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| | Octyl-α-ketoglutarate Basic information |
| Product Name: | Octyl-α-ketoglutarate | | Synonyms: | Octyl-α-ketoglutarate;QNFIHKFBQFJVKV-UHFFFAOYSA-N;Octyl-.alpha.-ketoglutarate;Octyl-α-KG;Pentanedioic acid, 2-oxo-, 1-octyl ester;Octyl-α-ketoglutarate (α-KG octyl ester);Octyl-a-ketoglutarate (>90%);Octyl-α-KG | | CAS: | 876150-14-0 | | MF: | C13H22O5 | | MW: | 258.31 | | EINECS: | | | Product Categories: | | | Mol File: | 876150-14-0.mol |  |
| | Octyl-α-ketoglutarate Chemical Properties |
| Boiling point | 391.8±25.0 °C(Predicted) | | density | 1.083±0.06 g/cm3(Predicted) | | storage temp. | -20°C | | solubility | Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) | | form | oil | | pka | 4.07±0.17(Predicted) | | color | colorless to yellow | | Stability: | Hygroscopic | | InChI | 1S/C13H22O5/c1-2-3-4-5-6-7-10-18-13(17)11(14)8-9-12(15)16/h2-10H2,1H3,(H,15,16) | | InChIKey | QNFIHKFBQFJVKV-UHFFFAOYSA-N | | SMILES | CCCCCCCCOC(C(CCC(O)=O)=O)=O |
| WGK Germany | WGK 3 | | Storage Class | 11 - Combustible Solids |
| | Octyl-α-ketoglutarate Usage And Synthesis |
| Uses | Octyl-α-ketoglutarate is a prolyl hydroxylases substrate which accumulates rapidly in cells with dysfunctional tricarboxylic acid cycle. Octyl-α-ketoglutarate also prevents succinate or fumarate mediated inhibition of prolyl hydroxylases. | | Biological Activity | octyl-α-ketoglutarate is a stable, cell-permeable form of α-ketoglutarate, a substrate of prolyl hydroxylases (phd) [1][2].the high turnover of hifα is initiated by prolyl hydroxylases (phd), which hydroxylate proline residues on the oxygen-dependent degradation (odd) domain of hifα, facilitating ubiquitination and degradation. to catalyze proline hydroxylation, phds convert molecular oxygen and α-ketoglutarate to carbon dioxide and succinate [2]. loss of idh1 activity would reduce cellular levels of α-kg [3].octyl-α-ketoglutarate is a cell-permeating α-ketoglutarate derivative, which built up rapidly and preferentially in cells with a dysfunctional tca cycle. octyl-α-ketoglutarate increased intracellular levels of freeα-ketoglutaric acid by approximately fourfold. in hek293-derived cell lines expressing both a gfp-odd fusion protein and ha-tagged pvhl, octyl-α-ketoglutarate reactivated phd activity inhibited by succinate or fumarate. octyl-α-ketoglutarate restored hydroxylation and targeted hif1 for ubiquitylation and proteasomally mediated degradation [2]. octyl-α-ketoglutarate inhibited the hif-1α induction caused by idh1 knockdown in hela cells or overexpression of idh1r132h mutant in u-87mg cells, suggesting a reduction in idh1 activity caused a reduction in α-kg levels that in turn led to stabilization of hif-1α [3]. | | references | [1]. gottlieb e, tomlinson ip. mitochondrial tumour suppressors: a genetic and biochemical update. nat rev cancer. 2005 nov;5(11):857-66.
[2]. mackenzie ed, selak ma, tennant da, et al. cell-permeating alpha-ketoglutarate derivatives alleviate pseudohypoxia in succinate dehydrogenase-deficient cells. mol cell biol. 2007 may;27(9):3282-9.
[3]. zhao s, lin y, xu w, et al. glioma-derived mutations in idh1 dominantly inhibit idh1 catalytic activity and induce hif-1alpha. science. 2009 apr 10;324(5924):261-5. |
| | Octyl-α-ketoglutarate Preparation Products And Raw materials |
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