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MedKoo Cat#: 464950 | Name: TUN-92046
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Dimethyl 2-ketoglutarate is an esterified form of the citric acid cycle intermediate α-ketoglutarate. It increases intracellular levels of α-ketoglutarate and decreases intracellular ATP levels in U2OS human osteosarcoma cells cultured in complete- or nutrient-free media when used at a concentration of 5 mM. Dimethyl 2-ketoglutarate inhibits autophagy and decreases in intracellular levels of acetyl-CoA in serum- and nutrient-deprived cells. It decreases cardiomyocyte hypertrophy in a mouse model of cardiac pressure overload induced by thoracic aortic constriction when administered at a dose of 300 mg/kg. Dimethyl 2-ketoglutarate reduces serum levels of aspartate aminotransferase (AST) and alanine aminotransferase (ALT) and hepatic fibrosis in a rat model of liver fibrosis induced by carbon tetrachloride (CCl4). This product has no formal name. For the convenience of scientific communication, we named it by combining its InChi Key (3 letters from the first letter of each section) with the last 5 digit of its CAS#) according to MedKoo Chemical Nomenclature (https://www.medkoo.com/page/naming).

Chemical Structure

TUN-92046
TUN-92046
CAS#13192-04-6

Theoretical Analysis

MedKoo Cat#: 464950

Name: TUN-92046

CAS#: 13192-04-6

Chemical Formula: C7H10O5

Exact Mass: 174.0528

Molecular Weight: 174.15

Elemental Analysis: C, 48.28; H, 5.79; O, 45.93

Price and Availability

Size Price Availability Quantity
500mg USD 210.00 2 Weeks
1g USD 430.00 2 Weeks
5g USD 540.00 2 Weeks
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Related CAS #
No Data
Synonym
TUN-92046; TUN92046; TUN 92046; Dimethyl 2-ketoglutarate; Dimethyl 2 ketoglutarate; 2-KG dimethyl ester; 2 KG dimethyl ester; Dimethyl α-ketoglutarate; Dimethyl α ketoglutarate; Dimethyl 2-oxoglutarate; Dimethyl 2 oxoglutarate;
IUPAC/Chemical Name
dimethyl 2-oxopentanedioate
InChi Key
TXIXSLPEABAEHP-UHFFFAOYSA-N
InChi Code
InChI=1S/C7H10O5/c1-11-6(9)4-3-5(8)7(10)12-2/h3-4H2,1-2H3
SMILES Code
COC(CCC(C(OC)=O)=O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Solvent mg/mL mM
Solubility
DMF 30.0 172.26
DMSO 30.0 172.26
Ethanol 30.0 172.26
PBS (pH 7.2) 10.0 57.42
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 174.15 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
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PMID: 31173576; PMCID: PMC6594794. 7: Sica V, Bravo-San Pedro JM, Izzo V, Pol J, Pierredon S, Enot D, Durand S, Bossut N, Chery A, Souquere S, Pierron G, Vartholomaiou E, Zamzami N, Soussi T, Sauvat A, Mondragón L, Kepp O, Galluzzi L, Martinou JC, Hess-Stumpp H, Ziegelbauer K, Kroemer G, Maiuri MC. Lethal Poisoning of Cancer Cells by Respiratory Chain Inhibition plus Dimethyl α-Ketoglutarate. Cell Rep. 2019 Apr 16;27(3):820-834.e9. doi: 10.1016/j.celrep.2019.03.058. PMID: 30995479. 8: Egnatchik RA, Leamy AK, Sacco SA, Cheah YE, Shiota M, Young JD. Glutamate- oxaloacetate transaminase activity promotes palmitate lipotoxicity in rat hepatocytes by enhancing anaplerosis and citric acid cycle flux. J Biol Chem. 2019 Mar 1;294(9):3081-3090. doi: 10.1074/jbc.RA118.004869. Epub 2018 Dec 18. PMID: 30563841; PMCID: PMC6398133. 9: Sivaramakrishnan R, Suresh S, Incharoensakdi A. Chlamydomonas sp. as dynamic biorefinery feedstock for the production of methyl ester and ɛ-polylysine. Bioresour Technol. 2019 Jan;272:281-287. doi: 10.1016/j.biortech.2018.10.026. Epub 2018 Oct 11. PMID: 30366287. 10: Yu S, Ding L, Liang D, Luo L. Porphyromonas gingivalis inhibits M2 activation of macrophages by suppressing α-ketoglutarate production in mice. Mol Oral Microbiol. 2018 Oct;33(5):388-395. doi: 10.1111/omi.12241. Epub 2018 Aug 19. PMID: 30007055. 11: Holeček M. Branched-chain amino acid supplementation in treatment of liver cirrhosis: Updated views on how to attenuate their harmful effects on cataplerosis and ammonia formation. Nutrition. 2017 Sep;41:80-85. doi: 10.1016/j.nut.2017.04.003. Epub 2017 Apr 19. PMID: 28760433. 12: Zhao J, Peng L, Cui R, Guo X, Yan M. Dimethyl α-ketoglutarate reduces CCl4-induced liver fibrosis through inhibition of autophagy in hepatic stellate cells. Biochem Biophys Res Commun. 2016 Dec 2;481(1-2):90-96. doi: 10.1016/j.bbrc.2016.11.010. Epub 2016 Nov 5. PMID: 27823933. 13: Peng Y, Alexov E. Cofactors-loaded quaternary structure of lysine-specific demethylase 5C (KDM5C) protein: Computational model. Proteins. 2016 Dec;84(12):1797-1809. doi: 10.1002/prot.25162. Epub 2016 Oct 1. PMID: 27696497; PMCID: PMC5118127. 14: Hwang IY, Kwak S, Lee S, Kim H, Lee SE, Kim JH, Kim YA, Jeon YK, Chung DH, Jin X, Park S, Jang H, Cho EJ, Youn HD. Psat1-Dependent Fluctuations in α-Ketoglutarate Affect the Timing of ESC Differentiation. Cell Metab. 2016 Sep 13;24(3):494-501. doi: 10.1016/j.cmet.2016.06.014. Epub 2016 Jul 28. PMID: 27476977. 15: Kuo CY, Cheng CT, Hou P, Lin YP, Ma H, Chung Y, Chi K, Chen Y, Li W, Kung HJ, Ann DK. HIF-1-alpha links mitochondrial perturbation to the dynamic acquisition of breast cancer tumorigenicity. Oncotarget. 2016 Jun 7;7(23):34052-69. doi: 10.18632/oncotarget.8570. PMID: 27058900; PMCID: PMC5085137. 16: Zhao J, Peng L, Luo Z, Cui R, Yan M. Inhibitory effects of dimethyl α-ketoglutarate in hepatic stellate cell activation. Int J Clin Exp Pathol. 2015 May 1;8(5):5471-7. PMID: 26191252; PMCID: PMC4503123. 17: Hou P, Kuo CY, Cheng CT, Liou JP, Ann DK, Chen Q. Intermediary metabolite precursor dimethyl-2-ketoglutarate stabilizes hypoxia-inducible factor-1α by inhibiting prolyl-4-hydroxylase PHD2. PLoS One. 2014 Nov 24;9(11):e113865. doi: 10.1371/journal.pone.0113865. PMID: 25420025; PMCID: PMC4242664. 18: Mariño G, Pietrocola F, Kong Y, Eisenberg T, Hill JA, Madeo F, Kroemer G. Dimethyl α-ketoglutarate inhibits maladaptive autophagy in pressure overload- induced cardiomyopathy. Autophagy. 2014 May;10(5):930-2. doi: 10.4161/auto.28235. Epub 2014 Mar 20. 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