ETaKG

SIGMA/SML1743 - ≥95% (HPLC)

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

CAS Number: 2122289-21-6
Empirical Formula (Hill Notation): C₁₅H₁₅F₃O₅
Molecular Weight: 332.27
Linear Formula: C₁₅H₁₅F₃O₅
Product Type: Chemical

Catalog Number	PKG Qty.	Price


45-SML1743-5MG	5 mg	$125.00 1/EA	Add To Favorites
45-SML1743-25MG	25 mg	$511.00 1/EA	Add To Favorites

Properties
Descriptions
Safety Info.
Basic Data

assay	≥95% (HPLC)
color	colorless to light yellow
form	oil
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
InChI key	OKDCLZOKKGLMIX-UHFFFAOYSA-N
Quality Level	100
SMILES string	O=C(C(CCC(OCC)=O)=O)OCC1=CC=CC(C(F)(F)F)=C1
storage temp.	2-8°C

Biochem/physiol Actions:

A cell-permeable, bioavailable & aqueous stable α-ketoglutarate prodrug that selectively induces PHD-dependent cell death in hypoxic cells

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.

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

Purity	≥95% (HPLC)
Storage Temp.	2-8°C
UNSPSC	12352200

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