Cas no 19536-25-5 (2-O-Acetyl-20-hydroxyecdysone)

2-O-Acetyl-20-hydroxyecdysone is a bioactive ecdysteroid derivative, structurally related to 20-hydroxyecdysone with an acetyl group at the 2-position. This modification enhances its lipophilicity, potentially improving membrane permeability and bioavailability compared to its parent compound. It exhibits notable anabolic and adaptogenic properties, making it valuable in research on metabolic regulation, muscle growth, and stress response. The acetyl group also increases stability, reducing susceptibility to enzymatic degradation. Its precise mechanism involves interaction with ecdysone receptors, influencing gene expression related to growth and development. This compound is particularly useful in pharmacological and biochemical studies, offering a refined tool for investigating ecdysteroid signaling pathways.
2-O-Acetyl-20-hydroxyecdysone structure
2-O-Acetyl-20-hydroxyecdysone structure
Product Name:2-O-Acetyl-20-hydroxyecdysone
CAS No:19536-25-5
MF:C29H46O8
MW:522.670750141144
CID:2032543
Update Time:2025-06-23

2-O-Acetyl-20-hydroxyecdysone Chemical and Physical Properties

Names and Identifiers

    • 20-hydroxyecdysone, 2-acetate
    • ECDYSONE-2-ACETATE, BETA-(AS)
    • ECDYSONE-2-ACETATE, BETA-(SH)
    • 2-O-Acetyl-20-hydroxyecdysone
    • (2beta,3beta,5beta,22R)-2-(Acetyloxy)-3,14,20,22,25-pentahydroxycholest-7-en-6-one
    • beta-Ecdysone 2-acetate
    • 20-hydroxyeedysone 2-acetate
    • Inchi: 1S/C29H46O8/c1-16(30)37-22-15-26(4)17-7-11-27(5)23(28(6,35)24(33)9-10-25(2,3)34)8-12-29(27,36)18(17)13-20(31)19(26)14-21(22)32/h13,17,19,21-24,32-36H,7-12,14-15H2,1-6H3/t17-,19-,21+,22-,23-,24+,26+,27+,28+,29+/m0/s1
    • InChI Key: TXLUXHSVMYTTCI-FORVDKSSSA-N
    • SMILES: O[C@@]12CC[C@H]([C@](C)([C@@H](CCC(C)(C)O)O)O)[C@@]1(C)CC[C@H]1C2=CC([C@@H]2C[C@H]([C@H](C[C@]12C)OC(C)=O)O)=O

Computed Properties

  • Exact Mass: 522.31926842 g/mol
  • Monoisotopic Mass: 522.31926842 g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 5
  • Hydrogen Bond Acceptor Count: 8
  • Heavy Atom Count: 37
  • Rotatable Bond Count: 7
  • Complexity: 975
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 10
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Molecular Weight: 522.7
  • XLogP3: 1
  • Topological Polar Surface Area: 145?2

Experimental Properties

  • Color/Form: Powder
  • Density: 1.26±0.1 g/cm3 (20 oC 760 Torr),
  • Melting Point: 218-220 oC
  • Solubility: Very slightly soluble (0.24 g/l) (25 o C),

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Additional information on 2-O-Acetyl-20-hydroxyecdysone

2-O-Acetyl-20-hydroxyecdysone: A Comprehensive Overview

2-O-Acetyl-20-hydroxyecdysone (CAS No. 19536-25-5) is a naturally occurring compound belonging to the class of ecdysteroids, which are steroidal hormones playing a crucial role in the development and growth of arthropods, particularly insects. This compound is a derivative of ecdysone, a key molting hormone that regulates metamorphosis in insects. The 2-O-Acetyl modification adds a unique functional group to the molecule, potentially influencing its biological activity and pharmacokinetics.

Recent studies have highlighted the importance of ecdysteroids in various biological processes, including cell proliferation, apoptosis, and immune regulation. 2-O-Acetyl-20-hydroxyecdysone has been shown to exhibit diverse bioactivities, making it a subject of interest in both basic research and applied sciences. For instance, researchers have explored its potential as a lead compound for developing novel insecticides or growth regulators in agriculture.

The molecular structure of 2-O-Acetyl-20-hydroxyecdysone consists of a steroidal backbone with hydroxyl and acetyl groups at specific positions. This structural arrangement contributes to its ability to interact with ecdysteroid receptors (EcRs), which are critical for its biological functions. Recent advancements in computational chemistry have allowed scientists to model the binding interactions between this compound and EcRs, providing insights into its mechanism of action.

One of the most promising applications of 2-O-Acetyl-20-hydroxyecdysone lies in its potential as a biopesticide. Traditional chemical pesticides often pose environmental risks and contribute to pesticide resistance in target insects. In contrast, ecdysteroids like this compound offer a more sustainable approach by targeting specific developmental stages of insects without harming non-target species. Field trials have demonstrated that formulations containing ecdysteroids can effectively disrupt insect life cycles, reducing crop damage without adverse environmental impacts.

Another area of active research is the exploration of ecdysteroids as therapeutic agents. Preclinical studies suggest that these compounds may possess anti-inflammatory and anti-cancer properties. For example, 2-O-Acetyl-20-hydroxyecdysone has been shown to inhibit the proliferation of certain cancer cell lines by modulating signaling pathways involved in cell cycle regulation. While these findings are preliminary, they underscore the potential for further development into clinical applications.

The synthesis and purification of 2-O-Acetyl-20-hydroxyecdysone have also been subjects of recent investigations. Traditional extraction methods from natural sources, such as insect larvae or plant tissues, are often labor-intensive and yield limited quantities. To address this, chemists have developed efficient synthetic routes using advanced organic chemistry techniques. These methods not only enhance the scalability of production but also allow for the creation of analogs with improved bioactivity or stability.

In conclusion, 2-O-Acetyl-20-hydroxyecdysone (CAS No. 19536-25-5) is a versatile compound with significant potential across multiple fields. Its role as an ecdysteroid makes it invaluable for understanding insect biology and developing sustainable agricultural solutions. Furthermore, its emerging therapeutic applications highlight the need for continued research into its mechanisms and clinical relevance. As scientific advancements continue to unfold, this compound is poised to play an increasingly important role in both basic science and applied technologies.

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