50673-97-7

Usage

Uses

1. Hypolipidemic Applications:
17-(1,5-DIMETHYLHEXYL)-3-HYDROXY-10,13-DIMETHYL-2,3,4,5,6,7,9,10,11,12,13,15,16,17-TETRADECAHYDRO-1H-CYCLOPENTA[A]PHENANTHREN-15-ONE is used as a hypolipidemic agent for managing and reducing high levels of lipids in the blood. Its chemical structure allows it to interact with lipid metabolism pathways, potentially leading to improved cardiovascular health.
2. Pharmacological Studies:
In the field of pharmacology, 15-Ketocholestene, or 15-Ketosterol, a derivative of the compound, is used to analyze its therapeutic potential as a liver X receptor ligand. This application aims to suppress the sterol-responsive element binding protein-2 activity, which may have implications for treating various metabolic disorders.
Different Applications in Different Industries:
Used in Pharmaceutical Industry:
17-(1,5-DIMETHYLHEXYL)-3-HYDROXY-10,13-DIMETHYL-2,3,4,5,6,7,9,10,11,12,13,15,16,17-TETRADECAHYDRO-1H-CYCLOPENTA[A]PHENANTHREN-15-ONE is used as a key compound in the development of new drugs targeting lipid metabolism and related health conditions. Its unique structure and properties make it a promising candidate for creating innovative therapeutic agents.
Used in Chemical Research:
17-(1,5-DIMETHYLHEXYL)-3-HYDROXY-10,13-DIMETHYL-2,3,4,5,6,7,9,10,11,12,13,15,16,17-TETRADECAHYDRO-1H-CYCLOPENTA[A]PHENANTHREN-15-ONE is also utilized in chemical research for understanding the structure-activity relationships of various organic molecules. Its complex structure provides a basis for exploring new synthetic pathways and developing novel chemical entities with potential applications in different fields, such as materials science, agrochemistry, and environmental science.

InChI:InChI=1/C27H44O2/c1-17(2)7-6-8-18(3)23-16-24(29)25-21-10-9-19-15-20(28)11-13-26(19,4)22(21)12-14-27(23,25)5/h17-20,22-23,28H,6-16H2,1-5H3/t18-,19+,20+,22+,23-,26+,27-/m1/s1

Upstream product

• 6562-21-6 3β-(Acetyloxy)-5α-cholest-8(14)-ene 
• 86179-43-3 3β-acetoxy-8α,14α-epoxy-5α-cholestan-7β-ol 
• 7654-37-7 (3β,5α)-3-(benzoyloxy)cholest-8(14)-en-15-one 
• 5226-33-5 (3β,5α,17β)-cholesta-8,14-dien-3-ol acetate 
• 34495-42-6 3β-acetoxy-5α-cholest-8(14)-en-15-one 
• 125140-81-0 (3β,5α,7α,15α)-7-methoxy-cholest-8(14)ene-3,15-diol 3-benzoate 
• 62324-19-0 3β-benzoyloxy-14α,15α-epoxy-5α-cholest-7-ene 
• 16826-37-2 5α-cholest-7-ene-3β-ol acetate 
• 74029-63-3 3β-acetoxy-8α,14α-epoxy-5α-cholestan-7α-ol 

Downstream Products

• 55823-04-6 15-Ketocholestane 
• 444183-95-3 3β-triphenylmethoxy-5α-cholest-8(14)-en-15-one 
• 714961-59-8 3β-triphenylmethoxy-15β-hexadecanoyloxy-5α-cholest-8(14)-ene 
• 444183-96-4 3β-triphenylmethoxy-5α-cholest-8(14)-en-15-β-ol 
• 444183-97-5 Acetic acid (3S,5S,9R,10S,13R,15R,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-3-trityloxy-2,3,4,5,6,7,9,10,11,12,13,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-15-yl ester 

Relevant academic research and scientific papers

Oxygenated sterol derivatives. Their identification from the fungus-infected silkworm carcass, Bombyx cum Botryte, and their effects on growth and sterol metabolism of the silkworm, Bombyx mori

Several oxygenated sterols, e.g. ergosterol peroxide, 7-oxocholesterol and 7 β-hydroxycholesterol, were identified from the fungus-infected carcass of silkworm, Bombyx cum Botryte. However, they were nontoxic to the silkworm Bombyx mori reared on a diet containing these oxygenated sterols (0.01%) together with sitosterol or cholesterol (0.1%).

Structure-chiroptical properties relationship of cisoid enones with an α-methylenecyclopentanone unit

In the present work, the validity of sector and helicity rules correlating the stereostructure of cis-enones containing the 2-methylenecyclopentanone unit with the sign of the nπ Cotton effect (CE) observed in their electronic circular dichroism (ECD) spectra is assessed. To this end, a series of model steroid cis-enones with five-membered ketone rings was synthesized. To investigate the scope and limitations of existing rules a combination of ECD spectroscopy, X-ray analysis, and time-dependent density functional theory (TD-DFT) calculations were utilized. A comparison of the experimental ECD spectra with spectra simulated by the TD-DFT calculations gave a reasonable interpretation of the nπ CE's observed in the 360-335 nm spectral range. The results suggest that the previously articulated rules are not applicable to the investigated compounds. On the basis of comprehensive analysis of collected data, a new rule correlating perfectly the structure of studied enones with the signs of their nπ CE was proposed. This rule correlates directly the sign of the torsion angle "b" of the cyclopentanone ring of cis-enone with the sign of the nπ CE. T

