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SML3737

Sigma-Aldrich

Octyl-(S)-2HG

≥98% (HPLC)

Synonyma:

(2S)-2-Hydroxyglutarate octyl ester, (2S)-Octyl-α-hydroxyglutarate, (S)-4-Hydroxy-5-(octyloxy)-5-oxopentanoic acid, 1-Octyl-L-2-hydroxyglutarate, 2S-Hydroxy-pentanedioic acid, 1-octyl ester, L-Octyl-2HG, L2HG, Octyl-(S)-2-hydroxyglutarate, Octyl-L-2HG, S-2HG octyl ester

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About This Item

Empirický vzorec (Hillův zápis):
C13H24O5
Číslo CAS:
1391194-64-1
Molekulová hmotnost:
260.33
MDL number:
MFCD29045545
UNSPSC Code:
12352200
NACRES:
NA.21

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

-10 to -25°C

Biochem/physiol Actions

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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D J Wilson et al.
American journal of ophthalmology, 103(2), 167-179 (1987-02-15)
We studied 49 eyes obtained post mortem from 43 patients who had previously had retinal detachment surgery to evaluate some of the factors known to complicate retinal detachment. The retina had been successfully reattached in 44 of 49 eyes. We
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Journal of molecular biology, 429(19), 2895-2906 (2017-08-23)
Methylation of lysine-4 of histone H3 (H3K4men) is an important regulatory factor in eukaryotic transcription. Removal of the transcriptionally activating H3K4 methylation is catalyzed by histone demethylases, including the Jumonji C (JmjC) KDM5 subfamily. The JmjC KDMs are Fe(II) and
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We discovered recently that the central metabolite α-ketoglutarate (α-KG) extends the lifespan of C. elegans through inhibition of ATP synthase and TOR signaling. Here we find, unexpectedly, that (R)-2-hydroxyglutarate ((R)-2HG), an oncometabolite that interferes with various α-KG-mediated processes, similarly extends
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