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Merck
CN

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

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About This Item

Empirical Formula (Hill Notation):
C13H11F3O4
CAS Number:
1445703-64-9
Molecular Weight:
288.22
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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InChI key

UXTLNUGKDZMPTC-JTQLQIEISA-N

SMILES string

FC(F)(F)c1cc(ccc1)COC(=O)[C@H]2OC(=O)CC2

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

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.

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000162992
0000143929
0000071183
0000067256

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