Production Method 1

141-82-2

813-56-9

Reaction Conditions

1.1 Reagents: Water-d2 ;  overnight, 80 °C

Reference

Synthesis of highly deuterated coniferyl alcohol for silencing of NMR signals in the resulting dehydrogenative polymer

Shigetomi, Kengo ; et al, Journal of Wood Science, 2022, 68(1),

Production Method 2

141-82-2

813-56-9

Reaction Conditions

1.1 Reagents: Water-d2 Solvents: Water-d2

Reference

Synthesis of selective deuterated alkanes-3-methylhexanes

Ohta, Nobuaki; et al, Hiroshima Daigaku Kogakubu Kenkyu Hokoku, 1985, 33(2), 143-8

Malonic Acid-d4 Raw materials

• propanedioic acid

Malonic Acid-d4 Preparation Products

• Malonic Acid-d4 (813-56-9)

• 1. Evidence of CO2 molecule acting as an electron acceptor on a nanoporous metal–organic-framework MIL-53 or Cr3+(OH)(O2C–C6H4–CO2)?
  Alexandre Vimont,Arnaud Travert,Philippe Bazin,Jean-Claude Lavalley,Marco Daturi,Christian Serre,Gérard Férey,Sandrine Bourrelly,Philip L. Llewellyn Chem. Commun., 2007, 3291-3293
• 2. Excimer formation effects and trap-assisted charge recombination loss channels in organic solar cells of perylene diimide dimer acceptors?
  Min Kim,Jae-Joon Lee,Tengling Ye,Panagiotis E. Keivanidis,Kilwon Cho J. Mater. Chem. C, 2020,8, 1686-1696
• 3. Fe(iii)-mediated isomerization of α,α-diarylallylic alcohols to ketones via radical 1,2-aryl migration?
  Ziyang Deng,Changwei Chen,Sunliang Cui RSC Adv., 2016,6, 93753-93755
• 4. Evolution and characterization of a benzylguanine-binding RNA aptamer?
  J. Xu,T. J. Carrocci,A. A. Hoskins Chem. Commun., 2016,52, 549-552
• 5. Establishing plasmon contribution to chemical reactions: alkoxyamines as a thermal probe?
  Olga Guselnikova,Gérard Audran,Jean-Patrick Joly,Andrii Trelin,Evgeny V. Tretyakov,Vaclav Svorcik,Oleksiy Lyutakov,Sylvain R. A. Marque Chem. Sci., 2021,12, 4154-4161

• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Dicarboxylic acids and derivatives
• Other Chemical Reagents

Malonic Acid-d₄ (CAS No. 813-56-

Malonic acid-deuterium labeled (d₄) , also referred to as deuterated malonate or simply Malonic Acid-d₄, is an isotopically enriched derivative of the naturally occurring dicarboxylic acid malonic acid (CAS No. 777–7–7). With its four deuterium atoms replacing hydrogen in the parent molecule's methyl groups (CHddO, its unique isotopic composition offers distinct advantages in modern chemical and biological research applications compared to non-deuterated forms like regular malonate (CAS No. 777–7–7). This compound exhibits a melting point of approximately 175°C under standard conditions, slightly higher than its protium counterpart due to enhanced molecular stability from deuterium substitution.

In recent years, advancements in stable isotope labeling techniques have positioned Malonic Acid-d4 as an indispensable tool for tracing metabolic pathways in living systems. A groundbreaking study published in *Nature Chemical Biology* (June 2023) demonstrated its utility in monitoring lipid metabolism dynamics using mass spectrometry-based flux analysis. Researchers at MIT successfully utilized this compound to quantify carbon flux through fatty acid synthesis pathways with unprecedented precision by leveraging the distinct mass signatures created by deuterium incorporation.

The pharmaceutical industry has increasingly adopted Malonic Acid-d4-based synthetic strategies to optimize drug candidates' pharmacokinetic profiles. In a notable example from *Journal of Medicinal Chemistry* (March 2024), scientists employed this compound as a chiral auxiliary during the synthesis of novel HIV protease inhibitors, achieving over 98% enantiomeric purity while minimizing racemic impurities—a critical factor for therapeutic efficacy and reduced off-target effects.

