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349631

Sigma-Aldrich

Dimethyl 2-oxoglutarate

96%

Synonym(s):

Dimethyl α-ketoglutarate

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5 G
€112.00

€112.00

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5 G
€112.00

About This Item

Linear Formula:
CH3O2CCH2CH2COCO2CH3
CAS Number:
13192-04-6
Molecular Weight:
174.15
MDL number:
MFCD00048052
UNSPSC Code:
12352100
PubChem Substance ID:
24861693
NACRES:
NA.22
form:
liquid
Assay:
96%

€112.00

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Quality Level

100

Assay

96%

form

liquid

refractive index

n20/D 1.439 (lit.)

bp

90-95 °C/0.4 mmHg (lit.)

density

1.203 g/mL at 25 °C (lit.)

functional group

ester
ketone

SMILES string

COC(=O)CCC(=O)C(=O)OC

InChI

1S/C7H10O5/c1-11-6(9)4-3-5(8)7(10)12-2/h3-4H2,1-2H3

InChI key

TXIXSLPEABAEHP-UHFFFAOYSA-N

Related Categories

General description

Dimethyl 2-oxoglutarate is a key intermediate formed during the Krebs cycle and an important nitrogen transporter in the biological metabolic pathways.[1] The electrochemical behavior of dimethyl-2-oxoglutarate has been investigated by cyclic voltammetry, square wave voltammetry and differential pulse voltammetry using a glassy carbon electrode.[1]

Application

Dimethyl 2-oxoglutarate can undergo cylocondensation with dinucleophiles, such as 1,2-phenylenediamine, 2-aminophenol and 2-aminobenzenethiol to form novel heterocycles.[2]
Dimethyl 2-oxoglutarate may be used to synthesize the conformationally constrained PNA (peptide nucleic acid) -monomer capable of binding thymine in a triplex motif.[3] It may be used in the synthesis of 4-aryl kainic acid analogs, via highly stereoselective Michael addition reaction with nitrostyrene.[4]

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBD7573V
STBF1024V
STBD6981V
STBD5556V
STBD1443V

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Daniela Gaglio et al.
Molecular systems biology, 7, 523-523 (2011-08-19)
Oncogenes such as K-ras mediate cellular and metabolic transformation during tumorigenesis. To analyze K-Ras-dependent metabolic alterations, we employed ¹³C metabolic flux analysis (MFA), non-targeted tracer fate detection (NTFD) of ¹⁵N-labeled glutamine, and transcriptomic profiling in mouse fibroblast and human carcinoma
An efficient synthesis of 4-aryl kainic acid analogs.
Maeda H, et al.
Tetrahedron, 55(4), 943-954 (1999)
Organic syntheses based on 2?oxoglutaric acid. V. Syntheses of novel 2H?1, 4?benzothiazines and a 2, 5?dihydro?1, 5?benzothiazepine.
Blitzke T, et al.
Journal of Heterocyclic Chemistry, 34(2), 453-455 (1997)
Afzal Shah et al.
Bioelectrochemistry (Amsterdam, Netherlands), 77(2), 145-150 (2009-09-22)
The electrochemical behaviour of dimethyl-2-oxoglutarate (MOG), a key intermediate in the Krebs cycle and an important nitrogen transporter in the metabolic pathways in biological processes, was investigated by cyclic voltammetry, square wave voltammetry and differential pulse voltammetry using a glassy
Nicholas Jones et al.
Nature communications, 10(1), 2042-2042 (2019-05-06)
Metabolic pathways that regulate T-cell function show promise as therapeutic targets in diverse diseases. Here, we show that at rest cultured human effector memory and central memory CD4+ T-cells have elevated levels of glycolysis and oxidative phosphorylation (OXPHOS), in comparison
View All Related Papers

Articles

Glutamine Metabolism in Cancer Cells

Sigma article discusses tumor cell metabolic pathways, focusing on aerobic glycolysis and mitochondrial activity.

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/449/386/product-dating-information-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. What is the recommended solvent for diluting product #349631-5g? Should it be diluted in DMSO, water, or a buffer such as PBS?

    1 answer

    1. The recommended solvents for this chemical are DMSO at a concentration of 30 mg/ml, ethanol at 30 mg/ml, and PBS (pH 7.2) at 10 mg/ml.

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  4. Hello, What is the concentration of this product in its liquid form? I see the molecular weight, but not the total concentration. How many grams were dissolved in the amount of solvent present?

    1 answer

    1. This product is supplied as a neat or pure liquid with a density of 1.203 g/mL and a molecular weight of 174.15 g/mol. The minimum purity is 96%, thus the molarity will vary slightly from lot to lot. The molarity can range from 6.63M (96%) to 6.9M (100%). The lot specific purity is reported on the Certificate of Analysis.

      Molarity = density/MW * 1000 * concentration of the specific lot.

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  5. Dear support, what is the shelf life of this product?

    1 answer

    1. This product is not assigned an expiration date or recommended retest date. Products with no expiration date or recommended retest date should be routinely inspected by customers to ensure they perform as expected. These products are also subject to a one year warranty from the date of shipment. For more information you may access the "Product Dating Information" document under "ADDITIONAL USEFUL DOCUMENTS ABOUT OUR PRODUCTS" at the bottom of the Quality Services page with this link: https://www.sigmaaldrich.com/life-science/quality-and-regulatory-management/quality-services.

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  6. Dear Support, At what temperature should it be stored?

    1 answer

    1. This product should be stored in room temperature. Store the product tightly closed under dry conditions.

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  7. Dear Support, What solvent was used to dissolve Dimethyl oxoglutarate? Thank you!

    1 answer

    1. Solubility testing is not performed on this product. According to various sources it is soluble in DMSO (30mg/mL), DMF (30 mg/mL), and Ethanol (30mg/mL). This information has not been validated.

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  8. What is dimethyl 2-oxoglutarate made up in?

    1 answer

    1. This product is not diluted with any solvent. The physical form is a liquid. It is considered a 'neat' product with a minimum purity of 96%. The density is 1.203 g/mL at room temperature. The product is sold by weight, the 5 gram package would be approx. 4.16 mL.

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  9. Dear support desk, Is dimethyl 2-oxoglutarate cat #349631 sterile liquid? Thank you in advance

    1 answer

    1. This product it is not sterile.

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