16826-35-0

Basic information

• Product Name: cholesta-4,7-dien-3-one
• Synonyms: cholesta-4,7-dien-3-one
• CAS NO: 16826-35-0
• Molecular Formula: C₂₇H₄₂O
• Molecular Weight: 382.62
• Mol File: 16826-35-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 496°Cat760mmHg
• Flash Point: 251.5°C
• Appearance: /
• Density: 0.99g/cm³
• Vapor Pressure: 5.6E-10mmHg at 25°C
• Refractive Index: 1.529
• CAS DataBase Reference: cholesta-4,7-dien-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: cholesta-4,7-dien-3-one(16826-35-0)
• EPA Substance Registry System: cholesta-4,7-dien-3-one(16826-35-0)

Safety Data

• Hazardous Substances Data: 16826-35-0(Hazardous Substances Data)

Usage

Description

Cholesta-4,7-dien-3-one is an organic compound that serves as an intermediate in the synthesis of various pharmaceutical compounds. It is characterized by its unique chemical structure, featuring a steroidal framework with double bonds at the 4 and 7 positions.

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 
• 556-91-2 aluminum tri-tert-butoxide 
• 67-64-1 acetone 
• 71-43-2 benzene 
• 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 
• 137204-84-3 2β-bromo-5β-cholest-7-en-3-one 
• 64110-20-9 cholesta-1,4,7-trien-3-one 
• 15459-85-5 5α-cholest-7-en-3-one 
• 80-99-9 lathosterol 
• 911689-01-5 3-trifluoroacetoxycholesta-3,5,7-triene 

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) 
• 16826-31-6 3.5-dinitro-benzoic acid-(cholestadien-(4.7)-yl-(3β)-ester) 
• 16826-34-9 3.5-dinitro-benzoic acid-(cholestadien-(4.7)-yl-(3α)-ester) 
• 2550-89-2 5α-cholest-7-ene-3,6-dione 
• 309958-33-6 15α-fluoro-8-lanost-8-en-3β-yl benzoate 
• 309958-29-0 Benzoic acid (3S,5R,10S,13R,14S,15S,17R)-17-((R)-1,5-dimethyl-hexyl)-15-hydroxy-4,4,10,13-tetramethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 103399-80-0 Benzoic acid (3S,5R,9R,10R,13R,17R)-17-((R)-1,5-dimethyl-hexyl)-4,4,10,13-tetramethyl-15-oxo-2,3,4,5,6,7,9,10,11,12,13,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 119288-11-8 3β-benzoyloxy-4,4-dimethyl-5α,14β-cholest-8-en-15-one 
• 119295-86-2 15α-fluorolanost-7-en-3β-yl benzoate 
• 119288-15-2 3β-benzoyloxylanost-7-en-15α-ol 
• 309958-30-3 Benzoic acid (3S,5R,9R,10R,13R,14R,15S,17R)-17-((R)-1,5-dimethyl-hexyl)-15-hydroxy-4,4,10,13-tetramethyl-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 

Relevant articles and documents

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).

Meiosis regulating compounds

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

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