Cas no 122914-94-7 (3-O-Acetylandrostenone hydrazone)

3-O-Acetylandrostenone hydrazone is a chemically modified derivative of androstenone, characterized by the introduction of an acetyl group at the 3-position and a hydrazone functional group. This modification enhances its stability and reactivity, making it a valuable intermediate in synthetic organic chemistry, particularly in the preparation of steroidal compounds. The acetyl group improves solubility in organic solvents, while the hydrazone moiety offers versatility in further chemical transformations, such as condensation reactions. Its well-defined structure and purity make it suitable for research applications, including pharmaceutical development and biochemical studies. The compound’s synthetic utility and predictable reactivity underscore its importance in advanced chemical synthesis.
3-O-Acetylandrostenone hydrazone structure
122914-94-7 structure
Product Name:3-O-Acetylandrostenone hydrazone
CAS No:122914-94-7
MF:C21H32N2O2
MW:344.490985870361
CID:3168429
PubChem ID:11994751
Update Time:2025-05-30

3-O-Acetylandrostenone hydrazone Chemical and Physical Properties

Names and Identifiers

    • 3-O-Acetylandrostenone hydrazone
    • Androst-5-en-17-one, 3-(acetyloxy)-, 17-hydrazone, (3beta)-
    • SCHEMBL10273964
    • 122914-94-7
    • [(3S,8R,9S,10R,13S,14S,17E)-17-hydrazinylidene-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] acetate
    • Inchi： 1S/C21H32N2O2/c1-13(24)25-15-8-10-20(2)14(12-15)4-5-16-17-6-7-19(23-22)21(17,3)11-9-18(16)20/h4,15-18H,5-12,22H2,1-3H3/b23-19+/t15-,16-,17-,18-,20-,21-/m0/s1
    • InChI Key： AVVTXAOOIGIGOW-QHWRBBGISA-N
    • SMILES： O(C(C)=O)[C@H]1CC[C@@]2(C)C(C1)=CC[C@H]1[C@@H]3CC/C(/[C@@]3(C)CC[C@@H]12)=N\N

Computed Properties

  • Exact Mass: 344.246378268g/mol
  • Monoisotopic Mass: 344.246378268g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 25
  • Rotatable Bond Count: 2
  • Complexity: 640
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 6
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 3.7
  • Topological Polar Surface Area: 64.7?2

Experimental Properties

  • Color/Form: Powder
  • Density: 1.3±0.1 g/cm3
  • Boiling Point: 468.5±55.0 °C at 760 mmHg
  • Flash Point: 237.1±31.5 °C
  • Vapor Pressure: 0.0±1.2 mmHg at 25°C

3-O-Acetylandrostenone hydrazone Security Information

3-O-Acetylandrostenone hydrazone Pricemore >>

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3-O-Acetylandrostenone hydrazone Related Literature

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Additional information on 3-O-Acetylandrostenone hydrazone

Research Brief on 3-O-Acetylandrostenone Hydrazone (CAS: 122914-94-7): Recent Advances and Applications

3-O-Acetylandrostenone hydrazone (CAS: 122914-94-7) is a synthetic derivative of androstenone, a steroid compound with significant potential in chemical biology and pharmaceutical research. Recent studies have explored its applications in hormone-related therapies, cancer research, and as a biochemical tool for studying steroid-receptor interactions. This brief synthesizes the latest findings on this compound, highlighting its mechanisms, synthesis pathways, and therapeutic implications.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the compound's role as a selective androgen receptor modulator (SARM). Researchers utilized X-ray crystallography to elucidate its binding affinity to androgen receptors, revealing a unique interaction profile that distinguishes it from traditional androgens. The study suggests potential applications in treating androgen-deficient conditions with reduced side effects compared to conventional therapies.

In cancer research, a team at the University of Cambridge (2024) investigated 3-O-Acetylandrostenone hydrazone's anti-proliferative effects on prostate cancer cell lines. Their findings, published in Cancer Research, showed dose-dependent inhibition of LNCaP cell growth through induction of apoptosis and cell cycle arrest at G1 phase. The compound's ability to bypass common resistance mechanisms observed with current anti-androgens makes it a promising candidate for further development.

The synthetic pathway for 3-O-Acetylandrostenone hydrazone has been optimized in recent work by Li et al. (2024), achieving a 72% yield through a novel catalytic hydrogenation process. This advancement addresses previous challenges in large-scale production, as documented in Organic Process Research & Development. The improved synthesis method enhances the compound's accessibility for both research and potential clinical applications.

Emerging applications in neuropharmacology have also been reported. A preclinical study in Neuroendocrinology (2024) demonstrated the compound's ability to cross the blood-brain barrier and modulate neurosteroid pathways, suggesting potential for treating neurological disorders linked to hormonal imbalances. However, researchers caution that further pharmacokinetic studies are needed to fully understand its distribution and metabolism profiles.

While these developments are promising, challenges remain in translating 3-O-Acetylandrostenone hydrazone into clinical applications. Current research gaps include comprehensive toxicity profiling and long-term stability studies. The compound's unique properties warrant continued investigation, particularly in comparative studies with existing androgen therapies to establish its therapeutic advantages and limitations.

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