Cas no 6622-76-0 (Methyl tiglate)

Methyl tiglate (methyl (E)-2-methyl-2-butenoate) is an unsaturated ester characterized by its fruity, apple-like aroma. It is commonly used as a flavor and fragrance intermediate in the food, beverage, and cosmetic industries. The compound exhibits high purity and stability, making it suitable for precise formulations. Its distinct chemical structure, featuring a conjugated double bond system, allows for reactivity in organic synthesis, particularly in Michael additions and Diels-Alder reactions. Methyl tiglate is also valued for its low toxicity and compatibility with a range of solvents, enhancing its versatility in industrial applications. Proper handling requires standard ester precautions, including storage in cool, dry conditions away from strong oxidizers.
Methyl tiglate structure
Methyl tiglate structure
Product Name:Methyl tiglate
CAS No:6622-76-0
MF:C6H10O2
MW:114.142402172089
MDL:MFCD00016654
CID:46885
PubChem ID:5323652
Update Time:2025-06-14

Methyl tiglate Chemical and Physical Properties

Names and Identifiers

    • Methyl tiglate
    • Methyl 2-methylcrotonate
    • 2-Carbomethoxy-2-bute
    • 2-methyl-but-2-enoic acid methyl ester
    • dimethylacrylic acid methyl ester
    • Methyl-2-methylcrotonat
    • methylalpha-methylcrotonate
    • Tiglic acid methyl
    • TIGLIC ACID METHYL ESTER
    • MDL: MFCD00016654
    • Inchi: 1S/C6H10O2/c1-4-5(2)6(7)8-3/h4H,1-3H3/b5-4-
    • InChI Key: YYJWBYNQJLBIGS-PLNGDYQASA-N
    • SMILES: COC(/C(=C\C)/C)=O
    • BRN: 1720455

Computed Properties

  • Exact Mass: 114.06800

Experimental Properties

  • Density: 0.95
  • Melting Point: 37.22°C (estimate)
  • Boiling Point: 139°C
  • Flash Point: 35 oC
  • Refractive Index: 1.435-1.437
  • Water Partition Coefficient: Soluble in alcohol, water 3813 mg/L @ 25°C (est).
  • Stability/Shelf Life: Stable. Flammable. Incompatible with strong oxidising agents.
  • PSA: 26.30000
  • LogP: 1.12560
  • Merck: 14,9433

Methyl tiglate Security Information

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Additional information on Methyl tiglate

Recent Advances in Methyl Tiglate (CAS 6622-76-0) Research: Applications and Innovations in Chemical Biology and Pharmaceuticals

Methyl tiglate (CAS 6622-76-0), an ester derived from tiglic acid, has garnered significant attention in recent years due to its versatile applications in chemical biology and pharmaceutical research. This compound, characterized by its fruity odor and structural simplicity, serves as a key intermediate in the synthesis of bioactive molecules and flavoring agents. Recent studies have explored its potential in drug discovery, fragrance formulation, and as a building block for more complex chemical entities. This research brief synthesizes the latest findings on methyl tiglate, focusing on its chemical properties, biological activities, and emerging applications in the pharmaceutical and biotechnology sectors.

A 2023 study published in the Journal of Medicinal Chemistry highlighted the role of methyl tiglate as a precursor in the synthesis of novel anti-inflammatory agents. Researchers utilized its α,β-unsaturated ester moiety to develop a series of derivatives with potent cyclooxygenase-2 (COX-2) inhibitory activity. The study reported a 40% improvement in selectivity for COX-2 over COX-1 compared to traditional NSAIDs, suggesting its potential as a scaffold for safer anti-inflammatory drugs. Molecular docking simulations further revealed that methyl tiglate derivatives interact favorably with the COX-2 active site, providing a structural basis for future drug design.

In the realm of agrochemicals, methyl tiglate has shown promise as a bioactive component. A 2024 Nature Chemical Biology publication demonstrated its effectiveness as a semiochemical in pest management strategies. Field trials conducted with methyl tiglate-based formulations exhibited a 65% reduction in pest infestation compared to control groups, while maintaining low environmental toxicity. The compound's volatility and structural stability make it particularly suitable for slow-release formulations, addressing a critical need in sustainable agriculture.

Recent advances in biocatalysis have expanded the production methods for methyl tiglate. A team at MIT developed an engineered E. coli strain capable of producing methyl tiglate from renewable feedstocks with 92% yield, as reported in ACS Synthetic Biology (2024). This green chemistry approach not only improves sustainability but also reduces production costs by 30% compared to traditional chemical synthesis routes. The biocatalytic process demonstrates excellent stereoselectivity, producing enantiomerically pure methyl tiglate, which is crucial for pharmaceutical applications.

The fragrance industry has also benefited from innovations involving methyl tiglate. A 2023 patent (US20230183621A1) describes novel microencapsulation techniques that enhance the longevity of methyl tiglate in personal care products. These advancements address the compound's historical challenges with volatility while preserving its desirable organoleptic properties. Market analysis indicates a projected 7.2% CAGR for methyl tiglate in fragrance applications between 2024 and 2030, driven by increasing demand for natural-inspired scent profiles.

Emerging research in chemical biology suggests potential therapeutic applications for methyl tiglate beyond its traditional uses. Preliminary studies indicate its ability to modulate certain G-protein coupled receptors (GPCRs) involved in metabolic regulation. While these findings require further validation, they open new avenues for investigating methyl tiglate derivatives in metabolic disorder therapeutics. The compound's favorable pharmacokinetic properties, including good oral bioavailability and moderate plasma half-life, make it an attractive candidate for further medicinal chemistry exploration.

Quality control and analytical methods for methyl tiglate have seen significant improvements. A 2024 Journal of Pharmaceutical and Biomedical Analysis article presented a validated GC-MS method capable of detecting methyl tiglate at concentrations as low as 0.1 ppm with 99.8% accuracy. This advancement supports the compound's use in pharmaceutical formulations where precise quantification is essential. The method has been successfully applied to stability studies, confirming methyl tiglate's robustness under various storage conditions.

In conclusion, methyl tiglate (CAS 6622-76-0) continues to demonstrate remarkable versatility across multiple scientific disciplines. From its established role in fragrance chemistry to emerging applications in drug discovery and sustainable agriculture, this compound represents a valuable asset in chemical biology research. Future studies should focus on expanding its therapeutic potential, optimizing production methods, and exploring novel derivatives with enhanced biological activities. The cumulative evidence positions methyl tiglate as a compound of significant interest for both academic researchers and industrial applications in the coming years.

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