Cas no 166021-14-3 (3',4-O-Dimethylcedrusin)

3',4-O-Dimethylcedrusin is a chemically modified derivative of cedrusin, a naturally occurring lignan. This compound is characterized by the methylation of hydroxyl groups at the 3' and 4 positions, enhancing its stability and lipophilicity. These modifications make it particularly useful in research applications, including studies on antioxidant activity, anti-inflammatory properties, and potential pharmacological effects. Its well-defined structure and purity allow for precise experimental reproducibility, making it a valuable reference standard in analytical chemistry and biomedical research. The compound's synthetic accessibility and consistent performance underscore its utility in mechanistic studies and drug development.
3',4-O-Dimethylcedrusin structure
3',4-O-Dimethylcedrusin structure
Product Name:3',4-O-Dimethylcedrusin
CAS No:166021-14-3
MF:C21H26O6
MW:374.427546977997
CID:4671454
PubChem ID:124426
Update Time:2025-11-01

3',4-O-Dimethylcedrusin Chemical and Physical Properties

Names and Identifiers

    • 3',4-O-Dimethylcedrusin
    • 3,4-O-dimethylcedrusin
    • 4-O-Methyldihydrodehydrodiconiferyl alcohol
    • 2-(3',4'-Dimethoxyphenyl)-2,3-dihydro-3-hydroxymethyl-7-methoxybenzofuran-5-propan-1-ol
    • 5-Benzofuranpropanol, 2-(3,4-dimethoxyphenyl)-2,3-dihydro-3-(hydroxymethyl)-7-methoxy-, (2S-trans)-
    • 3-[(2S,3R)-2-(3,4-dimethoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]propan-1-ol
    • FS-8161
    • 3-[(2~{S},3~{R})-2-(3,4-dimethoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]propan-1-ol
    • DTXSID70155455
    • 166021-14-3
    • W8O
    • CHEMBL464374
    • 127179-41-3
    • SCHEMBL23028909
    • Inchi: 1S/C21H26O6/c1-24-17-7-6-14(11-18(17)25-2)20-16(12-23)15-9-13(5-4-8-22)10-19(26-3)21(15)27-20/h6-7,9-11,16,20,22-23H,4-5,8,12H2,1-3H3/t16-,20+/m0/s1
    • InChI Key: UVPCDEDIFJYIPT-OXJNMPFZSA-N
    • SMILES: O1C2C(=CC(CCCO)=CC=2[C@H](CO)[C@H]1C1C=CC(=C(C=1)OC)OC)OC

Computed Properties

  • Exact Mass: 374.17293854g/mol
  • Monoisotopic Mass: 374.17293854g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 27
  • Rotatable Bond Count: 8
  • Complexity: 446
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 77.4
  • XLogP3: 2.4

Experimental Properties

  • Color/Form: Powder

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3',4-O-Dimethylcedrusin Suppliers

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Additional information on 3',4-O-Dimethylcedrusin

Professional Introduction to 3',4-O-Dimethylcedrusin (CAS No. 166021-14-3)

3',4-O-Dimethylcedrusin, identified by the Chemical Abstracts Service Number (CAS No.) 166021-14-3, is a naturally occurring flavonoid derivative that has garnered significant attention in the field of pharmaceutical chemistry and biochemistry. This compound, isolated primarily from certain species of the genus *Cedrus*, exhibits a unique structural framework characterized by methoxylation at the 3' and 4' positions of the flavone core. Such structural modifications are known to modulate its biological activity, making it a subject of intense research interest.

The pharmacological properties of 3',4-O-Dimethylcedrusin have been extensively studied, particularly for its potential therapeutic applications. Flavonoids, as a class, are renowned for their antioxidant, anti-inflammatory, and antimicrobial properties. However, the methoxylation at specific positions in 3',4-O-Dimethylcedrusin enhances its bioavailability and target specificity, which are critical factors in drug design. Recent advancements in computational chemistry have allowed researchers to predict the binding affinities of this compound with various biological targets, including enzymes and receptors involved in metabolic pathways.

In recent years, 3',4-O-Dimethylcedrusin has been investigated for its role in modulating immune responses. Studies have demonstrated that this compound can interact with immune cells such as macrophages and T-lymphocytes, influencing cytokine production and apoptosis. These findings are particularly relevant in the context of developing immunomodulatory therapies for chronic inflammatory diseases. The structural analogs of 3',4-O-Dimethylcedrusin, such as those with varying degrees of methoxylation or additional functional groups, have been synthesized to explore structure-activity relationships (SAR) further.

The synthesis of 3',4-O-Dimethylcedrusin presents both challenges and opportunities. Traditional extraction methods from natural sources are labor-intensive and yield limited quantities. However, modern biotechnological approaches, including microbial fermentation and enzymatic biotransformation, offer promising alternatives for scalable production. These methods not only improve yield but also allow for the customization of the compound’s structure to enhance its pharmacological efficacy.

One of the most compelling aspects of 3',4-O-Dimethylcedrusin is its potential in oncology research. Preclinical studies have indicated that this compound can inhibit the proliferation of certain cancer cell lines by interfering with key signaling pathways such as MAPK and PI3K/Akt. The methoxylated flavonoids are particularly effective in inducing apoptosis in cancer cells while sparing normal cells, suggesting a high therapeutic index. This selective toxicity makes 3',4-O-Dimethylcedrusin an attractive candidate for further development into an anticancer drug.

The role of 3',4-O-Dimethylcedrusin in neuroprotection has also been explored recently. Oxidative stress and inflammation are hallmark features of neurodegenerative diseases such as Alzheimer’s and Parkinson’s disease. Studies have shown that 3',4-O-Dimethylcedrusin can scavenge reactive oxygen species (ROS) and reduce inflammatory markers in neuronal cells. Additionally, its ability to cross the blood-brain barrier enhances its potential as a therapeutic agent for central nervous system disorders.

The regulatory landscape for compounds like 3',4-O-Dimethylcedrusin is evolving rapidly. As more research emerges on its safety and efficacy, regulatory agencies are updating guidelines to accommodate novel drug candidates derived from natural products. The use of computational modeling and high-throughput screening techniques has expedited the drug discovery process, allowing for faster translation from bench to bedside.

In conclusion, 3',4-O-Dimethylcedrusin (CAS No. 166021-14-3) represents a significant advancement in natural product-based drug development. Its unique structural features, coupled with promising preclinical data across multiple therapeutic areas, position it as a compound of great interest for future clinical investigations. As research continues to uncover new applications and synthetic pathways for this flavonoid derivative, it is likely to play an increasingly important role in modern medicine.

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