![2-Deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-D-glucose ≥97% (HPLC)](/deepweb/assets/sigmaaldrich/product/structures/104/527/40bd5a41-ebc4-484e-a10e-891fecfaea79/640/40bd5a41-ebc4-484e-a10e-891fecfaea79.png)
There is no information on the solution stability of aqueous solutions of this product. So it would be best to prepare fresh solutions as needed.
D6134
2-Deoxy-D-glucose
≥99% (GC), crystalline
Synonym(s):
2-Deoxy-D-arabinohexose
Sign Into View Organizational & Contract Pricing
All Photos(5)
About This Item
Empirical Formula (Hill Notation):
C6H12O5
CAS Number:
Molecular Weight:
164.16
Beilstein:
1723331
EC Number:
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.25
Pricing and availability is not currently available.
Recommended Products
biological source
synthetic (organic)
Quality Level
Assay
≥99% (GC)
form
crystalline
technique(s)
gas chromatography (GC): suitable
color
white
mp
146-147 °C (lit.)
solubility
H2O: soluble 330 mg/mL, clear, colorless
storage temp.
2-8°C
SMILES string
OC[C@@H](O)[C@@H](O)[C@H](O)CC=O
InChI
1S/C6H12O5/c7-2-1-4(9)6(11)5(10)3-8/h2,4-6,8-11H,1,3H2/t4-,5-,6+/m1/s1
InChI key
VRYALKFFQXWPIH-PBXRRBTRSA-N
Looking for similar products? Visit Product Comparison Guide
Application
2-Deoxy-D-glucose (2-DG) is used in glucoprivic feeding research to invoke and study the processes of counter-regulatory response (CRR). 2-Deoxy-D-glucose is used in the development of anti-cancer strategies that involve radio- and chemosensitization and oxidative stress.
Biochem/physiol Actions
2-Deoxy-D-Glucose (2-Deoxyglucose) is a glucose analog that inhibits glycolysis via its actions on hexokinase, the rate limiting step of glycolysis. It is phosphorylated by hexokinase to 2-DG-P which can not be further metabolized by phosphoglucose isomerase. This leads to the accumulation of 2-DG-P in the cell and the depletion in cellular ATP. In vitro, 2-Deoxyglucose has been shown to induce autophagy, increase ROS production, and activate AMPK.
Preparation Note
A further purification of the Grade II material by recrystallization.
Other Notes
To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Choose from one of the most recent versions:
Certificates of Analysis (COA)
Lot/Batch Number
Don't see the Right Version?
If you require a particular version, you can look up a specific certificate by the Lot or Batch number.
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
Customers Also Viewed
Alfredo J Ibáñez et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(22), 8790-8794 (2013-05-15)
Single-cell level measurements are necessary to characterize the intrinsic biological variability in a population of cells. In this study, we demonstrate that, with the microarrays for mass spectrometry platform, we are able to observe this variability. We monitor environmentally (2-deoxy-D-glucose)
Rosemarie Ungricht et al.
The Journal of cell biology, 209(5), 687-703 (2015-06-10)
Newly synthesized membrane proteins are constantly sorted from the endoplasmic reticulum (ER) to various membranous compartments. How proteins specifically enrich at the inner nuclear membrane (INM) is not well understood. We have established a visual in vitro assay to measure
Paramita Chakraborty et al.
Cell reports, 28(7), 1879-1893 (2019-08-15)
Sphingosine 1-phosphate (S1P), a bioactive lysophospholipid generated by sphingosine kinase 1 (SphK1), regulates lymphocyte egress into circulation via S1P receptor 1 (S1PR1) signaling, and it controls the differentiation of regulatory T cells (Tregs) and T helper-17 cells. However, the mechanisms by
Melissa A Burmeister et al.
American journal of physiology. Endocrinology and metabolism, 304(7), E677-E685 (2013-01-24)
Glucagon-like peptide-1 (GLP-1) suppresses food intake via activation of a central (i.e., brain) GLP-1 receptor (GLP-1R). Central AMP-activated protein kinase (AMPK) is a nutrient-sensitive regulator of food intake that is inhibited by anorectic signals. The anorectic effect elicited by hindbrain
Isaline Rowe et al.
Nature medicine, 19(4), 488-493 (2013-03-26)
Autosomal dominant polycystic kidney disease (ADPKD) is a common genetic disorder characterized by bilateral renal cyst formation. Recent identification of signaling cascades deregulated in ADPKD has led to the initiation of several clinical trials, but an approved therapy is still
Articles
We presents an article on Autophagy in Cancer Promotes Therapeutic Resistance
-
CAN THIS PRODUCT BE PREPARED IN WATER, AND FROZEN IN ALIQUOTS FOR LONG-TERM STORAGE?
1 answer-
Helpful?
-
-
Can this product be prepared in DMSO, and frozen in aliquots for long-term storage?
1 answer-
The chemical can be solubilized in DMSO (up to 190 mg/ml). Per literature reference, 1 M stock solutions of 2-deoxyglucose can be stored at -20 °C. Brandizzi, F., et al., Membrane Protein Transport between the Endoplasmic Reticulum and the Golgi in Tobacco Leaves Is Energy Dependent but Cytoskeleton Independent: Evidence from Selective Photobleaching. The Plant Cell, 14, 1293-1309 (2002). (Direct link to paper: http://www.plantcell.org/content/14/6/1293.full)
Helpful?
-
-
What is the shelf life of 2-Deoxy-D-glucose, Product D6134?
1 answer-
There is no recommended retest date given to released lots for this product. The product is guaranteed to be of good quality for one year from the time you receive it; this guarantee applies only to unopened bottles which have been stored at room temperature.
Helpful?
-
-
How can I dissolve 2-Deoxy-D-glucose, Product D6134?
1 answer-
The product is soluble in water at 330 mg/mL. It may also be soluble in DMSO.
Helpful?
-
-
What are the differences between products D6134 and D8375 which are both 2-deoxy-D-glucose?
1 answer-
Product D6134 is a further purification by crystallization of D8375.
Helpful?
-
-
Can solutions of 2-Deoxy-D-glucose, Product D6134, be stored?
1 answer-
Sigma-Aldrich has no information on the solution stability of this product. If information can't be found in the literature, it is best to prepare fresh solutions.
Helpful?
-
-
What is the Department of Transportation shipping information for this product?
1 answer-
Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
Helpful?
-
Active Filters
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
