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About This Item
Empirical Formula (Hill Notation):
C13H24O5
CAS Number:
Molecular Weight:
260.33
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.21
Product Name
Octyl-(S)-2HG, ≥98% (HPLC)
Quality Level
Assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 2 mg/mL, clear
storage temp.
-10 to -25°C
SMILES string
O[C@@H](CCC(=O)O)C(=O)OCCCCCCCC
InChI
1S/C13H24O5/c1-2-3-4-5-6-7-10-18-13(17)11(14)8-9-12(15)16/h11,14H,2-10H2,1H3,(H,15,16)/t11-/m0/s1
InChI key
UJZOKTKSGUOCCM-NSHDSACASA-N
Biochem/physiol Actions
Membrane-permeant precursor form of the oncometabolite L-2-hydroxyglutarate that inhibits α-ketoglutarate/α-KG-dependent dioxygenases.
Octyl-(S)-2HG (Octyl-L-2HG) is a membrane-permeant precursor form of the oncometabolite L-2-hydroxyglutarate (L2HG) produced from α‐KG by malate dehydrogenases (MDH1/2) and lactate dehydrogenase (LDHA). L2HG can be converted back to α-KG by L-2-hydroxyglutarate dehydrogenase (LHGDH), deletion or mutations of which lead to L2HG accumulation, metabolic disorders and reduced 5hmC levels. Both D- and L-2HG inhibit Jumonji histone demethylases and Tet oxygenases by competing against α-KG binding. However, L2HG is an antagonist, while R2HG (D2HG) is an agonist of α-KG-dependent prolylhydroxylase (EglN).
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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