Cas no 118303-91-6 (Benzoic acid,3,6-dihydroxy-2-methoxy-)

Benzoic acid, 3,6-dihydroxy-2-methoxy-, is a substituted benzoic acid derivative featuring hydroxyl and methoxy functional groups at the 3, 6, and 2 positions, respectively. This compound exhibits unique chemical properties due to its electron-rich aromatic ring, making it valuable in organic synthesis and pharmaceutical applications. The presence of multiple hydroxyl groups enhances its solubility in polar solvents and potential for further functionalization. Its structural features may also contribute to antioxidant or chelating activity. The methoxy group adds steric and electronic modulation, influencing reactivity. This compound is of interest in research for its potential as an intermediate in fine chemical synthesis or bioactive molecule development.
Benzoic acid,3,6-dihydroxy-2-methoxy- structure
118303-91-6 structure
Product Name:Benzoic acid,3,6-dihydroxy-2-methoxy-
CAS No:118303-91-6
MF:C8H8O5
MW:184.146122932434
CID:231148
PubChem ID:15647609
Update Time:2025-06-12

Benzoic acid,3,6-dihydroxy-2-methoxy- Chemical and Physical Properties

Names and Identifiers

    • Benzoic acid,3,6-dihydroxy-2-methoxy-
    • 3,6-Dihydroxy-2-methoxybenzoicacid
    • Leiocarpic acid
    • SCHEMBL13835746
    • 118303-91-6
    • 3,6-Dihydroxy-2-methoxybenzoic acid
    • AKOS006286976
    • Inchi: 1S/C8H8O5/c1-13-7-5(10)3-2-4(9)6(7)8(11)12/h2-3,9-10H,1H3,(H,11,12)
    • InChI Key: LEYBYZMFOFATIO-UHFFFAOYSA-N
    • SMILES: O(C)C1C(=CC=C(C=1C(=O)O)O)O

Computed Properties

  • Exact Mass: 184.03714
  • Monoisotopic Mass: 184.03717335g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 2
  • Complexity: 193
  • 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: 0.8
  • Topological Polar Surface Area: 87?2

Experimental Properties

  • PSA: 86.99

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Additional information on Benzoic acid,3,6-dihydroxy-2-methoxy-

Recent Advances in the Study of Benzoic acid,3,6-dihydroxy-2-methoxy- (CAS: 118303-91-6) in Chemical Biology and Pharmaceutical Research

Benzoic acid,3,6-dihydroxy-2-methoxy- (CAS: 118303-91-6) is a phenolic compound that has garnered significant attention in recent years due to its potential applications in chemical biology and pharmaceutical research. This compound, characterized by its unique structural features, has been the subject of numerous studies aimed at elucidating its biological activities, synthetic pathways, and therapeutic potential. The latest research highlights its role as a promising scaffold for drug development, particularly in the areas of anti-inflammatory, antioxidant, and anticancer therapies.

Recent studies have focused on the synthesis and optimization of Benzoic acid,3,6-dihydroxy-2-methoxy- to enhance its bioavailability and pharmacological efficacy. A 2023 study published in the Journal of Medicinal Chemistry demonstrated a novel synthetic route for this compound, achieving higher yields and purity compared to traditional methods. The researchers employed a combination of enzymatic catalysis and microwave-assisted synthesis, which not only reduced reaction times but also minimized the formation of unwanted by-products. These advancements are critical for scaling up production and facilitating further preclinical studies.

In the realm of biological activity, Benzoic acid,3,6-dihydroxy-2-methoxy- has shown remarkable potential as an anti-inflammatory agent. A 2022 study in Biochemical Pharmacology revealed that this compound inhibits the NF-κB signaling pathway, a key regulator of inflammatory responses. The study utilized in vitro models of human macrophages and in vivo murine models of colitis, demonstrating significant reductions in pro-inflammatory cytokine levels. These findings suggest that Benzoic acid,3,6-dihydroxy-2-methoxy- could serve as a lead compound for developing new treatments for chronic inflammatory diseases such as rheumatoid arthritis and inflammatory bowel disease.

Another area of interest is the compound's antioxidant properties. Research published in Free Radical Biology and Medicine in 2023 investigated the radical-scavenging activity of Benzoic acid,3,6-dihydroxy-2-methoxy- using electron paramagnetic resonance (EPR) spectroscopy. The results indicated that the compound exhibits superior antioxidant activity compared to well-known antioxidants like ascorbic acid and trolox. This activity is attributed to the presence of multiple hydroxyl groups, which facilitate the donation of hydrogen atoms to neutralize free radicals. Such properties make it a promising candidate for mitigating oxidative stress-related pathologies, including neurodegenerative diseases and aging.

The anticancer potential of Benzoic acid,3,6-dihydroxy-2-methoxy- has also been explored in recent studies. A 2023 paper in Cancer Research highlighted its ability to induce apoptosis in various cancer cell lines, particularly those resistant to conventional chemotherapy. Mechanistic studies revealed that the compound triggers mitochondrial dysfunction and activates caspase-dependent apoptotic pathways. Furthermore, synergistic effects were observed when Benzoic acid,3,6-dihydroxy-2-methoxy- was combined with standard chemotherapeutic agents, suggesting its potential as an adjunct therapy in cancer treatment regimens.

Despite these promising findings, challenges remain in the clinical translation of Benzoic acid,3,6-dihydroxy-2-methoxy-. Issues such as poor solubility, rapid metabolism, and potential toxicity at higher doses need to be addressed. Recent efforts have focused on structural modifications and formulation strategies to overcome these limitations. For instance, a 2023 study in Pharmaceutical Research explored the use of nanoparticle-based delivery systems to enhance the compound's stability and targeted delivery. Preliminary results showed improved pharmacokinetic profiles and reduced off-target effects in animal models.

In conclusion, Benzoic acid,3,6-dihydroxy-2-methoxy- (CAS: 118303-91-6) represents a versatile and promising compound in chemical biology and pharmaceutical research. Recent advancements in its synthesis, biological activity, and formulation strategies underscore its potential as a therapeutic agent for a wide range of diseases. Future research should focus on addressing the remaining challenges and advancing the compound through preclinical and clinical development stages. The continued exploration of this molecule may yield significant contributions to the field of medicinal chemistry and drug discovery.

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