SML2563

TFMB-(S)-2HG

≥98% (HPLC)

• Synonym(s): (2S)-Tetrahydro-5-oxo-2-furancarboxylic acid, [3-(trifluoromethyl)phenyl]methyl ester, (S)-2-HG-TFMB, (S)-2HG-TFMB, (S)-3-(Trifluoromethyl)benzyl 5-oxotetrahydrofuran-2-carboxylate, (S)-TFMB-2-HG, (S)-TFMB-2HG, (S)-TFMB-OTC, TFMB-(S)-2-HG, TFMB-L2HG, Trifluoromethylbenzyl-(S)-2-HG
• Empirical Formula (Hill Notation): C₁₃H₁₁F₃O₄
• CAS Number: 1445703-64-9
• Molecular Weight: 288.22
• UNSPSC Code: 12352200
• NACRES: NA.77
• Assay: ≥98% (HPLC)
• Form: powder

Properties

• assay: ≥98% (HPLC)
• form: powder
• color: white to beige
• solubility: DMSO: 2 mg/mL, clear
• storage temp.: −20°C
• SMILES string: FC(F)(F)c1cc(ccc1)COC(=O)[C@H]2OC(=O)CC2
• InChI key: UXTLNUGKDZMPTC-JTQLQIEISA-N

Description

Biochem/physiol Actions

Membrane-permeant ester precursor of (S)-2-hydroxyglutarate (L-2HG) with distinct cellular activity as the oncometabolite (R)-2HG (D-2HG).

TFMB-(S)-2HG is a membrane-permeant (S)-2-hydroxyglutarate (L-2HG) precursor used in conjunction with the oncometabolite (R)-2-hydroxyglutarate (D-2HG) precursor for probing 2-HG enantiomer-specific cellular responses (typical conc used in culture: 0.5-20 mM). While both 2HG enantiomers inhibit multiple α-ketoglutarate (α-KG; 2-OG)-dependent dioxygenases by competing against α-KG binding, (S)-2HG is reported to be more potent against TET1/2, CeKDM7A & KDM5B (JARID1B/PLU-1). On the other hand, (R)-2HG, but not (S)-2HG, is shown to downregulate HIF-1a by promoting EglN1 (HIF prolyl hydroxylase 2; HIF-PH2; PHD2) activity.

Safety Information

• Storage Class: 13 - Non Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable