64110-61-8

Basic information

• Product Name: 17-oxoandrosta-5,7-dien-3-yl acetate
• CAS NO: 64110-61-8
• Molecular Formula: C₂₁H₂₈O₃
• Molecular Weight: 328.4452
• Mol File: 64110-61-8.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 453.3°C at 760 mmHg
• Flash Point: 197.4°C
• Density: 1.14g/cm³
• Vapor Pressure: 2.09E-08mmHg at 25°C
• Refractive Index: 1.555
• CAS DataBase Reference: 17-oxoandrosta-5,7-dien-3-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 17-oxoandrosta-5,7-dien-3-yl acetate(64110-61-8)
• EPA Substance Registry System: 17-oxoandrosta-5,7-dien-3-yl acetate(64110-61-8)

Safety Data

• Hazardous Substances Data: 64110-61-8(Hazardous Substances Data)

Usage

Chemical class

Steroid derivatives

Parent compound

Androstenone

Biological function

Potent pheromone

Source

Boars and other mammalian species

Characteristic odor

Responsible for the odor associated with boars

Application

Used in the formulation of synthetic pheromones

Target species

Sows

Behavioral effect

Attracts and stimulates reproductive behaviors

Potential use

Animal husbandry and agriculture

Purpose

Controlling mating behavior and reproductive efficiency
These properties and specific content provide a comprehensive overview of 17-oxoandrosta-5,7-dien-3-yl acetate, highlighting its chemical nature, biological function, and potential applications in various fields.

Upstream product

• 23668-18-0 7α-bromo-3β-(acetyloxy)androst-5-en-17-one 
• 124853-32-3 androsta-5,7-diene-3β,17β-diol 3-acetate 
• 53-43-0 dehydroepiandrosterone 
• 853-23-6 prasterone acetate 
• 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 

Downstream Products

• 2691-68-1 3β-hydroxyandrosta-5,7-diene-17-one 
• 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

Biogenesis-Guided Synthesis and Structural Revision of Sarocladione Enabled by Ruthenium-Catalyzed Endoperoxide Fragmentation

Sarocladione is the first 5,10:8,9-diseco-steroid with a 14-membered macrocyclic diketone framework to have been isolated from a natural source. Herein we report a biomimetic synthesis of sarocladione in only two or seven steps from inexpensive, commercially available ergosterol. The key feature of this synthesis was a novel ruthenium-catalyzed endoperoxide fragmentation, which transformed various saturated endoperoxides into olefinic diketones by cleavage of two C?C bonds. This synthesis allowed us to unambiguously determine the structure of sarocladione and provided experimental support for its revised biosynthetic origin. This work also vividly demonstrates that consideration of the biogenesis is a powerful tool for elucidating the structures of natural products.

Novel steroidal 5α,8α-endoperoxide derivatives with semicarbazone/thiosemicarbazone side-chain as apoptotic inducers through an intrinsic apoptosis pathway: Design, synthesis and biological studies

A series of novel steroidal 5α,8α-endoperoxide derivatives bearing semicarbazone (7a-g) or thiosemicarbazone (7h-k) side chain were designed, synthesized and evaluated for their cytotoxicities in four human cancer cell lines (HepG2, HCT-116, MCF-7, and A549) using the MTT assay in vitro. The results showed that compound 7j exhibited significant cytotoxic activity against HepG2 cells (IC50 = 3.52 μM), being more potent than ergosterol peroxide. Further cellular mechanism studies in HepG2 cells indicated that compound 7j triggered the mitochondrial-mediated apoptosis by decreasing mitochondrial membrane potential (MMP), which was associated with up-regulation of Bax, down-regulation of Bcl-2, activation levels of the caspase cascade, and formation of reactive oxygen species (ROS). The above findings indicated that compound 7j may be used as a promising skeleton for antitumor agents with improved efficacy.

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).