Inhibitors of sterol synthesis: Synthesis and spectral properties of derivatives of 3β-hydroxy-25,26,26,26,27,27,27-heptafluoro-5α-cholest-8(14)-en-15- one fluorinated at carbon 7 or carbon 9 and their effects on 3-hydroxy-3-methylglutaryl coenzyme a reductase activity in cultured mammalian cells

As part of a program to prepare Δ8(14)-15-ketosterols that cannot readily be metabolized to cholesterol or side-chain oxygenated species, we have prepared 3β-hydroxy-7α-fluoro-5α-cholest-8(14)-en-15-one (VII) and the 9α-hydroxy (IV), 9α-fluoro (VI) and 7α-fluoro (VIII) derivatives of 3β-hydroxy-25,26,26,26,27,27,27-heptafluoro-5α-cholest-8(14)-en-15- one (II). Sterol IV was prepared by oxidation of the Δ8,14 dienol ethyl ether of the 3β-acetate of II with m-chloroperbenzoic acid, followed by mild alkaline hydrolysis of the 3β-acetate derivative of IV. Treatment of IV with hydrogen fluoride-pyridine gave VI. The 7α-fluoro-15-ketosterols VII and VIII were synthesized by treating the 3β,15-bis-trimethylsilyl Δ7,14-dienol ether derivative of the appropriate Δ8(14)-15-ketosterol with N-fluoropyridinium triflate, followed by hydrolysis of residual trimethylsilyl ethers and purification by high-performance liquid chromatography. The combined results of 1H and 13C nuclear magnetic resonance (NMR) chemical shifts, 1H-1H coupling constants, 1H-19F long-range coupling constants and molecular modeling indicated that a 7α-fluoro, 9α-fluoro or 9α-hydroxy substituent has negligible effect on the conformation of the 15-ketosterols. 1H and 13C-NMR data are also given for Δ6,8(14)- and δ8(14),9(11)-15-ketosterols, synthetic byproducts that could not be detected readily in samples of the fluoro-15-ketosterols by chromatographic methods. Mass spectra of VI and of previously reported 9α-fluoro and 9α-hydroxy-Δ8(14)-15-ketosterols showed abundant M-62 or M-60 ions that appear to correspond to loss of ketene and HF or H2O. The 9α-hydroxy-F7-15-ketosterol IV, the 7α-fluoro-15-ketosterol VII and the 7α-fluoro-F7-15-ketosterol VIII were of equivalent potency to the parent 3β-hydroxy-5α-cholest-8(14)-en-15-one (I) in lowering the levels of 3- hydrox-3-methylglutaryl coenzyme A reductase activity in CHO-K1 cells. The 9α-fluoro-F7-15-ketosterol VI showed high potency but appeared to be slightly less active than I.

Process for synthesis of 5α-cholest-8(14)-en-3β-ol-15-one and other 15-oxygenated sterols

A process for preparing 15-oxygenated sterols, such as 3β-hydroxy-5α-cholest-8(14)-ene-15 one, comprising converting 7-dehydrocholesterol to 3β-benzoyloxycholesta-5,7-diene, converting the 3β-benzoyloxycholesta-5,7-diene to a 3β-benzoyloxy-5-cholesta-7,14-diene, converting the 3β-benzoyloxy-5-cholesta-7,14-diene to a 3β-benzoyloxy-14α, 15α-epoxy-5-cholest-7-ene and converting the 3β-benzoyloxy-14α, 15α-epoxy-5-cholest-7-ene to a 15-oxygenated sterol. Preferably, the 3β-benzoyloxy-cholesta-5,7-diene is converted to a 3β-benzoyloxy-5-cholesta-7,14-diene by (i) contacting 3β-benzoyloxy-cholesta-5,7-diene, in a solvent at a temperature of at most about -55° C., with HCl at a concentration of at least about 2.0 M for a time sufficient to convert the 3β-benzoyloxycholesta-5,7-diene to a 3β-benzoyloxy-5-cholesta-7,14-diene; (ii) neutralizing the resultant reaction mixture with a base to prevent formation of a significant amount of 3β-benzoyloxy-5-cholesta-8,14-diene; and (iii) recovering the 3β-benzoyloxy-5-cholesta-7,14-diene.

Novel intermediates and an improved process for producing the compound (3β,5α)-3-hydroxycholest-8(14)-en-15-one

An improved process for the large scale production of the compound (3β,5α)-3-hydroxycholest-8(14)-en-15-one is described and two new compounds which have utility as intermediates in synthetic routes to the subject compound are disclosed.

A New Route to Steroid Ring-c Aromatization from 7-Oxygenated Steroids

3β-Acetoxy-5α-cholesta-8,14-dien-7β-ol (3), 3β-acetoxy-8α,9α-epoxy-5α-cholestan-7β-ol (6a), and 3β-acetoxy-8α,14α-epoxy-5α-cholestan-7β-ol (8a) have been aromatized with hydrochloric acid in ethanol to afford a 9:1 mixture of 12-methyl-18-nor-5α,17β(H)-cholesta-8,11,13-trien-3β-ol (4) and 12-methyl-18-nor-5α-cholesta-8,11,13-trien-3β-ol (5).By the same acidic treatment 3β-acetoxy-8α,9α-epoxy-5α-cholestan-7α-ol (6c) generates 3β-hydroxy-5α-cholest-8-en-7-one (7a), and 3β-acetoxy-8α,14α-epoxy-5α-cholestan-7α-ol (8c) affords 3β-hydroxy-5α-cholest-8(14)-en-7-one (9a) accompanied by the previously unobserved 3β-hydroxy-5α-cholest-8(14)-en-15-one (10a).