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SML3737

Sigma-Aldrich

Octyl-(S)-2HG

≥98% (HPLC)

Synonym(s):

(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

Empirical Formula (Hill Notation):
C13H24O5
CAS Number:
1391194-64-1
Molecular Weight:
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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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D J Wilson et al.
American journal of ophthalmology, 103(2), 167-179 (1987-02-15)
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Hanna Tarhonskaya et al.
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
Xudong Fu et al.
Cell metabolism, 22(3), 508-515 (2015-07-21)
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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Cell metabolism, 35(1), 200-211 (2022-10-30)
Despite its central importance in cellular metabolism, many details remain to be determined regarding subcellular lactate metabolism and its regulation in physiology and disease, as there is sensitive spatiotemporal resolution of lactate distribution, and dynamics remains a technical challenge. Here
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