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D6134

2-Desoxi-D-glucosa

≥99% (GC), crystalline

Sinónimos:

2-Desoxi-D-arabinohexosa

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Fórmula empírica (notación de Hill):
C6H12O5
Número CAS:
Peso molecular:
164.16
UNSPSC Code:
12352201
NACRES:
NA.25
PubChem Substance ID:
EC Number:
205-823-0
Beilstein/REAXYS Number:
1723331
MDL number:
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biological source

synthetic (organic)

Quality Segment

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

application(s)

advanced drug delivery

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

Application

La 2-desoxi-D-glucosa (2-DG) se utiliza en la alimentación glucoprívica para invocar y estudiar los procesos de respuesta contrarreguladora (CRR). La 2-desoxi-D-glucosa se utiliza en el desarrollo de estrategias antineoplásicas que implican radiosensibilización y quimiosensibilización y estrés oxidativo.

Biochem/physiol Actions

La 2-desoxi-D-glucosa (2-desoxiglucosa) es un análogo de la glucosa que inhibe la glucólisis a través de sus acciones sobre la hexoquinasa, la etapa limitante de la velocidad de la glucólisis. Es fosforilada por la hexoquinasa a 2-DG-P, que no puede ser metabolizada después por la fosfoglucoisomerasa. Esto provoca la acumulación de 2-DG-P en la célula y el agotamiento del ATP celular. In vitro, se ha demostrado que la 2-desoxiglucosa induce autofagia, aumenta la producción de ROS y activa la AMPK.

Preparation Note

Una ulterior purificación del material de grado II por recristalización.

Other Notes

Si desea conocer por completo nuestra amplia gama de monosacáridos para su investigación, le recomendamos que visite nuestra página de categoría Carbohidratos .

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Este artículo
D8375D3179M9376
biological source

synthetic (organic)

biological source

synthetic

biological source

synthetic (organic)

biological source

synthetic (organic)

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

assay

≥99% (GC)

assay

≥98% (GC)

assay

≥98% (GC)

assay

≥99% (GC)

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

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

form

crystalline

form

crystalline

form

powder

form

solid


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Clase de almacenamiento

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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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

      Helpful?

  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

      Helpful?

  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.

      Helpful?

  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)

      Helpful?

  5. 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.

      Helpful?

  6. 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.

      Helpful?

  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.

      Helpful?

  8. 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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  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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