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Merck

D6134

2-Désoxy-D-glucose

≥99% (GC), crystalline

Synonyme(s) :

2-Désoxy-D-arabinohexose

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About This Item

Formule empirique (notation de Hill) :
C6H12O5
Numéro CAS:
154-17-6
Poids moléculaire :
164.16
UNSPSC Code:
12352201
NACRES:
NA.25
PubChem Substance ID:
24894000
EC Number:
205-823-0
Beilstein/REAXYS Number:
1723331
MDL number:
MFCD00151328

Nom du produit

2-Désoxy-D-glucose, ≥99% (GC), crystalline

InChI key

VRYALKFFQXWPIH-PBXRRBTRSA-N

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

SMILES string

OC[C@@H](O)[C@@H](O)[C@H](O)CC=O

biological source

synthetic (organic)

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

Quality Level

200

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Catégories apparentées

Application

Le 2-désoxy-D-glucose (2-DG) est utilisé dans les recherches sur l′alimentation glucoprivique pour déclencher et étudier les processus de la réponse contre-régulatoire (CRR). Le 2-désoxy-D-glucose sert au développement de stratégies anticancéreuses impliquant une radio et une chimiosensibilisation et un stress oxydatif.

Biochem/physiol Actions

Le 2-désoxy-D-glucose (2-désoxyglucose) est un analogue du glucose qui inhibe la glycolyse de par son action sur l′hexokinase, l′étape cinétiquement limitante de la glycolyse. Il est phosphorylé par l′hexokinase en 2-DG-P, un composé qui ne peut pas être métabolisé à son tour par la phosphoglucose isomérase. Il s′ensuit une accumulation de 2-DG-P dans la cellule et une diminution de l′ATP cellulaire. Il a été montré in vitro que le 2-désoxyglucose induit l′autophagie, augmente la production de DRO et active l′AMPK.

Other Notes

Pour bien comprendre notre vaste gamme de monosaccharides et tout ce qu'elle peut apporter à vos recherches, nous vous encourageons à visiter notre page dédiée aux glucides.

Preparation Note

Purification supplémentaire du produit de grade II par recristallisation.

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

Lot/Batch Number
0000520789
0000520789
0000501836
0000501836
0000474155

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

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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.

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
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