SML2205
Octyl-α-KG
≥95% (HPLC)
Synonym(s):
α-KG octyl ester, α-Ketoglutarate octyl ester, 1-Octyl-2-Oxo-pentanedioate, 1-Octyl-2-ketoglutarate, 2-Oxo-pentanedioic acid, 1-octyl ester, Octyl-α-ketoglutarate, Octyl-2KG
Sign Into View Organizational & Contract Pricing
All Photos(1)
About This Item
Empirical Formula (Hill Notation):
C13H22O5
CAS Number:
Molecular Weight:
258.31
UNSPSC Code:
12352200
NACRES:
NA.77
Recommended Products
Assay
≥95% (HPLC)
form
oil
storage condition
desiccated
under inert gas
color
colorless to yellow
storage temp.
−20°C
SMILES string
CCCCCCCCOC(C(CCC(O)=O)=O)=O
Application
Octyl-α-KG has been used to study its effects on the cell viability and to replenish α-KG levels in human glioblastoma cells.
Biochem/physiol Actions
Octyl-α-KG (Octyl-2KG) is a membrane-permeant precursor form of α-ketoglutarate (α-KG or 2KG) whose downregulation is often seen with concomitant upregulated D-2-hydroxyglutarate (D-2HG) in tumor cells due to mutations in the NADP+-dependent isocitrate dehydrogenase genes IDH1 and IDH2, leading to reduced activity of multiple α-KG-dependent dioxygenases. Cellular α-KG delivery by Octyl-α-KG treatment (1-5 mM) is shown to restore cellular demethylase activity following octyl-2-HG (1-50 mM) treatment or IDH1(R132H) mutant expression. Octyl-α-KG also effectively reactivates α-KG-dependent dioxygenases prolyl hydroxylase (PHD) activity in cells with a dysfunctional tricarboxylic acid (TCA) cycle due to succinate dehydrogenase (SDH) and/or fumarate hydratase (FH) deficiency.
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’.
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
Customers Also Viewed
Shizhong Ke et al.
Hepatology (Baltimore, Md.), 65(1), 134-151 (2016-10-25)
Erythrocytosis is a common paraneoplastic syndrome associated with hepatocellular carcinoma. Although increased erythropoietin (EPO) is found in these patients, the clinical significance and molecular mechanisms underlying this observation are unclear. We demonstrate an inverse relationship between EPO production and overall
Elaine D MacKenzie et al.
Molecular and cellular biology, 27(9), 3282-3289 (2007-02-28)
Succinate dehydrogenase (SDH) and fumarate hydratase (FH) are components of the tricarboxylic acid (TCA) cycle and tumor suppressors. Loss of SDH or FH induces pseudohypoxia, a major tumor-supporting event, which is the activation of hypoxia-inducible factor (HIF) under normoxia. In
Shimin Zhao et al.
Science (New York, N.Y.), 324(5924), 261-265 (2009-04-11)
Heterozygous mutations in the gene encoding isocitrate dehydrogenase-1 (IDH1) occur in certain human brain tumors, but their mechanistic role in tumor development is unknown. We have shown that tumor-derived IDH1 mutations impair the enzyme's affinity for its substrate and dominantly
L Zeng et al.
Oncogene, 34(36), 4758-4766 (2014-12-23)
Cancer cells gain a growth advantage through the so-called Warburg effect by shifting glucose metabolism from oxidative phosphorylation to aerobic glycolysis. Hypoxia-inducible factor 1 (HIF-1) has been suggested to function in metabolic reprogramming; however, the underlying mechanism has not been
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
Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.
Contact Technical Service