2691-68-1

Basic information

• Product Name: 3-hydroxyandrosta-5,7-dien-17-one
• Synonyms: 3-hydroxyandrosta-5,7-dien-17-one
• CAS NO: 2691-68-1
• Molecular Formula: C₁₉H₂₆O₂
• Molecular Weight: 286.4085
• Mol File: 2691-68-1.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 448.4°Cat760mmHg
• Flash Point: 191°C
• Appearance: /
• Density: 1.14g/cm³
• Vapor Pressure: 6.36E-10mmHg at 25°C
• Refractive Index: 1.578
• CAS DataBase Reference: 3-hydroxyandrosta-5,7-dien-17-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxyandrosta-5,7-dien-17-one(2691-68-1)
• EPA Substance Registry System: 3-hydroxyandrosta-5,7-dien-17-one(2691-68-1)

Safety Data

• Hazardous Substances Data: 2691-68-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C19H26O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3-4,13,15-16,20H,5-11H2,1-2H3/t13?,15-,16-,18-,19-/m0/s1

Upstream product

• 64110-61-8 (3β)-3-Acetoxyandrosta-5,7-dien-17-one 
• 146863-67-4 Acetic acid (3S,8R,9S,10R,13S,14S)-7-bromo-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 53-43-0 dehydroepiandrosterone 
• 81968-78-7 3β-hydroxy-5,7-pregnadien-20-one 
• 1177400-16-6 3β-tert-butyldimethylsilyloxy-7α-chloroandrost-5-en-17-one 
• 23668-18-0 7α-bromo-3β-(acetyloxy)androst-5-en-17-one 
• 853-23-6 prasterone acetate 

Downstream Products

• 4675-73-4 androsta-4,7-diene-3,17-dione 
• 157522-95-7 (3β,5Z,7E)-9,10-Secocholesta-5,7,10(19),16-tetraen-23-yne-3,25-diol diacetate 

Relevant articles and documents

Design, synthesis and biological evaluation of novel 5α, 8α-endoperoxide steroidal derivatives with hybrid side chain as anticancer agents

A series of novel 5α, 8α-endoperoxide steroidal hybrid derivatives containing isatin or indole substituents on the C-17 side chain were synthesized and characterized. The preliminary anti-proliferative activity of the compounds against HepG2, MCF-7, HT-29 and HeLa cell lines were investigated. Compounds 7g and 7l displayed significant anti-proliferative activity in vitro against HepG2 and Hela cells, with IC50 values lower than 8 μM. Furthermore, the biological functions of 7g were examined by flow cytometry and colony analysis. The results showed that 7g could induce HepG2 cell apoptosis, inhibited cell cycle progression, and colony growth. The studies indicated that structural modification at C-17 position could be a promising launch point for design steroidal anticancer agents.

Synthesis and Biological Evaluation of Novel Steroidal 5α,8α-Endoperoxide Derivatives with Aromatic Hydrazone Side Chain as Potential Anticancer Agents

Abstract: Seven new steroidal 5α,8α-endoperoxide derivatives with C-17 aromatic hydrazone side chain were synthesized. Structures of the synthesized compounds were characterized by IR, 1H NMR, 13C NMR, and mass spectrometry. Anti-proliferative activities of the synthesized compounds were evaluated in vitro by the MTT method. Among the seven compounds, 5α,8α-epidioxy-17-(4-chloro-benzylidene)-hydrazonoandrost-3β-ol showed the strongest anti-proliferative activity against three human cancer cell lines (MCF-7, HepG2, and SK-Hep1).

Synthesis and biological evaluation of novel steroidal 5α,8α-epidioxyandrost-6-ene-3β-ol-17-(O-phenylacetamide)oxime derivatives as potential anticancer agents

Inspired by the significant anti-cancer activity of our previously screened natural ergosterol peroxide (EP, 1), we synthesized and characterized a series of novel 5α,8α-epidioxyandrost-3β-ol-17-(O-phenylacetamide)oxime derivatives (9a–o). The anti-proliferative activity of the synthesized compounds against human hepatocellular carcinoma cells (HepG2, Sk-Hep1) and human breast cancer cells (MCF-7, MDA-MB231) were investigated. Compounds 9d, 9f, 9h, 9j and 9m displayed good anti-proliferative activity (most IC50??20?μM) in vitro. Furthermore, fluorescence imaging showed that the designed coumarin-9d conjugate (12) localized mainly in mitochondria, leading to enhanced anticancer activities over the parent structure.

3beta-hydroxy-5alpha, 8alpha-peroxoandrost-6-en-17-(arring substituted) hydrazone derivative and preparation and application thereof

The invention discloses a 3beta-hydroxy-5alpha, 8alpha -Peroxyandrost-6-en-17-(aromatic ring substituted) hydrazone derivative, preparation and application thereof, and belongs to the technical fieldof medicine chemistry. The structural formula of the 3beta-hydroxy-5alpha, 8alpha -Peroxyandrost-6-en-17-(aromatic ring substituted) hydrazone derivative is shown in the description, wherein R1 represents -CH3, -F, -Cl, -C(CH3)3, -CN, -OCH3, -OH or -H; R2 represents -OC, -H3, -CF3, or -H. Dehydroepiandrosterone is used as the starting material to prepare 3beta -Acetoxy-5-Androstene-17-ketones, followed by bromination and debromination to obtain 3beta-Hydroxyl-5alpha, 8alpha -Peroxyandrost-6-en-17-a hydrazine intermediate , hydrolysis to reduce hydroxyl groups, and then the light is constructed by 5alpha, 8alpha- peroxy bridge which then reacts with hydrazine hydrate to obtain 3beta-Hydroxyl-5alpha, 8alpha -Peroxyandrost-6-en-17-a hydrazine intermediate, and then reacted with hydrazine hydrate to obtain 3beta-Hydroxyl-5alpha, 8alpha -Peroxyandrost-6-en-17-a hydrazine intermediate, and finally the aldehyde amine condensation reaction is carried out to generate 3beta-hydroxyl-5alpha, 8alpha -Peroxyandrost-6-ene-17-(aromatic ring substituted) hydrazone derivatives. The compound has the effects of preventing and treating cancers such as liver cancer, breast cancer and the like.