793 mL
	15 mM	0.4501 mL	2.2506 mL	4.5012 mL	11.2529 mL
	20 mM	0.3376 mL	1.6879 mL	3.3759 mL	8.4397 mL
	25 mM	0.2701 mL	1.3503 mL	2.7007 mL	6.7517 mL
	30 mM	0.2251 mL	1.1253 mL	2.2506 mL	5.6264 mL
	40 mM	0.1688 mL	0.8440 mL	1.6879 mL	4.2198 mL
	50 mM	0.1350 mL	0.6752 mL	1.3503 mL	3.3759 mL
	60 mM	0.1125 mL	0.5626 mL	1.1253 mL	2.8132 mL
	80 mM	0.0844 mL	0.4220 mL	0.8440 mL	2.1099 mL
	100 mM	0.0675 mL	0.3376 mL	0.6752 mL	1.6879 mL

* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.

D-α-Hydroxyglutaric acid Related Classifications

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Do most proteins show cross-species activity?
Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

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