An internal standard for the quantification of (2R)-octyl-α-hydroxyglutarate
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Unlabeled Version(s)
16366(2R)-Octyl-α-hydroxyglutarate
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(2R)-Octyl-α-hydroxyglutarate-d17

Item No. 19694

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2R-hydroxy-pentanedioic acid, 1-octyl-d17 ester
CAS Number
2748638-78-8
Synonyms
  • (2R)-Octyl-2-HG-d17
Molecular Formula
C13H7D17O5
Formula Weight
277.4
Purity
≥99% deuterated forms (d1-d17)
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlEthanol: 20 mg/mlPBS (pH 7.2): 1 mg/ml
SMILES
OC(CC[C@@H](O)C(OC([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])[2H])=O)=O
InChi Code
InChI=1S/C13H24O5/c1-2-3-4-5-6-7-10-18-13(17)11(14)8-9-12(15)16/h11,14H,2-10H2,1H3,(H,15,16)/t11-/m1/s1/i1D3,2D2,3D2,4D2,5D2,6D2,7D2,10D2
InChi Key
UJZOKTKSGUOCCM-XDYCJWJQSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

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    1 mg

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    5 mg

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    Cayman Chemical
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    Product Description

    α-Hydroxyglutaric acid (2-HG; Item No. 16374) is normally metabolized to 2-oxoglutarate by D- and L-2-hydroxyglutarate dehydrogenases. Mutations in these enzymes cause 2-hydroxyglutaric aciduria, a neurometabolic disorder.1,2,3 Recent studies have found that mutations in isocitrate dehydrogenase 1 (IDH1) and IDH2, typically associated with certain cancers, can cause these enzymes to convert isocitrate to 2-HG, rather than α-ketoglutarate.4,5 2-HG is structurally similar to α-ketoglutarate and competitively inhibits α-ketoglutarate-dependent dioxygenases, including lysine demethylases and DNA hydroxylases.5,6,7 (2R)-Octyl-α-hydroxyglutarate-d17 is intended for use as an internal standard for the quantification of (2R)-octyl-α-hydroxyglutarate (Item No. 16366) by GC- or LC-MS. (2R)-Octyl-α-hydroxyglutarate is a cell-permeable derivative of the D-isomer of 2-HG. It has been used to examine the contribution of D-2-HG to the oxidative mitochondrial processes of IDH1-mutated cancer cells.8

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Rzem, R., Veiga-da-Cunha, M., Noël, G., et al. A gene encoding a putative FAD-dependent L-2-hydroxyglutarate dehydrogenase is mutated in L-2-hydroxyglutaric aciduria. Proc. Natl. Acad. Sci. USA 101(48), 16849-16854 (2004).

    2. Struys, E.A., Verhoeven, N.M., Roos, B., et al. Disease-related metabolites in culture medium of fibroblasts from patients with D-2-hydroxyglutaric aciduria, L-2-hydroxyglutaric aciduria, and combined D/L-2-hydroxyglutaric aciduria. Clin. Chem. 49(7), 1133-1138 (2003).

    3. 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).

    4. Ward, P., Patel, J., Wise, D.R., et al. The common feature of leukemia-associated IDH1 and IDH2 mutations is a neomorphic enzyme activity converting α-ketoglutarate to 2-hydroxyglutarate. Cancer Cell 17(3), 225-234 (2010).

    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).

    8. Reitman, Z.J., Duncan, C.G., Poteet, E., et al. Cancer-associated isocitrate dehydrogenase 1 (IDH1) R132H mutation and d-2-hydroxyglutarate stimulate glutamine metabolism under hypoxia. The Journal of Biological Chemisty 289(34), 23318-23328 (2014).