16826-35-0

Usage

Uses

Used in Pharmaceutical Industry:
Cholesta-4,7-dien-3-one is used as an intermediate in the synthesis of Methost-7-enol (M260640) for its potent inhibitory activity against human cancer cell lines. This includes liver cancer, nasopharyngeal, and colon cancer cells, making it a valuable compound in the development of anticancer drugs.
In the synthesis process, Cholesta-4,7-dien-3-one plays a crucial role in creating Methost-7-enol, which has demonstrated significant potential in combating various types of cancer. Its application in the pharmaceutical industry is primarily due to its ability to contribute to the development of effective cancer treatments.

InChI:InChI=1/C27H42O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h10,17-19,23-25H,6-9,11-16H2,1-5H3/t19-,23-,24+,25+,26+,27-/m1/s1

Upstream product

• 434-16-2 7-dehydrocholesterol 
• 103326-74-5 3,3-ethanediyldioxy-cholesta-5,7-diene 
• 556-91-2 aluminum tri-tert-butoxide 
• 67-64-1 acetone 
• 71-43-2 benzene 
• 64110-20-9 cholesta-1,4,7-trien-3-one 
• 137204-84-3 2β-bromo-5β-cholest-7-en-3-one 
• 177962-82-2 cholesta-5,8(14)-dien-3β-ol 
• 3496-88-6 3,3-ethane-1,2-diyldioxy-cholest-5-ene 
• 601-57-0 Cholest-4-en-3-one 
• 29374-80-9 5β-cholest-7-en-3-one 
• 137329-00-1 2α,4α-dibromo-5α-cholest-7-en-3-one 
• 15459-85-5 5α-cholest-7-en-3-one 
• 80-99-9 lathosterol 

Downstream Products

• 434-16-2 7-dehydrocholesterol 
• 57651-84-0 cholesta-5,7-dien-3α-ol 
• 16826-32-7 3α-hydroxy-10.13-dimethyl-17β-((R)-1.5-dimethyl-hexyl)-gonadiene-(4.7) 
• 16826-29-2 3β-hydroxy-10.13-dimethyl-17β-((R)-1.5-dimethyl-hexyl)-gonadiene-(4.7) 
• 15459-85-5 5α-cholest-7-en-3-one 
• 29374-80-9 5β-cholest-7-en-3-one 
• 53296-71-2 (3β,20R)-4,4-dimethylcholesta-5,7-dien-3-ol 
• 108348-03-4 15-oxolanost-7-en-3β-yl benzoate 
• 116928-45-1 3β-benzoyloxy-32-nor-lanost-8(14)-ene 
• 103399-79-7 (3β,5α,20R)-4,4-dimethylcholesta-8,14-dien-3-ol benzoate 
• 309958-27-8 Benzoic acid (3S,5R,8R,9S,10R,13R,17R)-17-((R)-1,5-dimethyl-hexyl)-4,4,10,13-tetramethyl-2,3,4,5,6,7,8,9,10,11,12,13,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 309958-28-9 Benzoic acid (3S,5R,8R,9S,10R,13R,14R,15S,17R)-17-((R)-1,5-dimethyl-hexyl)-4,4,10,13-tetramethyl-hexadecahydro-20-oxa-cyclopropa[14,15]cyclopenta[a]phenanthren-3-yl ester 
• 309958-25-6 Benzoic acid (3S,5R,8R,9S,10R,13R,14S,17S)-14-chloro-17-((R)-1,5-dimethyl-hexyl)-4,4,10,13-tetramethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 
• 119288-17-4 3β-benzoyloxy-4,4-dimethyl-5α-cholest-7-en-15-one 

Relevant academic research and scientific papers

Synthesis of fluorescent 4,6,8(14)-trien-3-one steroids via 3,5,7-trien- 3-ol ethers. Important probes for steroid-protein interactions

