SML2205

Octyl-α-KG

≥95% (HPLC), α-ketoglutarate precursor, oil

• Synonym(s): α-KG octyl ester, α-Ketoglutarate octyl ester, 1-Octyl-2-Oxo-pentanedioate, 1-Octyl-2-ketoglutarate, 2-Oxo-pentanedioic acid, 1-octyl ester, Octyl-α-ketoglutarate, Octyl-2KG
• Empirical Formula (Hill Notation): C₁₃H₂₂O₅
• CAS Number: 876150-14-0
• Molecular Weight: 258.31
• UNSPSC Code: 12352200
• NACRES: NA.77
• Assay: ≥95% (HPLC)
• Form: oil
• Storage condition: desiccated, under inert gas

Properties

• Product Name: Octyl-α-KG, ≥95% (HPLC)
• assay: ≥95% (HPLC)
• form: oil
• storage condition: desiccated, under inert gas
• color: colorless to yellow
• storage temp.: −20°C
• SMILES string: CCCCCCCCOC(C(CCC(O)=O)=O)=O
• InChI: 1S/C13H22O5/c1-2-3-4-5-6-7-10-18-13(17)11(14)8-9-12(15)16/h2-10H2,1H3,(H,15,16)
• InChI key: QNFIHKFBQFJVKV-UHFFFAOYSA-N

Description

Application

Octyl-α-KG has been used to study its effects on the cell viability and to replenish α-KG levels in human glioblastoma cells.

Biochem/physiol Actions

Membrane-permeant precursor of α-ketoglutarate that restores activity of α-KG-dependent dioxygenases in cancer cells.

Octyl-α-KG (Octyl-2KG) is a membrane-permeant precursor form of α-ketoglutarate (α-KG or 2KG) whose downregulation is often seen with concomitant upregulated D-2-hydroxyglutarate (D-2HG) in tumor cells due to mutations in the NADP⁺-dependent isocitrate dehydrogenase genes IDH1 and IDH2, leading to reduced activity of multiple α-KG-dependent dioxygenases. Cellular α-KG delivery by Octyl-α-KG treatment (1-5 mM) is shown to restore cellular demethylase activity following octyl-2-HG (1-50 mM) treatment or IDH1(R132H) mutant expression. Octyl-α-KG also effectively reactivates α-KG-dependent dioxygenases prolyl hydroxylase (PHD) activity in cells with a dysfunctional tricarboxylic acid (TCA) cycle due to succinate dehydrogenase (SDH) and/or fumarate hydratase (FH) deficiency.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable