A cell-permeable form of α-ketoglutarate
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5-Octyl-α-ketoglutarate

Item No. 16105

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-oxo-pentanedioic acid, 5-octyl ester
CAS Number
1616344-00-3
Synonyms
  • α-KG octyl ester
Molecular Formula
C13H22O5
Formula Weight
258.3
Purity
≥98%
Formulation (Request formulation change)
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
CCCCCCCCOC(CCC(C(O)=O)=O)=O
InChi Code
InChI=1S/C13H22O5/c1-2-3-4-5-6-7-10-18-12(15)9-8-11(14)13(16)17/h2-10H2,1H3,(H,16,17)
InChi Key
SZEOIQZPNSBRJC-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $99

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    5 mg

    $470

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    10 mg

    $840

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    Cayman Chemical
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    Product Description

    5-Octyl-α-ketoglutarate, also known as α-ketoglutarate octyl ester, is a stable, cell-permeable molecule that generates free α-ketoglutarate upon hydrolysis of the ester bond by cytoplasmic esterases.1 It is used in experiments to increase levels of intracellular α-ketoglutarate.1 5-Octyl-α-ketoglutarate has been shown to modulate a variety of enzymes and signaling pathways, particularly in the context of glycolysis, hypoxia, and cancer.1,2,3,4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. MacKenzie, E.D., Selak, M.A., Tennant, D.A., et al. Cell-permeating α-ketoglutarate derivatives alleviate pseudohypoxia in succinate dehydrogenase-deficient cells. Mol. Cell. Biol. 27(9), 3282-3289 (2007).

    2. 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).

    3. Xiao, M., Yang, H., Xu, W., et al. Inhibition of α-KG-dependent histone and DNA demethylases by fumarate and succinate that are accumulated in mutations of FH and SDH tumor suppressors. Genes Dev. 26(12), 1326-1338 (2012).

    4. Eckle, T., Brodsky, K., Bonney, M., et al. HIF1A reduces acute lung injury by optimizing carbohydrate metabolism in the alveolar epithelium. PLoS Biol. 11(9), 1-25 (2013).

    5. Chin, R.M., Fu, X., Pai, M.Y., et al. The metabolite α-ketoglutarate extends lifespan by inhibiting ATP synthase and TOR. Nature 509(7505), 397-401 (2014).