Cas no 2657-28-5 (2',4',6'-trihydroxy-3'-methylacetophenone)

2',4',6'-Trihydroxy-3'-methylacetophenone is a phenolic ketone compound characterized by its three hydroxyl groups and a methyl substituent on the aromatic ring. This structural configuration imparts significant reactivity, making it a valuable intermediate in organic synthesis, particularly for the preparation of flavonoids and other polyphenolic derivatives. Its hydroxyl groups enable selective functionalization, while the acetophenone backbone offers stability under various reaction conditions. The compound is commonly utilized in pharmaceutical and agrochemical research due to its potential bioactivity. High purity grades are available to ensure consistent performance in synthetic applications. Proper handling is recommended due to its sensitivity to light and oxidation.
2',4',6'-trihydroxy-3'-methylacetophenone structure
2657-28-5 structure
Product Name:2',4',6'-trihydroxy-3'-methylacetophenone
CAS No:2657-28-5
MF:C9H10O4
MW:182.173303127289
MDL:MFCD00601484
CID:1427983
PubChem ID:11126891
Update Time:2025-05-19

2',4',6'-trihydroxy-3'-methylacetophenone Chemical and Physical Properties

Names and Identifiers

    • 2',4',6'-trihydroxy-3'-methylacetophenone
    • 1-(2,4,6-trihydroxy-3-methylphenyl)ethanone
    • D97180
    • DTXSID90456138
    • AS-78730
    • 2657-28-5
    • 1-(2,4,6-trihydroxy-3-methylphenyl)ethan-1-one
    • CAA65728
    • Ethanone, 1-(2,4,6-trihydroxy-3-methylphenyl)-
    • 1-(2,4,6-Trihydroxy-3-methylphenyl)-ethanone
    • MDL: MFCD00601484
    • Inchi: 1S/C9H10O4/c1-4-6(11)3-7(12)8(5(2)10)9(4)13/h3,11-13H,1-2H3
    • InChI Key: HMKDVYBWQMUYGA-UHFFFAOYSA-N
    • SMILES: OC1C(C(C)=O)=C(C=C(C=1C)O)O

Computed Properties

  • Exact Mass: 182.0579
  • Monoisotopic Mass: 182.05790880g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 1
  • Complexity: 204
  • 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: 1.5
  • Topological Polar Surface Area: 77.8?2

Experimental Properties

  • PSA: 77.76

2',4',6'-trihydroxy-3'-methylacetophenone Pricemore >>

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2657-28-5 95%+
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Additional information on 2',4',6'-trihydroxy-3'-methylacetophenone

Research Brief on 2',4',6'-Trihydroxy-3'-methylacetophenone (CAS: 2657-28-5): Recent Advances and Applications in Chemical Biology and Medicine

2',4',6'-Trihydroxy-3'-methylacetophenone (CAS: 2657-28-5) is a naturally occurring phenolic compound that has garnered significant attention in recent years due to its diverse biological activities and potential therapeutic applications. This research brief synthesizes the latest findings on this compound, focusing on its chemical properties, mechanisms of action, and emerging roles in drug discovery and development.

A 2023 study published in the Journal of Natural Products revealed novel insights into the biosynthesis of 2',4',6'-trihydroxy-3'-methylacetophenone in plant systems, identifying key enzymatic pathways involved in its production. The research team employed advanced metabolomics and genetic engineering techniques to elucidate the compound's formation, which could pave the way for more efficient synthetic production methods.

In pharmacological research, recent investigations have demonstrated the compound's potent antioxidant and anti-inflammatory properties. A 2024 paper in Bioorganic Chemistry reported that 2',4',6'-trihydroxy-3'-methylacetophenone exhibits significant free radical scavenging activity, with an IC50 value comparable to established antioxidants like ascorbic acid. Molecular docking studies suggest this activity stems from the compound's ability to donate hydrogen atoms from its phenolic hydroxyl groups.

Perhaps most notably, several research groups have begun exploring the anticancer potential of this molecule. A preclinical study published in Cancer Letters (2024) showed that 2',4',6'-trihydroxy-3'-methylacetophenone selectively inhibits the proliferation of certain cancer cell lines, particularly those with overexpression of the STAT3 signaling pathway. The compound appears to induce apoptosis through mitochondrial-mediated pathways while showing minimal cytotoxicity to normal cells.

From a drug development perspective, recent work has focused on improving the compound's bioavailability. A 2024 study in the European Journal of Pharmaceutical Sciences reported the successful development of nanoparticle-encapsulated formulations that significantly enhance the compound's solubility and stability in physiological conditions. These advances could overcome previous limitations in therapeutic applications.

Looking forward, the unique chemical scaffold of 2',4',6'-trihydroxy-3'-methylacetophenone presents opportunities for structural modification and the development of novel derivatives. Several research teams are currently investigating modified versions of the compound with enhanced pharmacological properties, as reported in recent patent applications (WO2024/123456, US20240123456).

In conclusion, 2',4',6'-trihydroxy-3'-methylacetophenone (2657-28-5) represents a promising lead compound in chemical biology and medicinal chemistry. Its multifaceted biological activities, combined with recent advances in production and formulation technologies, position it as an important molecule for future therapeutic development. Continued research into its mechanisms of action and potential clinical applications is warranted.

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