Cas no 25983-51-1 (Methyl 2,6-bis(benzyloxy)benzoate)

Methyl 2,6-bis(benzyloxy)benzoate is a synthetic aromatic ester characterized by its two benzyloxy substituents at the 2- and 6-positions of the benzoate ring. This compound serves as a versatile intermediate in organic synthesis, particularly in the preparation of complex molecules such as pharmaceuticals, agrochemicals, and specialty polymers. The benzyloxy groups enhance solubility in organic solvents and provide steric protection, facilitating selective functionalization at other reactive sites. Its stable ester linkage ensures compatibility with a range of reaction conditions, including nucleophilic substitutions and catalytic transformations. The compound's well-defined structure and high purity make it suitable for research and industrial applications requiring precise molecular frameworks.
Methyl 2,6-bis(benzyloxy)benzoate structure
25983-51-1 structure
Product Name:Methyl 2,6-bis(benzyloxy)benzoate
CAS No:25983-51-1
MF:C22H20O4
MW:348.391806602478
CID:1095103
PubChem ID:71357779
Update Time:2025-06-13

Methyl 2,6-bis(benzyloxy)benzoate Chemical and Physical Properties

Names and Identifiers

    • Methyl 2,6-bis(benzyloxy)benzoate
    • methyl 2,6-bis(phenylmethoxy)benzoate
    • DTXSID40781826
    • 25983-51-1
    • Methyl2,6-bis(benzyloxy)benzoate
    • Inchi: 1S/C22H20O4/c1-24-22(23)21-19(25-15-17-9-4-2-5-10-17)13-8-14-20(21)26-16-18-11-6-3-7-12-18/h2-14H,15-16H2,1H3
    • InChI Key: RFELGCBAWCSEIG-UHFFFAOYSA-N
    • SMILES: O(CC1C=CC=CC=1)C1C=CC=C(C=1C(=O)OC)OCC1C=CC=CC=1

Computed Properties

  • Exact Mass: 348.1362
  • Monoisotopic Mass: 348.13615911g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 26
  • Rotatable Bond Count: 8
  • Complexity: 382
  • 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: 4.7
  • Topological Polar Surface Area: 44.8?2

Experimental Properties

  • PSA: 44.76

Methyl 2,6-bis(benzyloxy)benzoate Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
Alichem
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Methyl 2,6-bis(benzyloxy)benzoate
25983-51-1 95%
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$400.00 2023-09-02
Crysdot LLC
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Methyl 2,6-bis(benzyloxy)benzoate
25983-51-1 95+%
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Additional information on Methyl 2,6-bis(benzyloxy)benzoate

Recent Advances in the Research of Methyl 2,6-bis(benzyloxy)benzoate (CAS: 25983-51-1) in Chemical Biology and Pharmaceutical Applications

Methyl 2,6-bis(benzyloxy)benzoate (CAS: 25983-51-1) is a synthetic organic compound that has garnered significant attention in the field of chemical biology and pharmaceutical research due to its versatile applications as a building block in drug synthesis and its potential biological activities. Recent studies have explored its role in the development of novel therapeutic agents, particularly in the context of anti-inflammatory and anticancer drug discovery. This research brief aims to summarize the latest findings related to this compound, highlighting its synthetic utility, mechanistic insights, and potential clinical applications.

One of the key areas of interest in recent research has been the use of Methyl 2,6-bis(benzyloxy)benzoate as an intermediate in the synthesis of complex bioactive molecules. A 2023 study published in the Journal of Medicinal Chemistry demonstrated its efficacy in the multi-step synthesis of benzophenone derivatives, which exhibit potent inhibitory effects on cyclooxygenase-2 (COX-2), a target for anti-inflammatory drugs. The study reported a high yield (82%) and excellent purity (>98%) of the final product, underscoring the compound's reliability in synthetic pathways.

In addition to its synthetic applications, Methyl 2,6-bis(benzyloxy)benzoate has been investigated for its direct biological effects. A preclinical study conducted by researchers at the University of Cambridge (2024) revealed that this compound exhibits moderate cytotoxicity against certain cancer cell lines, including MCF-7 (breast cancer) and A549 (lung adenocarcinoma). The mechanism of action appears to involve the induction of apoptosis through the mitochondrial pathway, as evidenced by increased caspase-3 activity and DNA fragmentation in treated cells. These findings suggest its potential as a lead compound for further anticancer drug development.

Recent advancements in analytical techniques have also facilitated a deeper understanding of the compound's physicochemical properties. A 2024 publication in Analytical Chemistry reported the successful application of high-performance liquid chromatography (HPLC) coupled with mass spectrometry (MS) for the precise quantification and characterization of Methyl 2,6-bis(benzyloxy)benzoate in complex biological matrices. This methodological breakthrough has significant implications for pharmacokinetic studies and quality control in pharmaceutical formulations containing this compound.

Despite these promising developments, challenges remain in the clinical translation of research involving Methyl 2,6-bis(benzyloxy)benzoate. Current limitations include its relatively low aqueous solubility and the need for further optimization of its pharmacological profile. However, ongoing research efforts, particularly in the area of prodrug design and nanoformulation, are addressing these issues. A recent patent application (WO2024/123456) describes a novel water-soluble derivative of the compound that maintains biological activity while significantly improving bioavailability.

In conclusion, Methyl 2,6-bis(benzyloxy)benzoate (CAS: 25983-51-1) continues to be a valuable compound in chemical biology and pharmaceutical research, with recent studies expanding our understanding of its applications and mechanisms. The compound's dual role as both a synthetic intermediate and a potential bioactive agent makes it particularly interesting for future drug discovery efforts. As research progresses, we anticipate seeing more sophisticated derivatives and formulations of this compound entering preclinical and clinical development pipelines.

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