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D6134

Sigma-Aldrich

2-Deoxy-D-glucose

≥99% (GC), crystalline

Synonym(s):

2-Deoxy-D-arabinohexose

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About This Item

Empirical Formula (Hill Notation):
C6H12O5
CAS Number:
154-17-6
Molecular Weight:
164.16
Beilstein:
1723331
EC Number:
205-823-0
MDL number:
MFCD00151328
UNSPSC Code:
12352201
PubChem Substance ID:
24894000
NACRES:
NA.25

biological source

synthetic (organic)

Quality Level

200

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

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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

Regulatory Information

监管及禁止进口产品

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Certificates of Analysis (COA)

Lot/Batch Number
0000409984
0000371646
0000393208
0000373997
0000374010

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How can I dissolve 2-Deoxy-D-glucose, Product D6134?

    The product is soluble in water at 330 mg/mL.  It may also be soluble in DMSO.

  4. Can solutions of 2-Deoxy-D-glucose, Product D6134, be stored?

    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.

  5. What is the shelf life of 2-Deoxy-D-glucose, Product D6134?

    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.

  6. What are the differences between products D6134 and D8375 which are both 2-deoxy-D-glucose?

    Product D6134 is a further purification by crystallization of D8375.

  7. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  8. What is the Department of Transportation shipping information for this product?

    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. 

  9. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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
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)
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
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
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
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