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
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About This Item
Empirical Formula (Hill Notation):
C13H22O5
CAS Number:
Molecular Weight:
258.31
UNSPSC Code:
12352200
NACRES:
NA.77
Assay:
≥95% (HPLC)
Form:
oil
Storage condition:
desiccated, under inert gas
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
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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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