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SML2205 Sigma-Aldrich

Octyl-α-KG

≥95% (HPLC)

Synonym: 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

  • CAS Number 876150-14-0

  • Empirical Formula (Hill Notation) C13H22O5

  • Molecular Weight 258.31

  •  NACRES NA.77

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, O
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

Description

Biochem/physiol Actions

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 upreguated 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 & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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