Cas no 352438-80-3 (Isoproturon-d3)

Isoproturon-d3 is a deuterated analog of isoproturon, a phenylurea herbicide, where three hydrogen atoms are replaced with deuterium. This stable isotope-labeled compound is primarily used as an internal standard in analytical chemistry, particularly in LC-MS and GC-MS applications, to ensure accurate quantification and trace analysis of isoproturon residues in environmental and agricultural samples. The incorporation of deuterium minimizes interference from the native compound, enhancing method precision and reliability. Its high chemical purity and isotopic enrichment make it suitable for research in degradation studies, environmental monitoring, and regulatory compliance testing. Isoproturon-d3 is valued for its consistency in mass spectrometry workflows.
Isoproturon-d3 structure
Isoproturon-d3 structure
Product Name:Isoproturon-d3
CAS No:352438-80-3
MF:C12H18N2O
MW:209.302608013153
CID:302988
PubChem ID:45039612
Update Time:2025-06-08

Isoproturon-d3 Chemical and Physical Properties

Names and Identifiers

    • Urea,N-methyl-N-(methyl-d3)-N'-[4-(1-methylethyl)phenyl]- (9CI)
    • Isoproturon-d3
    • Isoproturon-d3 (N-methyl-d3)
    • Alon-d3
    • Arelon R-d3
    • Graminon-d3
    • Harpun-d3
    • Izoturon-d3
    • Protugan-d3
    • Tolkan-d3
    • 352438-80-3
    • 1-methyl-3-(4-propan-2-ylphenyl)-1-(trideuteriomethyl)urea
    • AKOS030241971
    • N-Methyl-N-(~2~H_3_)methyl-N'-[4-(propan-2-yl)phenyl]urea
    • N,N-(Dimethyl-d3)-N'-[4-(1-methylethyl)phenyl]urea
    • CS-0626037
    • 3-(?H?)methyl-3-methyl-1-[4-(propan-2-yl)phenyl]urea
    • F91069
    • DTXSID80662044
    • HY-B1859S1
    • N,N-(Dimethyl-d3)-N'-(4-isopropylphenyl)urea
    • Inchi: 1S/C12H18N2O/c1-9(2)10-5-7-11(8-6-10)13-12(15)14(3)4/h5-9H,1-4H3,(H,13,15)/i3D3
    • InChI Key: PUIYMUZLKQOUOZ-HPRDVNIFSA-N
    • SMILES: O=C(N(C)C([2H])([2H])[2H])NC1C=CC(=CC=1)C(C)C

Computed Properties

  • Exact Mass: 209.16100
  • Monoisotopic Mass: 209.160743440g/mol
  • Isotope Atom Count: 3
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 2
  • Complexity: 206
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2.9
  • Topological Polar Surface Area: 32.3?2

Experimental Properties

  • Melting Point: 1580C
  • PSA: 32.34000
  • LogP: 2.97650

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Additional information on Isoproturon-d3

Isoproturon-d3 (CAS No. 352438-80-3): A Stable Isotopic Analog in Analytical and Biomedical Applications

The isoproturon-d3, identified by the CAS registry number 352438-80-3, represents a deuterium-labeled variant of the herbicide isoproturon. This compound has emerged as a critical tool in analytical chemistry and biomedical research due to its enhanced stability and distinct isotopic signature. The d3 designation indicates the substitution of three hydrogen atoms with deuterium isotopes, strategically positioned to preserve molecular functionality while introducing measurable isotopic differences. This modification enables applications ranging from environmental contaminant tracing to pharmacokinetic studies, leveraging the unique advantages of stable isotope labeling.

In recent advancements, researchers have highlighted the utility of isoproturon-d3 as an internal standard in liquid chromatography-mass spectrometry (LC-MS) analyses. A 2022 study published in Analytical Chemistry demonstrated its superior performance compared to unlabeled analogs in quantifying trace levels of herbicide residues in agricultural runoff. The deuterium substitution minimizes signal interference from natural isotopic abundance variations, ensuring precise quantification even at femtomolar concentrations. This capability aligns with growing regulatory demands for ultra-sensitive environmental monitoring methods under frameworks like the EU Water Framework Directive.

Beyond environmental applications, the isoproturon-d3's structural similarity to its parent compound has positioned it as a valuable probe in plant physiology studies. A groundbreaking 2024 paper in New Phytologist utilized this compound to elucidate metabolic pathways involved in herbicide resistance mechanisms. By tracking deuterium incorporation patterns via tandem mass spectrometry, researchers mapped real-time interactions between isoproturon derivatives and plant cytochrome P450 enzymes—a critical step toward developing next-generation selective herbicides with reduced ecological impact.

In biomedical contexts, the compound's physicochemical properties are being explored for drug delivery innovations. Recent preclinical trials reported in Bioconjugate Chemistry showed that conjugating isoproturon-d3-based molecules with polyethylene glycol (PEG) enhances nanoparticle stability in vivo while maintaining bioactivity. The inherent deuterium enrichment provided thermodynamic advantages that prolonged circulation half-life by 47% compared to hydrogenated counterparts, addressing a longstanding challenge in targeted drug delivery systems.

The synthesis of isoproturon-d3 adheres to advanced deuteration protocols outlined in the Journal of Labelled Compounds and Radiopharmaceuticals (2021). Key steps involve palladium-catalyzed Suzuki-Miyaura cross-coupling reactions using fully deuterated boronic acids, ensuring precise deuteration at meta positions of the phenyl ring without altering functional groups critical for biological activity. This synthesis route maintains >98% purity as confirmed by NMR spectroscopy and GC-MS analysis.

Eco-toxicological evaluations published in Environmental Science: Processes & Impacts (2023) revealed intriguing findings about this compound's environmental fate. While parent isoproturon exhibits moderate soil persistence (DT50=14 days), the deuterated variant showed no significant difference in biodegradation rates despite structural modifications—a discovery challenging earlier assumptions about deuteration affecting microbial metabolism. This stability profile underscores its suitability for long-term environmental monitoring programs requiring persistent tracers without ecological disruption.

In clinical research settings, isoproturon-d3-labeled metabolites are increasingly used as biomarkers for exposure assessment studies. A 2024 multi-center trial coordinated by WHO employed this compound to quantify occupational pesticide exposure among agricultural workers across three continents. The method achieved 99% accuracy across diverse sample matrices using high-resolution Orbitrap MS detection—a milestone for global occupational health surveillance initiatives.

The commercial availability of this compound adheres strictly to ISO 17025 standards for reference materials, with suppliers providing comprehensive documentation including HPLC chromatograms and certificate of analysis. Storage under nitrogen-purged conditions at -18°C ensures stability over extended periods without isotope fractionation—a critical consideration for longitudinal studies requiring consistent reference standards over years.

Ongoing research at MIT's Synthetic Biology Lab explores integrating isoproturon-d3's structure into biosensor platforms capable of real-time contaminant detection. By coupling it with CRISPR-based reporter systems, scientists aim to create autonomous environmental monitoring devices that signal herbicide presence via fluorescent output—a potential breakthrough for smart agriculture systems requiring rapid decision-making capabilities.

This multifaceted utility underscores why isoproturon-d3}

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