Disodium malonate
[CAS# 141-95-7]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic sodium
• Name: Disodium malonate
• Synonyms: 141-95-7
• Molecular Formula: C₃H₂Na₂O₄
• Molecular Weight: 148.03
• CAS Registry Number: 141-95-7
• EC Number: 205-514-0
• SMILES: C(C(=O)[O-])C(=O)[O-].[Na+].[Na+]

Safety Data

• Safety Statements: S22;S24/25

Discovery and Applications

Disodium malonate, with the chemical formula C3H3Na2O4, is the disodium salt of malonic acid, a dicarboxylic acid. The compound is recognized for its unique chemical properties and versatility in various applications. Disodium malonate is typically produced through the neutralization of malonic acid with sodium hydroxide or sodium carbonate, resulting in a white crystalline powder that is soluble in water.

The discovery of malonate salts, including disodium malonate, traces back to the early 19th century alongside the identification of malonic acid itself. Researchers recognized the potential of malonic acid and its derivatives in organic synthesis, leading to further exploration of their sodium salts.

Disodium malonate has found diverse applications in organic chemistry as a reagent and intermediate in various synthetic processes. One of its primary uses is in the synthesis of other organic compounds, particularly in the malonic ester synthesis. This reaction allows for the formation of malonic esters, which serve as important intermediates in the preparation of α-substituted carboxylic acids. These compounds have significant applications in the pharmaceutical industry, agrochemicals, and materials science.

In addition to its role in organic synthesis, disodium malonate is utilized in biochemistry as a buffering agent. It helps maintain stable pH levels in biochemical reactions and biological processes, making it valuable in laboratories and industrial applications. This property is crucial for experiments involving enzymes and biochemical assays where pH stability is essential for accurate results.

Disodium malonate is also employed in food and beverage applications as a flavoring agent and preservative. Its ability to enhance the flavor profile of various products has led to its inclusion in certain food formulations, contributing to improved taste and shelf life.

In the pharmaceutical industry, disodium malonate has been explored for its potential therapeutic applications. Its derivatives have been investigated for their effectiveness in drug formulations, particularly in enhancing the solubility and bioavailability of certain active pharmaceutical ingredients.

Safety considerations surrounding disodium malonate indicate that it is generally regarded as safe when used in appropriate concentrations. However, like many chemical substances, it should be handled with care to avoid irritation to the skin and eyes.

In conclusion, disodium malonate is a valuable compound in organic synthesis, biochemistry, and food applications. Its discovery and subsequent development underscore its importance in various fields, from pharmaceuticals to laboratory research. The versatility of disodium malonate continues to be explored, highlighting its potential in advancing chemical and biological sciences.

References

2012. Synthesis and evaluation of malonate-based inhibitors of phosphosugar-metabolizing enzymes: Class II fructose-1,6-bis-phosphate aldolases, type I phosphomannose isomerase, and phosphoglucose isomerase. Bioorganic & Medicinal Chemistry, 20(4).
DOI: 10.1016/j.bmc.2011.12.050

2007. The taxonomy of Enterobacter sakazakii: proposal of a new genus Cronobacter gen. nov. and descriptions of Cronobacter sakazakii comb. nov. Cronobacter sakazakii subsp. sakazakii, comb. nov., Cronobacter sakazakii subsp. malonaticus subsp. nov., Cronobacter turicensis sp. nov., Cronobacter muytjensii sp. nov., Cronobacter dublinensis sp. nov. and Cronobacter genomospecies 1. BMC Ecology and Evolution, 7(64).
DOI: 10.1186/1471-2148-7-64

2009. An EPR and optical absorption study of Cu(2+) doped in disodium malonate trihydrate single crystal. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 72(2).
DOI: 10.1016/j.saa.2008.10.004