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SML2200

Sigma-Aldrich

Octyl-(R)-2HG

≥98% (HPLC)

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Synonym(s):
(2R)-2-Hydroxyglutarate octyl ester, (2R)-Octyl-α-hydroxyglutarate, 1-Octyl-D-2-hydroxyglutarate, 1-octyl ester, 2R-Hydroxy-pentanedioic acid, Octyl-2HG, Octyl-D-2HG, R-2HG octyl ester
Empirical Formula (Hill Notation):
C13H24O5
CAS Number:
Molecular Weight:
260.33
MDL number:
NACRES:
NA.77

assay

≥98% (HPLC)

form

film

storage condition

desiccated

color

colorless

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

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SML2205O600410634425001
vibrant-m

SML2200

Octyl-(R)-2HG

vibrant-m

SML2205

Octyl-α-KG

vibrant-m

O6004

Octyl β-D-1-thioglucopyranoside

vibrant-m

10634425001

n-Octylglucoside

form

film

form

oil

form

crystalline

form

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

-

solubility

DMSO: 2 mg/mL, clear

solubility

-

solubility

-

solubility

-

color

colorless

color

colorless to yellow

color

-

color

-

storage condition

desiccated

storage condition

desiccated, under inert gas

storage condition

-

storage condition

-

Application

Octyl-(R)-2 hydroxyglutarate (HG) has been used as a membrane permeamble oncometabolite in gliblostoma cells to test its effects on NANOG transcription factor expression. It has also been used as a competitive inhibitor of the enzyme α-ketoglutarate (α-KG)-dependent deoxygenase.

Biochem/physiol Actions

Octyl-(R)-2HG (Octyl-D-2HG) is a membrane-permeant precursor form of the oncometabolite D-2-hydroxyglutarate (D-2HG) produced by tumor cells due to mutations in the NADP+-dependent isocitrate dehydrogenase genes IDH1 and IDH2. D-2HG inhibits multiple α-ketoglutarate/α-KG-dependent dioxygenases by competing against α-KG binding. Cellular D-2HG delivery by Octyl-(R)-2HG treatment (1-50 mM) is shown to suppress demethylase activity (~148% H3K9me2 and ~310% H3K79me2 upregulation; 50 mM in U-87MG) as well as increase HIF-1α and decrease endostatin levels as a result of inhibiting α-KG-dependent dioxygenases prolyl hydroxylases (PHDs) and collagen prolyl-4-hydroxylase (C-P4H), respectively.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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alpha-Ketoglutarate-Activated NF-$\kappa$B Signaling Promotes Compensatory Glucose Uptake and Brain Tumor Development
Wang X, et al.
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Zachary J Reitman et al.
The Journal of biological chemistry, 289(34), 23318-23328 (2014-07-06)
Mutations in the cytosolic NADP(+)-dependent isocitrate dehydrogenase (IDH1) occur in several types of cancer, and altered cellular metabolism associated with IDH1 mutations presents unique therapeutic opportunities. By altering IDH1, these mutations target a critical step in reductive glutamine metabolism, the
Jing-Yi Chen et al.
Scientific reports, 6, 32428-32428 (2016-09-01)
Mutations of isocitrate dehydrogenase 1 (IDH1) and IDH2 in acute myeloid leukemia (AML) cells produce the oncometabolite R-2-hydroxyglutarate (R-2HG) to induce epigenetic alteration and block hematopoietic differentiation. However, the effect of R-2HG released by IDH-mutated AML cells on the bone
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By impairing histone demethylation and locking cells into a reprogramming-prone state, oncometabolites can partially mimic the process of induced pluripotent stem cell generation. Using a systems biology approach, combining mathematical modeling, computation, and proof-of-concept studies with live cells, we found
Makoto Hirata et al.
Proceedings of the National Academy of Sciences of the United States of America, 112(9), 2829-2834 (2015-03-03)
Enchondromas are benign cartilage tumors and precursors to malignant chondrosarcomas. Somatic mutations in the isocitrate dehydrogenase genes (IDH1 and IDH2) are present in the majority of these tumor types. How these mutations cause enchondromas is unclear. Here, we identified the

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