Cas no 5223-99-4 (3α-Acetoxyandrost-5-en-17-one)
3α-Acetoxyandrost-5-en-17-one Chemical and Physical Properties
Names and Identifiers
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- Androst-5-en-17-one,3-(acetyloxy)-, (3a)-
- DEHYDROANDROSTERONE ACETATE
- DEHYDROEPIANDROSTERONE ACETATE,
- benzoic acid, 3-[(1-oxopropyl)amino]-, methyl ester
- Methyl 3-(propionylamino)benzoate
- 3α-Acetoxyandrost-5-en-17-one
-
- Inchi: 1S/C21H30O3/c1-13(22)24-15-8-10-20(2)14(12-15)4-5-16-17-6-7-19(23)21(17,3)11-9-18(16)20/h4,15-18H,5-12H2,1-3H3/t15-,16-,17-,18-,20-,21-/m0/s1
- InChI Key: NCMZQTLCXHGLOK-ZKHIMWLXSA-N
- SMILES: [C@]12([H])CC[C@]3(C)C(CC[C@@]3([H])[C@]1([H])CC=C1C[C@@H](OC(=O)C)CC[C@]21C)=O
Computed Properties
- Exact Mass: 207.08959
- Monoisotopic Mass: 207.089543
- Isotope Atom Count: 0
- Hydrogen Bond Donor Count: 1
- Hydrogen Bond Acceptor Count: 3
- Heavy Atom Count: 15
- Rotatable Bond Count: 4
- Complexity: 240
- 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: 1.9
- Topological Polar Surface Area: 55.4
Experimental Properties
- Density: 1.171
- Boiling Point: 387.4°C at 760 mmHg
- Flash Point: 188.1°C
- Refractive Index: 1.556
- PSA: 55.4
3α-Acetoxyandrost-5-en-17-one Pricemore >>
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| TRC | A522390-5mg |
3α-Acetoxyandrost-5-en-17-one |
5223-99-4 | 5mg |
$ 170.00 | 2022-06-08 | ||
| TRC | A522390-25mg |
3α-Acetoxyandrost-5-en-17-one |
5223-99-4 | 25mg |
$ 790.00 | 2022-06-08 | ||
| TRC | A522390-50mg |
3α-Acetoxyandrost-5-en-17-one |
5223-99-4 | 50mg |
$ 1360.00 | 2022-06-08 |
3α-Acetoxyandrost-5-en-17-one Related Literature
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Kanjun Sun,Fengting Hua,Shuzhen Cui,Yanrong Zhu,Hui Peng,Guofu Ma RSC Adv., 2021,11, 37631-37642
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Yang Chen,Di Zhou,Zheyi Meng,Jin Zhai Chem. Commun., 2016,52, 10020-10023
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Jianyao Huang,Dong Gao,Zhihui Chen,Weifeng Zhang Polym. Chem., 2021,12, 2471-2480
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Mark D. Allendorf,Alauddin Ahmed,Tom Autrey,Jeffrey Camp,Eun Seon Cho,Maciej Haranczyk,Abhi Karkamkar,Di-Jia Liu,Katie R. Meihaus,Iffat H. Nayyar,Roman Nazarov,Donald J. Siegel,Vitalie Stavila,Jeffrey J. Urban,Srimukh Prasad Veccham,Brandon C. Wood Energy Environ. Sci., 2018,11, 2784-2812
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Govind Reddy Mol. Syst. Des. Eng., 2021,6, 779-789
Additional information on 3α-Acetoxyandrost-5-en-17-one
Introduction to 3α-Acetoxyandrost-5-en-17-one (CAS No. 5223-99-4)
3α-Acetoxyandrost-5-en-17-one, identified by its Chemical Abstracts Service (CAS) number 5223-99-4, is a significant compound in the field of biochemistry and pharmacology. This steroidal derivative belongs to the class of androgens, specifically featuring an acetoxy group at the 3α-position and a ketone at the 17β-position. Its structural configuration makes it a valuable intermediate in synthetic chemistry and a subject of interest in medical research due to its potential biological activities.
The compound’s molecular formula, C??H??O?, reflects its steroidal backbone with modifications that influence its pharmacokinetic and pharmacodynamic properties. The presence of the 3α-acetoxy group enhances its solubility in polar solvents, making it more amenable for formulation in pharmaceutical applications. Additionally, the 17-one ketone moiety is a common feature in androgenic compounds, suggesting possible interactions with androgen receptors.
Recent studies have highlighted the role of 3α-Acetoxyandrost-5-en-17-one in investigating the mechanisms of steroid hormone action. Researchers have been particularly interested in its potential as a prodrug or modulator of androgen receptor activity. For instance, modifications to this scaffold have been explored to develop selective androgen receptor modulators (SARMs), which aim to provide therapeutic benefits with reduced side effects compared to traditional androgens.
In vitro studies have demonstrated that 3α-Acetoxyandrost-5-en-17-one can exhibit agonistic properties at certain steroid receptors, though its binding affinity and selectivity vary depending on the assay conditions. These findings are crucial for understanding how structural changes in steroidal compounds can modulate receptor interactions, providing insights into designing next-generation therapeutics.
The compound has also been studied for its potential role in metabolic disorders. Emerging research suggests that steroidal derivatives like 3α-Acetoxyandrost-5-en-17-one may influence lipid metabolism and glucose homeostasis. This has sparked interest in exploring its application in treating metabolic syndromes, including obesity and type 2 diabetes. The acetoxy group at the 3α-position appears to play a key role in these metabolic effects, possibly by interacting with peroxisome proliferator-activated receptors (PPARs).
From a synthetic chemistry perspective, 3α-Acetoxyandrost-5-en-17-one serves as a versatile building block for constructing more complex steroidal molecules. Its availability as a reference compound allows chemists to develop novel derivatives with tailored biological activities. Techniques such as semi-synthetic modification or total synthesis have been employed to produce analogs that may exhibit improved pharmacological profiles.
The pharmaceutical industry has taken note of 3α-Acetoxyandrost-5-en-17-one due to its potential therapeutic applications. Preclinical trials have been conducted to evaluate its efficacy and safety in animal models, focusing on conditions such as muscle wasting, osteoporosis, and benign prostatic hyperplasia (BPH). While these studies are still in progress, they underscore the growing interest in exploring non-androgenic steroidal compounds as alternatives to existing treatments.
Advances in analytical techniques have also enhanced our understanding of 3α-Acetoxyandrost-5-en-17-one’s behavior in biological systems. Mass spectrometry, nuclear magnetic resonance (NMR) spectroscopy, and high-performance liquid chromatography (HPLC) are routinely used to characterize the compound’s metabolites and interactions with biological targets. These tools provide critical data for optimizing drug design and improving drug delivery systems.
The regulatory landscape for 3α-Acetoxyandrost-5-en-17-one is evolving alongside advancements in medical research. Regulatory agencies require comprehensive toxicological assessments before approving new steroidal drugs for clinical use. This ensures that compounds like 3α-Acetoxyandrost-5-en-17-one are safe for human consumption while maximizing therapeutic benefits.
In conclusion, 3α-Acetoxyandrost-5-en-17-one (CAS No. 5223-99-4) represents a promising area of research with significant implications for biochemistry and medicine. Its unique structural features make it a valuable tool for studying steroid hormone mechanisms, developing SARMs, and addressing metabolic disorders. As research continues to uncover new applications for this compound, it is likely to remain a cornerstone of steroidal drug development.
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