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Merck

D6134

2-Désoxy-D-glucose

≥99% (GC), crystalline

Synonyme(s) :

2-Désoxy-D-arabinohexose

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250 MG

72.10 CHF

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151.00 CHF

5 G

420.00 CHF

25 G

1 900.00 CHF

72.10 CHF

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A propos de cet article

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

Principaux documents

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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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Cet article
D8375D3179M9376
2-Désoxy-D-glucose ≥99% (GC), crystalline

Sigma-Aldrich

D6134

2-Désoxy-D-glucose

2-Désoxy-D-glucose ≥98% (GC), crystalline

Sigma-Aldrich

D8375

2-Désoxy-D-glucose

2-Désoxy-D-glucose ≥98% (GC), BioXtra

Sigma-Aldrich

D3179

2-Désoxy-D-glucose

Méthyl α-D-glucopyranoside ≥99% (GC)

Sigma-Aldrich

M9376

Méthyl α-D-glucopyranoside

biological source

synthetic (organic)

biological source

synthetic

biological source

synthetic (organic)

biological source

synthetic (organic)

assay

≥99% (GC)

assay

≥98% (GC)

assay

≥98% (GC)

assay

≥99% (GC)

technique(s)

gas chromatography (GC): suitable

technique(s)

gas chromatography (GC): suitable, inhibition assay: suitable

technique(s)

gas chromatography (GC): suitable

technique(s)

gas chromatography (GC): suitable

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

solubility

H2O: soluble 330 mg/mL, clear, colorless

solubility

H2O: 0.250 g/5mL

solubility

H2O: 1 M at 20 °C, clear, colorless

solubility

water: 50 mg/mL, clear, colorless

form

crystalline

form

crystalline

form

powder

form

solid

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.

Consulter la Bibliothèque de documents

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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Questions

1–9 of 9 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  3. CAN THIS PRODUCT BE PREPARED IN WATER, AND FROZEN IN ALIQUOTS FOR LONG-TERM STORAGE?

    1 answer

    1. 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.

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  4. Can this product be prepared in DMSO, and frozen in aliquots for long-term storage?

    1 answer

    1. 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)

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

    1 answer

    1. 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.

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

    1 answer

    1. 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.

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

    1 answer

    1. Product D6134 is a further purification by crystallization of D8375.

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

    1 answer

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

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

    1 answer

    1. 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.

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