A general synthesis of fluorescent 4,6,8(14)-trien-3-one steroids with and without an aliphatic side chain is described via 3-alkoxy-3,5,7-trienes as intermediates. The advantages of this method are general applicability, good yields, limited number of reaction steps (up to four), and ready availability of starting materials (at low cost). a) Starting from ergosterol (1) or cholesta-5,7-dien-3-ol (2) and oxidizing them to ergosta-4,7,22-trien-3-one (3) or cholesta-4,7-dien-3-one (4) we synthesized the enol ethers (5) and (6). Subsequent treatment with DDQ gave the 4,6,8(14),22-tetraen-3-one (7) and the 4,6,8(14)-trien-3-one (8). b) Similarly 17β-(I-oxopropoxy)-androsta- 4,6,8(14)-trien-3-one (13) was obtained, but the required enol ether was synthesized via the 4,6-dien-3-one (11).

A new route to precursors of ecdysteroids using a regio- and stereoselective hydroboration

We have developed a new route to precursors of ecdysteroids, using a regio- and stereoselective hydroboration. Hydroboration of 3,3-(ethylenedioxy)-cholesta-5,7-diene (from 7-dehydrocholesterol in two steps), followed by oxidation with alkaline hydrogen peroxide, produces 3,3-(ethylenedioxy)-5β-cholest-7-en-6β-ol (the same reaction with 7-dehydrocholesterol leads only to the 5α-alcohol (OH-6α), prohibiting the synthesis of 5β-steroids).

A convenient method for the preparation of Δ4,7-steroidal 3-ketones and Δ5,7 sterols

A method is described for the preparation of Δ4,7-steroidal ketones or Δ5,7-sterols from Δ5-sterols via the sequence Wettstein-Oppenauer oxidation, trifluoroacetylation to give the Δ2,4,6-enol ester, and acid catalyzed isomerization to the Δ3,5,7-enol ester, followed by acid hydrolysis, or sodium borohydride reduction, respectively.

Meiosis regulating compounds

Certain novel sterol derivatives can be used for regulating the meiosis in oocytes and in male germ cells.

Synthesis of 15alpha-fluoro-24,25-dihydrolanosterol as a potential inhibitor and/or mechanistic probe for lanosterol 14alpha-demethylase.

As a potential inhibitor and/or mechanistic probe for lanosterol 14alpha-demethylase, 15alpha-fluoro-24,25-dihydrolanosterol was prepared by fluorination of 15alpha-hydroxy-24,25-dihydrolanost-7-en-3beta-yl benzoate with diethylaminosulfur trifluoride, followed by hydrogen chloride-catalyzed isomerization of the delta7 to delta8 and reductive cleavage of the benzoate.

Synthesis of potential inhibitors of the biosynthesis of ecdysone, the moulting hormone of insects

We have synthesized new potential acetylenic inhibitors of the last step in the biosynthesis of ecdysone, the moulting hormone of insects.The key step in our synthesis is the introduction of the A/B cis ring junction (5β-H configuration) by regio- and stereoselective hydroboration of the Δ5 double bond (B-ring) of 7-dehydrocholesterol. - Keywords: ecdysteroid / ecdysteroid inhibitors / hydroboration / acetylenic derivatives

Synthesis of a tritiated 3-dehydroecdysteroid putative precursor of ecdysteroid biosynthesis in Locusta migratoria

We have synthesized a tritiated form of 14α-hydroxy-5β-cholest-7-ene-3,6-dione (5β-diketol) of high specific activity (1.74 TBq/mmol) from 7-dehydrocholesterol in seven steps with stereoselective introduction of the A/B cis ring junction as the key reaction. We have examined the ability of endocrine glands (prothoracic glands) of Locusta migratoria to use this molecule as a precursor of 3-dehydroecdysone and of ecdysone biosynthesis. A very efficient conversion of 5β-diketol to ecdysone and to 3-dehydroecdysone was monitored, which opens up new possibilities for the understanding of the role of 3-dehydro-compounds in ecdysteroid biosynthesis.