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SML1743

Sigma-Aldrich

ETaKG

≥95% (HPLC)

Synonym(s):

2-Oxo-pentanedioic acid 5-ethyl ester 1-(3-trifluoromethyl-benzyl) ester, 5-Ethyl 1-(3-(trifluoromethyl)benzyl) 2-oxopentanedioate

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5 MG
$143.00
25 MG
$583.00

$143.00


Estimated to ship onMarch 29, 2025



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5 MG
$143.00
25 MG
$583.00

About This Item

Empirical Formula (Hill Notation):
C15H15F3O5
CAS Number:
Molecular Weight:
332.27
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

$143.00


Estimated to ship onMarch 29, 2025


Quality Level

Assay

≥95% (HPLC)

form

oil

color

colorless to light yellow

storage temp.

2-8°C

SMILES string

O=C(C(CCC(OCC)=O)=O)OCC1=CC=CC(C(F)(F)F)=C1

InChI

1S/C15H15F3O5/c1-2-22-13(20)7-6-12(19)14(21)23-9-10-4-3-5-11(8-10)15(16,17)18/h3-5,8H,2,6-7,9H2,1H3

Biochem/physiol Actions

ETaKG is a cell-permeable, aqueous stable, bioavailable, non-toxic α-ketoglutarate/2-oxoglutarate (α-KG/2-OG) diester derivative that readily undergoes hydrolysis by cytosolic esterases to α-KG. The monoester analog, TaKG is also membrane permeant. ETaKG elevates intracellular [α-KG] by ~15-fold in a prologned fashion, destabilizes HIF-1α/2α and reactivates prolyl hydroxylases (PHDs) in hypoxic HCT116, A431 and RPE cells at 2 mM. Further, shown to selectively trigger PHD-dependent cell death in hypoxic cells and decreases cellular [ATP] and glucose uptake. ETaKG has shown to reduce glucose metabolism, elevate [α-KG] levels and suppress A375 xenograft tumor growth (750 mg/kg of mice, p.o., q.d., 14 days). Also, induces mTORC1 lysosomal translocation and stimulates mTORC1 activity in the absence of glutaminolysis in U2OS cells.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Hanumantha Rao Madala et al.
Cancer research, 80(17), 3492-3506 (2020-07-12)
Under conditions of inherent or induced mitochondrial dysfunction, cancer cells manifest overlapping metabolic phenotypes, suggesting that they may be targeted via a common approach. Here, we use multiple oxidative phosphorylation (OXPHOS)-competent and incompetent cancer cell pairs to demonstrate that treatment

Questions

  1. Hi Can you please tell me about the solubility and the concentration of EtaKG ? DMSO ? Best regards Salwan

    1 answer
    1. This product is an oil, the solubility has not been tested. However, It is reportedly soluble in DMSO, acetonitrile, acetone, chloroform , dichloromethane. Avoid methanol and ethanol as this will cause the product to quickly degrade. For HPLC applications, DMSO is the preferred solvent. Please see the link below to review a publication that may be helpful:
      https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7484159/

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