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SMB00908

Sigma-Aldrich

4-Hydroxy-4-methyl-2-oxoglutaric acid dipotassium salt

95-105% (titration)

Synonym(s):

4-Hydroxy-4-methyl-2-oxoglutaric acid dipotassium salt, Parapyruvate

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About This Item

Linear Formula:
C6H6K2O6
CAS Number:
19071-44-4
Molecular Weight:
252.30
UNSPSC Code:
12352106
NACRES:
NA.25

Assay

95-105% (titration)

form

powder

color

white to beige

solubility

water: soluble 10 mg/mL

General description

Parapyruvate, also known as 4-hydroxy-4-methyl-2-oxoglutarate (HMOG), is a compound formed through the polymerization of two molecules of pyruvate via aldol condensation. It is closely related to α-ketoglutarate and is believed to act as a competitive inhibitor of the α-Ketoglutarate dehydrogenase complex (KGDHC) to form succinyl coenzyme A, impacting fibroblast senescence. A decrease in KGDHC activity is also associated with neurodegenerative disorders such as Alzheimer′s and Parkinson′s diseases. The precise mechanism of parapyruvate′s inhibition of KGDHC is complex, but it interferes with the activity of this rate-limiting enzyme in the tricarboxylic acid (TCA) cycle, ultimately affecting mitochondrial function. KGDHC is crucial for oxidative decarboxylation within the TCA cycle. Parapyruvate′s potential to inhibit KGDHC paves the way for research in cell biology and biochemistry, covering cell senescence, mitochondrial dysfunction, metabolic regulation, and aging-related diseases.

Application

Parapyruvate can be used
  • to study mitochondrial metabolomics
  • to study age related disorders (Alzheimer′s and Parkinson′s research)

Biochem/physiol Actions

Parapyruvate is formed via an adol condensation reaction of pyruvate

Features and Benefits

High quality compound suitable for multiple research applications

Other Notes

For additional information on our range of Biochemicals, please complete this form.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

SMB00908-10MG:
SMB00908-VAR:
SMB00908-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCS4707
0000081412

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Using Taguchi Method to Determine the Optimum Conditions for Synthesizing Parapyruvate
Lee et al.
Molecules (Basel), 27, 1870-1870 (2022)
Parapyruvate, an Impurity in Pyruvate Supplements, Induces Senescence in Human Fibroblastic Hs68 Cells via Inhibition of the ?-Ketoglutarate Dehydrogenase Complex
Chang SC et al.
Journal of Agricultural and Food Chemistry, 66, 7504-7513 (2018)

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