(2R)-Octyl-alpha-hydroxyglutarate

alpha-Hydroxyglutaric acid (2-HG, Cay-16374) is normally metabolized to 2-oxoglutarate by D- and L-2-hydroxyglutarate dehydrogenases. Mutations in these enzymes cause 2-hydroxyglutaric aciduria, a neurometabolic disorder. Recent studies have found that mutations in isocitrate dehydrogenase 1 (IDH1) and IDH2, typically associated with certain cancers, can cause these enzymes to convert isocitrate to 2-HG, rather than alpha-ketoglutarate. 2-HG is structurally similar to alpha-ketoglutarate and competitively inhibits alpha-ketoglutarate-dependent dioxygenases, including lysine demethylases and DNA hydroxylases. (2R)-Octyl-alpha-hydroxyglutarate is a cell-permeable derivative of the D-isomer of 2-HG. It has been used to examine the contribution of D-2HG to the oxidative mitochondrial processes of IDH1-mutated cancer cells.Formal Name: 2R-hydroxy-pentanedioic acid, 1-octyl ester. CAS Number: 1391194-67-4. Synonyms: (2R)-Octyl-2-HG. Molecular Formula: C13H24O5. Formula Weight: 260.3. Purity: >95%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 10 mg/ml, DMSO: 10 mg/ml, Ethanol: 20 mg/ml, PBS (pH 7.2): 1 mg/ml. SMILES: OC(CC[C@@H](O)C(OCCCCCCCC)=O)=O. InChi Code: 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-/m1/s1. InChi Key: UJZOKTKSGUOCCM-LLVKDONJSA-N.