D-α-Hydroxyglutaric acid
Based on 4 publication(s) in Google Scholar
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 Ki 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.
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- Pureté: 98.0%
- CAS No.: 13095-47-1
- Formule: C5H8O5
- Masse moléculaire:148.11
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Stockage:Pure form -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month
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D-α-Hydroxyglutaric acid disodium
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Publications Citing Use of MedChemExpress (MCE) D-α-Hydroxyglutaric acid
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Activité biologique
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Human Endogenous Metabolite |
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.
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.
Chemical Information
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CAS No. 13095-47-1
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Appearance Solid-Liquid Mixture
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Masse moléculaire 148.11
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Formule C5H8O5
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Color Colorless to off-white
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SMILES
O=C(O)[C@H](O)CCC(O)=O
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Synonyms
(R)-2-Hydroxyglutarate; (R)-2-Hydroxyglutaric acid; (R)-2-Hydroxypentanedioic acid
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Structure Classification
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Livraison
Room temperature in continental US; may vary elsewhere.
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Stockage
Pure form -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Publications (4)
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Journal Impact Factor
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Most Recent
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Nat Commun
TRIM37-PARP1-TET1 axis maintains stemness and prevents osteoporosis by inhibiting DNMT1 alternative splicing via 5hmC regulation. [Abstract]2025 Dec 16;16(1):11420. PMID: 41402268
D-α-Hydroxyglutaric acid purchased from MedChemExpress. Usage Cited in: Nat Commun. 2025 Dec 16;16(1):11420. [Abstract]
Early MSCs were treated with D-α-Hydroxyglutaric acid disodium (2-HG) (5 mM) or vehicle control for 3 d, followed byimmunofluorescence assay to determine the 5hmC level, 2-HG treatment decreased the 5hmC level.
D-α-Hydroxyglutaric acid purchased from MedChemExpress. Usage Cited in: Nat Commun. 2025 Dec 16;16(1):11420. [Abstract]
D-α-Hydroxyglutaric acid disodium(2-HG; 5 mM; 1, 3, 5, 7 days) inhibited cell proliferation in MSCs.
D-α-Hydroxyglutaric acid purchased from MedChemExpress. Usage Cited in: Nat Commun. 2025 Dec 16;16(1):11420. [Abstract]
D-α-Hydroxyglutaric acid disodium(2-HG; 5 mM; 14 days) suppressed the differentiation into osteoblasts and adipocytes.
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Biosensors (Basel)
2022 Jan 25;12(2):66. PMID: 35200327 -
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D-α-Hydroxyglutaric acid purchased from MedChemExpress. Usage Cited in: Research Square Preprint. 2024 Mar 20.
Early MSCs were treated with D-α-Hydroxyglutaric acid disodium (2-HG) (5 mM) or vehicle control for 3 d, followed by dot-blot assay.
Solvant et solubilité
H2O : ≥ 100 mg/mL (675.17 mM)
DMSO : ≥ 100 mg/mL (675.17 mM; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
* "≥" means soluble, but saturation unknown.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
* 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.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
* 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.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Pureté et documentation
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Fiche technique (275 KB)
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Références
[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
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| H2O / DMSO | 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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