Cas no 135683-73-7 (Kauran-3-one, 16,17-dihydroxy-, (16alpha)-)

Kauran-3-one, 16,17-dihydroxy-, (16alpha)- structure
135683-73-7 structure
Product Name:Kauran-3-one, 16,17-dihydroxy-, (16alpha)-
CAS No:135683-73-7
MF:C20H32O3
MW:320.466286659241
CID:152818
PubChem ID:392471
Update Time:2025-07-15

Kauran-3-one, 16,17-dihydroxy-, (16alpha)- Chemical and Physical Properties

Names and Identifiers

    • Kauran-3-one, 16,17-dihydroxy-, (16alpha)-
    • 16-EPIABBEOKUTONE
    • abbeokutone
    • ENT-3-OXOKAURANE-16,17-DIOL
    • ent-3-Oxokaurane-16α
    • [ "ent-3-Oxokaurane-16α", "17-diol" ]
    • NSC 692967
    • ent-16(S),17-Dihydroxykauran-3-one
    • hydroxy-(hydroxymethyl)-trimethyl-[?]one
    • 16,17-dihydroxykauran-3-one
    • CS-0017245
    • HY-N1596
    • Kauran-3-one, 16,17-dihydroxy-, (16.alpha.)-
    • ent-3-Oxokaurane-16,17-dio
    • AKOS032948580
    • NSC692967
    • NSC-692967
    • 135683-73-7
    • (1S,4S,9S,10R,13R,14S)-14-hydroxy-14-(hydroxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.01,10.04,9]hexadecan-6-one
    • ent-16S,17-Dihydroxykauran-3-one
    • Ent-16
    • A,17-dihydroxykauran-3-one
    • 1H-2,10a-Ethanophenanthrene, kauran-3-one deriv.; 16-Epiabbeokutone; 3-Oxo-ent-kaurane-16,17-diol; Ent-16,17-dihydroxykauran-3-one
    • DTXSID20929108
    • (1S,4S,9S,10R,13R,14S)-14-HYDROXY-14-(HYDROXYMETHYL)-5,5,9-TRIMETHYLTETRACYCLO[11.2.1.0(1),(1)?.0?,?]HEXADECAN-6-ONE
    • 14-hydroxy-14-(hydroxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.01,10.04,9]hexadecan-6-one
    • DA-59882
    • Inchi: 1S/C20H32O3/c1-17(2)14-6-9-19-10-13(20(23,11-19)12-21)4-5-15(19)18(14,3)8-7-16(17)22/h13-15,21,23H,4-12H2,1-3H3/t13-,14-,15+,18-,19+,20-/m1/s1
    • InChI Key: MPDUJZZNNBJFAB-XYYNDNLRSA-N
    • SMILES: O[C@@]1(CO)C[C@@]23CC[C@@H]4C(C)(C)C(CC[C@@]4(C)[C@@H]2CC[C@@H]1C3)=O

Computed Properties

  • Exact Mass: 320.23514488g/mol
  • Monoisotopic Mass: 320.23514488g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 23
  • Rotatable Bond Count: 1
  • Complexity: 541
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 6
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 3
  • Topological Polar Surface Area: 57.5?2

Experimental Properties

  • Color/Form: Powder

Kauran-3-one, 16,17-dihydroxy-, (16alpha)- Security Information

Kauran-3-one, 16,17-dihydroxy-, (16alpha)- Pricemore >>

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Additional information on Kauran-3-one, 16,17-dihydroxy-, (16alpha)-

Recent Advances in the Study of Kauran-3-one, 16,17-dihydroxy-, (16alpha)- (CAS: 135683-73-7) in Chemical Biology and Pharmaceutical Research

Kauran-3-one, 16,17-dihydroxy-, (16alpha)- (CAS: 135683-73-7) is a diterpenoid compound that has garnered significant attention in recent years due to its potential therapeutic applications. This compound, belonging to the kaurane family, exhibits a unique structural framework characterized by a 16,17-dihydroxy configuration and a 3-one functional group. Recent studies have explored its pharmacological properties, including anti-inflammatory, anti-cancer, and neuroprotective effects, making it a promising candidate for drug development.

One of the most notable advancements in the study of Kauran-3-one, 16,17-dihydroxy-, (16alpha)- is its role in modulating inflammatory pathways. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that this compound effectively inhibits the NF-κB signaling pathway, a key regulator of inflammation. The study utilized in vitro models of macrophage activation and in vivo models of acute inflammation, revealing a dose-dependent reduction in pro-inflammatory cytokines such as TNF-α and IL-6. These findings suggest potential applications in treating chronic inflammatory diseases like rheumatoid arthritis and inflammatory bowel disease.

In the realm of oncology, Kauran-3-one, 16,17-dihydroxy-, (16alpha)- has shown promising anti-cancer activity. Research published in Cancer Research (2024) highlighted its ability to induce apoptosis in various cancer cell lines, including breast, lung, and colon cancer. The compound was found to activate the intrinsic apoptotic pathway by upregulating pro-apoptotic proteins like Bax and downregulating anti-apoptotic proteins such as Bcl-2. Additionally, it exhibited synergistic effects when combined with conventional chemotherapeutic agents, suggesting its potential as an adjunct therapy in cancer treatment.

Another area of interest is the neuroprotective potential of Kauran-3-one, 16,17-dihydroxy-, (16alpha)-. A recent study in Neuropharmacology (2024) investigated its effects on oxidative stress and neuronal apoptosis in models of neurodegenerative diseases. The compound was shown to scavenge reactive oxygen species (ROS) and enhance the activity of endogenous antioxidant enzymes, such as superoxide dismutase (SOD) and catalase. These effects were accompanied by a reduction in neuronal apoptosis, indicating its potential utility in treating conditions like Alzheimer's and Parkinson's diseases.

The synthesis and structural modification of Kauran-3-one, 16,17-dihydroxy-, (16alpha)- have also been a focus of recent research. A 2024 study in Organic & Biomolecular Chemistry reported a novel synthetic route for this compound, improving yield and scalability. The study also explored the structure-activity relationship (SAR) by introducing various functional groups at the C-3 and C-16 positions, leading to derivatives with enhanced pharmacological activity. These advancements are critical for the development of more potent and selective analogs for clinical applications.

Despite these promising findings, challenges remain in the clinical translation of Kauran-3-one, 16,17-dihydroxy-, (16alpha)-. Issues such as bioavailability, metabolic stability, and potential toxicity need to be addressed through further preclinical and clinical studies. However, the growing body of evidence underscores its potential as a multifaceted therapeutic agent, warranting continued investigation.

In conclusion, Kauran-3-one, 16,17-dihydroxy-, (16alpha)- (CAS: 135683-73-7) represents a versatile compound with significant therapeutic potential across various disease areas. Recent studies have elucidated its mechanisms of action, optimized its synthesis, and explored its applications in inflammation, cancer, and neurodegeneration. As research progresses, this compound may pave the way for novel treatment strategies in the chemical biology and pharmaceutical fields.

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