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876150-14-0

876150-14-0 Structure

876150-14-0 Structure
IdentificationBack Directory
[Name]

Octyl-α-ketoglutarate
[CAS]

876150-14-0
[Synonyms]

Octyl-α-KG
Octyl-α-ketoglutarate
QNFIHKFBQFJVKV-UHFFFAOYSA-N
Octyl-.alpha.-ketoglutarate
Pentanedioic acid, 2-oxo-, 1-octyl ester
[Molecular Formula]

C13H22O5
[MDL Number]

MFCD31697747
[MOL File]

876150-14-0.mol
[Molecular Weight]

258.31
Chemical PropertiesBack Directory
[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
Safety DataBack Directory
[Symbol(GHS) ]


GHS02,GHS07
[Signal word ]

Danger
[Hazard statements ]

H225-H319-H336
[Precautionary statements ]

P210-P240-P241-P242-P243-P261-P264-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P312-P337+P313-P370+P378-P403+P233-P403+P235-P405-P501
Hazard InformationBack Directory
[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].
[storage]

Store at -20°C
[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.
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