4117-50-4

Usage

Uses

Used in Pharmaceutical Industry:
1,4-CHOLESTADIEN-3-ONE is used as a precursor for the synthesis of various steroid-based drugs, including hormones such as testosterone, estrogen, and cortisol. Its role in the production of these hormones makes it an essential component in the development of medications for hormonal imbalances and related conditions.
Used in Medical Research:
1,4-CHOLESTADIEN-3-ONE is used as a subject of study for its potential biological activities, such as anti-inflammatory and anti-tumor properties. Researchers are exploring its therapeutic potential in the treatment of various diseases and conditions, including inflammatory disorders and cancer.
Used in Hormone Replacement Therapy:
1,4-CHOLESTADIEN-3-ONE is used as a starting material for the synthesis of hormones used in hormone replacement therapy. It helps in the production of medications that address hormonal imbalances, such as those experienced during menopause or andropause.
Used in Steroid Compound Synthesis:
1,4-CHOLESTADIEN-3-ONE is used as an intermediate in the synthesis of various steroid compounds, which have a wide range of applications in the pharmaceutical industry. These compounds are used in the development of medications for various conditions, including allergies, asthma, and inflammatory diseases.

InChI:InChI=1/C27H44/c1-19(2)9-8-10-20(3)23-14-15-24-22-13-12-21-11-6-7-17-26(21,4)25(22)16-18-27(23,24)5/h6-7,11,17,19-25H,8-10,12-16,18H2,1-5H3/t20-,21?,22+,23-,24+,25+,26+,27-/m1/s1

Upstream product

• 57-88-5 cholesterol 
• 566-88-1 dihydrocholesterone 
• 57-88-5 cholesterol 
• 56-23-5 tetrachloromethane 
• 566-90-5 cholest-4-en-3α-ol 
• 142183-59-3 Carbonic acid (3R,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester methyl ester 
• 138814-69-4 Formic acid (3R,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 21301-41-7 cholest-4-en-3-one tosylhydrazone 
• 517-10-2 allocholesterol 
• 747-90-0 3,5-cholestadiene 

Downstream Products

• 16732-86-8 cholest-4-ene 
• 747-90-0 3,5-cholestadiene 
• 20233-47-0 4β,5-dihydroxy-5α-cholestane 

Relevant academic research and scientific papers

Diene Geometry and Allylic Axial Chirality Effect

The sense of the contribution of polarizable allylic axial bonds to the ?-?* Cotton effect of dienes is found to be determined by the chirality of the system which is defined by the direction of the transition moment and direction of the allylic bond.

A novel preparative method for homo- and heteroannular conjugated dienes in decalin derivatives by the palladium-catalyzed regioselective elimination reaction of allylic carbonates under mild conditions

Homoannular conjugated dienes in decalin systems can be prepared by the palladium-catalyzed elimination reaction of α-allylic carbonates and heteroannular dienes are obtained from β-allylic carbonates.

Stereocontrolled formation of cis and trans ring junctions in hydrindane, decalin, and steroid systems by palladium-catalyzed regioselective and stereospecific hydrogenolysis of allylic formates

Both the cis and trans ring junctions can be generated selectively in hydrindane, decalin and steroid systems by the palladium-catalyzed regioselective and stereospecific decarboxylation-hydrogenolysis of allylic formates. The trans junctions were formed from 3β allylic formates of decalin and steroid and 5β allylic formates of hydrindane. The corresponding 3α and 5α formates generate the cis ring junction.

Stereocontrolled Formation of Cis and Trans Ring Junctions in Hydrindane and Decalin Systems by Palladium-Catalyzed Regioselective and Stereospecific Hydrogenolysis of Allylic Formates

Both cis and trans ring junctions can be generated selectively in hydrindane, decalin, and steroid systems by the palladium-catalyzed regioselective and stereospecific hydrogenolysis of allylic formates.

Two Factors in Thermal Cis-Trans Rearrangement of Pentaenes: Configuration in (E,E)-Octahydro-2,2′-bi-3H-naphthylidene. Extensivity in 2,2′and 3,3′-Bicholestadienylidenes

Useful interaction between theory and practice in the syn-anti thermal rearrangement of polyenes depends on transferability of theoretically calculated enthalpies of activation, which are intrinsically gas-phase, to experiment, which are most often conducted in solution. The choice of all-trans polyenes for further experimental extension of our limited knowledge led us to worry how coupling of motions required to attain the transition state with motions and translocations in the solvent might cause the resulting activation parameters to deviate from their hypothetical gas-phase values. We have compared two isomeric pentaenes that present substantial differences in the degree of their extension into the solvent; that is, in their "extensivity". Because our pragmatically selected substrates 2,2"- and 3,3"-bicholestadienylidenes (2 and 3, respectively) did not have identical configurations, model compounds (E,Z)-5 and (E,E)-5 were compared and found to have ΔH? = 34.0 and 32.1 kcal/mol, respectively. An even greater difference between 2 and 3, 36.1 and 31.6 kcal/mol, respectively, points to an additional factor. We have apportioned the discrepancy between a configurational factor of 1.9 kcal/mol and an "extensivity" factor of 2.6 kcal/mol. This latter factor is tentatively ascribed to the operation of Kramers' dynamical concept of solvent friction.

Oxygenation of 1-t-Butylcyclohexa-1,3-diene and Cholesta-2,4-diene in the Presence of Trityl Tetrafluoroborate

Whereas the oxygenation of 1-t-butylcyclohexa-1,3-diene (4) in the presence of catalytic amounts of trityl tetrafluoroborate in dichloromethane at -78 deg C under irradiation from a tungsten lamp gives two dimeric epidioxides as major products, cholesta-2