567-72-6

Basic information

• Product Name: cholesta-3,5-dien-7-one
• Synonyms: cholesta-3,5-dien-7-one;7-Ketocholesta-3,5-diene;Cholesta-3,5-diene-7-one-d7
• CAS NO: 567-72-6
• Molecular Formula: C₂₇H₄₂O
• Molecular Weight: 382.62178
• EINECS: 209-305-5
• Mol File: 567-72-6.mol
• Article Data: 21

Chemical Properties

• Melting Point: 114 °C
• Boiling Point: 494°Cat760mmHg
• Flash Point: 250.7°C
• Appearance: /
• Density: 0.99g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.53
• CAS DataBase Reference: cholesta-3,5-dien-7-one(CAS DataBase Reference)
• NIST Chemistry Reference: cholesta-3,5-dien-7-one(567-72-6)
• EPA Substance Registry System: cholesta-3,5-dien-7-one(567-72-6)

Safety Data

• Hazardous Substances Data: 567-72-6(Hazardous Substances Data)

Usage

General Description

Cholesta-3,5-dien-7-one, also known as 7-oxocholesterol, is a steroidal compound found in the human body and in various foods. It is a type of oxysterol, which are oxidized derivatives of cholesterol. 7-oxocholesterol has been studied for its potential role in cardiovascular disease and other health conditions. It is also known to be involved in the regulation of lipid metabolism and inflammation. Additionally, 7-oxocholesterol has been linked to the progression of neurodegenerative diseases such as Alzheimer's and Parkinson's. Research on the effects and mechanisms of action of cholesta-3,5-dien-7-one is ongoing, with potential implications for human health and disease.

InChI:InChI=1/C27H42O/c1-18(2)9-8-10-19(3)21-12-13-22-25-23(14-16-27(21,22)5)26(4)15-7-6-11-20(26)17-24(25)28/h6,11,17-19,21-23,25H,7-10,12-16H2,1-5H3/t19-,21-,22+,23+,25?,26+,27-/m1/s1

Upstream product

• 809-51-8 3β-acetoxycholest-5-en-7-one 
• 57-88-5 cholesterol 
• 80108-85-6 3β-methanesulphonyloxy-5-cholesten-7-one 
• 566-28-9 3β-hydroxy-5-cholesten-7-one 
• 570-74-1 cholest-5-ene 
• 148673-94-3 (8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-7-phenylsulfanyl-1,2,8,9,10,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one 
• 148673-89-6 (8S,9S,10R,13R,14S,17R)-7-Bromo-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-1,2,8,9,10,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one 
• 67-56-1 methanol 
• 809-51-8 7-ketocholesteryl acetate 
• 64-19-7 acetic acid 
• 55105-71-0 3β-chlorocholest-5-en-7-one 
• 127-08-2 potassium acetate 
• 109-52-4 valeric acid 
• 71496-99-6 cholest-5-en-7-on-3α-ol acetate 

Downstream Products

• 19037-34-4 5α-cholestan-7β-ol 
• 567-71-5 5α-cholestan-7-one 
• 1450594-13-4 C₃₃H₄₇N₃O₂ 
• 6673-62-7 7β-(toluene-4-sulfonyloxy)-5α-cholestane 
• 481-21-0 cholestane 
• 19682-30-5 7α-aza-B-homocholesta-3,5-dien-7-one 

Relevant articles and documents

Neuroactive Type-A γ-Aminobutyric Acid Receptor Allosteric Modulator Steroids from the Hypobranchial Gland of Marine Mollusk, Conus geographus

In a program to identify pain treatments with low addiction potential, we isolated five steroids, conosteroids A-E (1-5), from the hypobranchial gland of the mollusk Conus geographus. Compounds 1-5 were active in a mouse dorsal root ganglion (DRG) assay that suggested that they might be analgesic. A synthetic analogue 6 was used for a detailed pharmacological study. Compound 6 significantly increased the pain threshold in mice in the hot-plate test at 2 and 50 mg/kg. Compound 6 at 500 nM antagonizes type-A γ-aminobutyric acid receptors (GABAARs). In a patch-clamp experiment, out of the six subunit combinations tested, 6 exhibited subtype selectivity, most strongly antagonizing α1β1γ2 and α4β3γ2 receptors (IC50 1.5 and 1.0 μM, respectively). Although the structures of 1-6 differ from those of known neuroactive steroids, they are cell-type-selective modulators of GABAARs, expanding the known chemical space of neuroactive steroids.

P -TsOH-Catalyzed one-pot transformation of di- and trihydroxy steroids towards diverse A/B-ring oxo-functionalization

A solid support-mediated p-TsOH-catalyzed milder transformative protocol was developed to furnish diverse ring-A and/or ring-B oxo-functionalized steroids. To furnish interesting isomers involving the A/B-ring of biomolecules in a one-pot approach, only solid supports (and not solution!) were found to be effective. p-TsOH/SiO2-oxidation of 4β-hydroxycholesterol, the major oxysterol in human circulation, into a mixture of cholest-4-en-3-one, cholest-4-ene-3,6-dione, and 5α-cholestane-3,6-dione was the starting point for the investigations herein. The reaction protocol was optimized in detail, and efforts were carried out toward gaining an understanding of the mechanistic aspects favoring the solid support, and a possible synergetic catalytic system involving p-TsOH and SiO2 was expected to be a key part. Application of the novel methodology to 4β,7α-dihydroxy steroids resulted in the desired diverse ketosteroids through oxidation/oxidative dehydration, which generalized the process as a facile multi-oxo-functionalization steroidal transformation.

Cholesterol transformations during heat treatment

The aim of the study was to characterise products of cholesterol standard changes during thermal processing. Cholesterol was heated at 120 °C, 150 °C, 180 °C and 220 °C from 30 to 180 min. The highest losses of cholesterol content were found during thermal processing at 220 °C, whereas the highest content of cholesterol oxidation products was observed at temperature of 150 °C. The production of volatile compounds was stimulated by the increase of temperature. Treatment of cholesterol at higher temperatures i.e. 180 °C and 220 °C led to the formation of polymers and other products e.g. cholestadienes and fragmented cholesterol molecules. Further studies are required to identify the structure of cholesterol oligomers and to establish volatile compounds, which are markers of cholesterol transformations, mainly oxidation.