An α-hydroxy acid
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D-α-Hydroxyglutaric Acid

Item No. 25895

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2R-hydroxy-pentanedioic acid
CAS Number
13095-47-1
Synonyms
  • DGA
  • D-2-HG
  • D-2-Hydroxyglutaric Acid
Molecular Formula
C5H8O5
Formula Weight
148.1
Purity
≥95%
Formulation (Request formulation change)
A 10 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
212 nm
SMILES
OC([C@@H](CCC(O)=O)O)=O
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-/m1/s1
InChi Key
HWXBTNAVRSUOJR-GSVOUGTGSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $36

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    5 mg

    $110

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    10 mg

    $153

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    25 mg

    $268

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    Product Description

    D-α-Hydroxyglutaric acid (D-2-HG) is an α-hydroxy acid.1 It decreases the oxygen consumption rate (OCR) and ratio of ATP to ADP in U87 glioma cells when used at a concentration of 800 µM. D-2-HG (100 µM) increases the levels of thiobarbituric acid reactive substances (TBARS) in isolated rat cerebral cortex homogenates.2 Urinary levels of D-2-HG are increased in D-2-hydroxyglutaric aciduria, a neurometabolic disease characterized by epilepsy, muscle hypotonia, and delays in psychomotor development.3,4 D-2-HG is structurally similar to α-ketoglutarate, the product of wild-type isocitrate dehydrogenases, and competitively inhibits α-ketoglutarate-dependent dioxygenases, including histone lysine demethylases and DNA hydroxylases.5,6,7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fu, X., Chin, R.M., Vergnes, L., et al. 2-Hydroxyglutarate inhibits ATP synthase and mTOR signaling. Cell Metab. 22(3), 508-515 (2015).

    2. Latini, A., Scussiato, K., Rosa, R.B., et al. D-2-hydroxyglutaric acid induces oxidative stress in cerebral cortex of young rats. Eur. J. Neurosci. 17(10), 2017-2022 (2003).

    3. Kranendijk, M., Struys, E.A., Van Schaftingen, E., et al. IDH2 Mutations in Patients with D-2-Hydroxyglutaric Aciduria. Science 330(6002), 336 (2014).

    4. Struys, E.A., Salomons, G.S., Achouri, Y., et al. Mutations in the D-2-hydroxyglutarate dehydrogenase gene cause D-2-hydroxyglutaric aciduria. Am. J. Hum. Genet. 76(2), 358-360 (2005).

    5. Yang, H., Ye, D., Guan, K.L., et al. IDH1 and IDH2 mutations in tumorigenesis: Mechanistic insights and clinical perspectives. Clin. Cancer Res. 18(20), 5562-5571 (2012).

    6. Xu, W., Yang, H., Liu, Y., et al. Oncometabolite 2-hydroxyglutarate is a competitive inhibitor of α-ketoglutarate-dependent dioxygenases. Cancer Cell 19(1), 17-30 (2011).

    7. Chowdhury, R., Yeoh, K.K., Tian, Y.M., et al. The oncometabolite 2-hydroxyglutarate inhibits histone lysine demethylases. EMBO Rep. 12(5), 463-469 (2011).