4-Androsten-4-ol-3,17-dione

Base Information

• Chemical Name: 4-Androsten-4-ol-3,17-dione
• CAS No.: 566-48-3
• Molecular Formula: C19H26O3
• Molecular Weight: 302.414
• European Community (EC) Number: 625-331-3
• ChEMBL ID: CHEMBL314699
• Mol file: 566-48-3.mol

Synonyms:4-androsten-4-ol-3,17-dione

Chemical Property of 4-Androsten-4-ol-3,17-dione

Chemical Property:

• Appearance/Colour: Needles
• Vapor Pressure: 9.02E-08mmHg at 25°C
• Melting Point: 199-202 °C
• Refractive Index: 1.545
• Boiling Point: 475.4 °C at 760 mmHg
• PKA: 9.31±0.60(Predicted)
• Flash Point: 255.4 °C
• PSA: 54.37000
• Density: 1.19 g/cm³
• LogP: 3.97310
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 302.18819469
• Heavy Atom Count: 22
• Complexity: 590

Purity/Quality:

99% ^*data from raw suppliers

Formestane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 60
• Safety Statements: 53-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12CCC(=O)C(=C1CCC3C2CCC4(C3CCC4=O)C)O
• Uses: aromatase inhibitors ,it is used for progressive breast cancer. male hormones, assimilating protein class. An antitumor drug. An aromatase inhibitor. An antitumor drug. An aromatase inhibitor antineoplastic, aromatase inhibitor
• production method: Androst-4-ene-3,17-dione (Ⅰ) (1.432g, 5mmo1) is dissolved in 50ml tert-butanol ,add 38mg (0.15mmo1) osmium tetroxide in 2ml t-butanol solution at room temperature, and then 5ml 35% hydrogen peroxide is added, followed by stirring at room temperature for 3 days. After dilution of 100ml brine, and extract with dichloromethane (2 × 100m1). The extract is washed with 100ml brine, , 50ml 10% sodium bisulfite solution, 50ml 10% sodium carbonate solution and 100ml brine, dry over anhydrous sodium sulfate, and concentrate. The residue (1.824g) of the compound (Ⅱ), is dissolved in methanol (10ml),add potassium hydroxide (393mg, 7mmo1) in 3ml methanol . Plus Albert, stirring 10min at 55 ℃. Add 0.3ml of acetic acid and 100ml of brine, and extract with dichloromethane (2 × 100ml). Complex solution, combine, wash with 100ml brine, dry with anhydrous sodium sulfate, and concentrate. The residue (1.727g) by column chromatography on silica gel, wash with hexane-ethyl acetate (7: 3) to give 715mg formestane, yield 47%, mp 200~202 ℃ (acetone).
• Description: 4-hydroxy Androstenedione (4-HAD) is a steroidal inhibitor of aromatase (also known as cytochrome P450 19A1; Ki = 27 nM). As aromatase catalyzes the conversion of androgens to estrogens, aromatase inhibitors, including 4-HAD, are used against hormone-sensitive breast cancer in menopausal women. They are also abused in combination with anabolic steroids in racehorses and athletes. This product is intended for forensic and research applications. Formestane is a potent aromatase inhibitor launched in the UK as a second-line endocrine treatment for breast cancer. As a synthetic derivative of androstanedione, the natural substrate for the biosynthesis of estrogen by the enzyme aromatase, formastane selectively inhibits aromatase and binds to its steroid receptor site to cause a rapid and sustained fall in circulating estrogen level and, therefore, inhibits tumor growth. In patients with existing bulky primary tumors, formestane effectively reduces the size of the tumors. Formastane has apparent tolerability advantages and less side effects than other agents such as aminoglutethimide.

Technology Process of 4-Androsten-4-ol-3,17-dione

There total 29 articles about 4-Androsten-4-ol-3,17-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

4,5-epoxyandrostane-3,17-dione (77057-73-9) → 4-hydroxyandrost-4-ene-3,17-dione (566-48-3)

Guidance literature:

With sulfuric acid; silica gel; acetic acid; at 70 ℃; for 0.05h;

DOI:10.1055/s-2007-985584

Reference yield: 80.0%

3-hydroxy-5α-androst-2-ene-4,17-dione (180303-17-7) → 4-hydroxyandrost-4-ene-3,17-dione (566-48-3)

Guidance literature:

With sodium; In methanol; for 1h; Ambient temperature;

Reference yield: 80.0%

3β,4α-dihydroxy-5β-androstan-17-one (434939-05-6) → 4-hydroxyandrost-4-ene-3,17-dione (566-48-3)

Guidance literature:

3β,4α-dihydroxy-5β-androstan-17-one; With dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In dichloromethane; at -60 ℃; for 3h;

With sodium; In methanol; at 20 ℃; for 3h;

DOI:10.1016/S0039-128X(01)00164-7

upstream raw materials:

Androstenedione

4ξ,5-dihydroxy-5ξ-androstane-3,17-dione

acetic acid

4,5-epoxyandrostane-3,17-dione

Downstream raw materials:

4-acetoxyandrostenedione

4-(O-acetylsalicyloxy)-5β-androst-3-en-17-one

4-(O-acetylsalicyloxy)-5α-androst-3-en-17-one

4-(O-acetylsalicyloxy)androst-4-en-3,17-dione

Refernces

• 1、 Martin, Glenroy D. A.,Narvaez, Javier,Marti, Anne. "Synthesis and bioconversions of formestane". . p. 1966 - 1969. Retrieved 2013.
• 2、 Zhu, Rui,Xing, Lixin,Wang, Xinyan,Cheng, Chuanjie,Liu, Bo,Hu, Yuefei. "Practical preparation of diosphenols by ring opening of α,β-epoxyketones catalyzed by silica gel supported acids". . p. 2267 - 2271. Retrieved 2008/02/09.