| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
| ln Vitro |
L-2-Hydroxyglutarate significantly inhibits 2-oxoglutarate (2-OG)-dependent dioxygenases (2OGD), including eleven-eleven translocation (TET) enzymes [1].
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|---|---|
| Toxicity/Toxicokinetics |
Toxicity Summary
2-Hydroxyglutarate is a carcinogenic metabolite. It is a competitive inhibitor of several α-ketoglutarate-dependent dioxygenases, including histone demethylases and 5-methylcytosine (5mC) hydroxylases of the TET family. Therefore, high levels of 2-hydroxyglutarate lead to genome-wide alterations in histone and DNA methylation, ultimately resulting in cancer-inducing mutations. L-2-hydroxyglutarate exerts its neurotoxic effects by activating N-methyl-D-aspartate receptors. The structure of L-2-hydroxyglutarate is similar to the excitatory amino acid glutamate, and it stimulates neurodegeneration through known mechanisms such as glutamate, NMDA, or mitochondrial toxins (A15198). |
| References | |
| Additional Infomation |
(S)-2-hydroxyglutaric acid is a 2-hydroxyglutaric acid, the conjugate acid of (S)-2-hydroxyglutaric acid (2-), and also the enantiomer of (R)-2-hydroxyglutaric acid. L-2-hydroxyglutaric acid is a metabolite found or produced in Escherichia coli (strains K12 and MG1655). (2S)-2-hydroxyglutaric acid has been reported in humans and C. elegans, but relevant data are unclear. L-2-hydroxyglutaric acid is an α-hydroxy acid. In humans, this compound is produced by hydroxy acid-keto acid transhydrogenase; in bacteria, it is produced by 2-hydroxyglutaric acid synthase. This compound can be converted to α-ketoglutaric acid by the action of 2-hydroxyglutaric acid dehydrogenase. Two such enzymes exist in humans, called D2HGDH and L2HGDH. The accumulation of large amounts of D-2-hydroxyglutaric acid in tissues is a biochemical marker of D-2-hydroxyglutaric aciduria, a hereditary neurometabolic disorder. Both D- and L-hydroxyglutaric acid (EC 1.1.99.2) stereoisomers are present in body fluids. Many patients have been reported to have accumulated L-2-hydroxyglutaric acid, exhibiting a clinical phenotype of progressive neurodegeneration, accompanied by extrapyramidal and cerebellar signs, seizures, and spongiform changes in the white matter. Patients with excessive accumulation of D-2-hydroxyglutaric acid in their urine exhibit diverse phenotypes, including intellectual disability, macrocephaly with cerebral atrophy, hypotonia, seizures, and involuntary movements.
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| Molecular Formula |
C5H8O5
|
|---|---|
| Molecular Weight |
148.11400
|
| Exact Mass |
148.037
|
| CAS # |
13095-48-2
|
| Related CAS # |
L-2-Hydroxyglutaric acid disodium;63512-50-5
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| PubChem CID |
439939
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| Appearance |
Colorless to light yellow liquid
|
| Density |
1.508g/cm3
|
| Boiling Point |
394.2ºC at 760mmHg
|
| Flash Point |
206.4ºC
|
| Vapour Pressure |
7.55E-08mmHg at 25°C
|
| Index of Refraction |
1.519
|
| LogP |
-1
|
| Hydrogen Bond Donor Count |
3
|
| Hydrogen Bond Acceptor Count |
5
|
| Rotatable Bond Count |
4
|
| Heavy Atom Count |
10
|
| Complexity |
141
|
| Defined Atom Stereocenter Count |
1
|
| SMILES |
O=C(O)[C@@H](O)CCC(O)=O
|
| InChi Key |
HWXBTNAVRSUOJR-VKHMYHEASA-N
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| InChi Code |
InChI=1S/C5H8O5/c6-3(5(9)10)1-2-4(7)8/h3,6H,1-2H2,(H,7,8)(H,9,10)/t3-/m0/s1
|
| Chemical Name |
(2S)-2-hydroxypentanedioic acid
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 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 |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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