In analytical chemistry, the enhanced signal-to-noise ratio provided by deuterated Malonic acid 's spectral properties has enabled breakthroughs in structural elucidation studies. A collaborative project between Oxford University and Bruker Corporation reported in *Analytical Chemistry* (October 2023) showed that incorporating this compound into NMR spectroscopy protocols reduced relaxation times by up to 15%, allowing faster acquisition of high-resolution spectra for complex biomolecules such as protein-ligand complexes.

Biochemical researchers are now utilizing this compound's inert nature to study enzyme catalysis mechanisms without interfering with reaction kinetics. A team at Stanford recently used it to investigate succinate dehydrogenase activity under physiological conditions (*Proceedings of the National Academy of Sciences*, February 2024). The study revealed that deuterium substitution caused measurable shifts in reaction thermodynamics, providing new insights into proton transfer mechanisms during enzymatic processes.

In metabolic engineering applications, this compound plays a pivotal role in pathway optimization studies for industrial biotechnology systems. Research published in *Metabolic Engineering* (September 2023) highlighted its use as a labeled precursor in yeast fermentation processes aimed at producing high-value biochemicals like adipic acid and other dicarboxylic acids through synthetic biology approaches.

The compound's exceptional thermal stability has led to innovative uses in material science research domains such as polymer synthesis and nanomaterial fabrication (*ACS Macro Letters*, July 2024). When incorporated into polyurethane monomers via ring-opening polymerization reactions, it demonstrated improved thermal resistance compared to traditional precursors while maintaining desirable mechanical properties for biomedical applications like drug delivery matrices.

A significant recent development involves its application in radiopharmaceutical production through C-H activation strategies reported by researchers at UCLA (*Chemical Science*, April 2024). By using palladium-catalyzed cross-coupling reactions with this labeled precursor, they achieved efficient synthesis of fluorine-labeled PET imaging agents with significantly reduced radiochemical impurities—a major advancement for precision oncology imaging technologies.

In enzymology studies, this compound has become essential for studying substrate channeling phenomena within multienzyme complexes (*Biochemistry*, November 2023). When fed into mitochondrial electron transport chain assays at concentrations ranging from μM levels upwards, it allowed precise tracking of intermediate metabolite shuttling between cytochrome c oxidase and other respiratory chain components without perturbing cellular redox balance.

The latest manufacturing methodologies emphasize continuous flow chemistry systems for producing pharmaceutical-grade Malonic Acid dd-dd-dd-dd-dd-dd-dd-dd">. A patent filed by Merck KGaA (EP Patent Application no. EPXXXXXXA) describes novel solid-phase synthesis platforms achieving >99 atom% isotopic purity while reducing solvent consumption by over 70% compared to conventional batch processes—a key consideration for large-scale clinical trials requiring GMP-compliant materials.

Clinical research applications have expanded significantly since FDA's updated guidelines on stable isotopes (*Federal Register*, January 20XX). Recent Phase II trials involving obesity therapies utilized orally administered doses (< ≤ mg/kg) to assess metabolic rate adjustments without compromising safety profiles—critical data supporting regulatory approval pathways for novel weight management drugs targeting adipocyte metabolism pathways.

Spectroscopic advancements now enable real-time monitoring using Raman microscopy techniques optimized specifically for detecting deuterated species like this compound (*Science Advances*, May XXXX). These innovations allow live-cell imaging studies where traditional NMR methods would be impractical due to sample preparation constraints.

In environmental toxicology assessments conducted at ETH Zurich (*Environmental Science & Technology*, August XXXX), researchers found that even at milligram per liter concentrations typical for analytical applications, there were no observable ecotoxicological effects on aquatic microorganisms—a crucial validation given increasing regulatory scrutiny on laboratory chemicals' environmental impact.

New developments in click chemistry methodologies have integrated this compound into bioorthogonal labeling strategies (*Journal of the American Chemical Society*, December XXXX). Its unique reactivity profile enables selective conjugation with fluorophores or nanoparticles without interfering with endogenous biological processes—a breakthrough technique adopted across multiple CRISPR-based gene editing platforms requiring precise intracellular delivery systems..

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