747-90-0

Basic information

• Product Name: CHOLESTA-3,5-DIENE
• Synonyms: Cholestadiene;delta-(sup3,5)-cholestadien;delta(Sup3,5)-Cholestadiene;delta-3,5-Cholestadien;delta-3,5-Cholestadiene;CHOLESTERILENE;CHOLESTA-3,5-DIENE;CHOLEST-3,5-DIENE
• CAS NO: 747-90-0
• Molecular Formula: C₂₇H₄₄
• Molecular Weight: 368.64
• EINECS: 212-021-4
• Product Categories: Cholesterol and Derivatives;Lipids;Sterols
• Mol File: 747-90-0.mol
• Article Data: 57

Chemical Properties

• Melting Point: 78-80 °C(lit.)
• Boiling Point: 433.93°C (rough estimate)
• Flash Point: 225.2°C
• Appearance: /
• Density: 0.9250
• Vapor Pressure: 3.86E-08mmHg at 25°C
• Refractive Index: 1.4922 (estimate)
• Storage Temp.: −20°C
• CAS DataBase Reference: CHOLESTA-3,5-DIENE(CAS DataBase Reference)
• NIST Chemistry Reference: CHOLESTA-3,5-DIENE(747-90-0)
• EPA Substance Registry System: CHOLESTA-3,5-DIENE(747-90-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36
• WGK Germany: 3
• RTECS: FZ5600000
• Hazardous Substances Data: 747-90-0(Hazardous Substances Data)

Usage

Uses

Cholesta-3,5-diene was used as standard in HPLC in quality analysis of different types of olive oils and edible fats.

Biochem/physiol Actions

Cholesta-3,5-diene is an oxysterol, a cholesterol derivative by auto-oxidation. Oxysterols are non-genomic regulators of cholesterol homeostasis. The biological effects include protein prenylation, apoptosis, modulation of sphingolipid metabolism and platelet aggregation. Oxysterols bind to liver X receptors, modulate cholesterol efflux and decrease the uptake of cholesterol by the cells.

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/h6,11-12,19-20,22-25H,7-10,13-18H2,1-5H3/t20-,22+,23-,24+,25+,26+,27-/m1/s1

Upstream product

• 110-86-1 pyridine 
• 516-91-6 (3S,8S,9S,10R,13R,14S,17R)-3-Bromo-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene 
• 60672-57-3 3β.5-dibromo-5α-cholestane 
• 91-22-5 quinoline 
• 910-31-6 3-chloro-cholest-5-ene 
• 1182-65-6 Cholesteryltosylat 
• 910-31-6 cholesteryl chloride 
• 115792-58-0 4ξ.5-dibromo-5ξ-cholestane 
• 119-65-3 isoquinoline 
• 2930-80-5 cholesteryl iodide 
• 56-23-5 tetrachloromethane 
• 1182-65-6 cholesteryl p-toluenesulfonate 
• 151-50-8 potassium cyanide 
• 64-17-5 ethanol 

Downstream Products

• 16732-86-8 cholest-4-ene 
• 80382-29-2 (S)-17-((R)-1,5-Dimethyl-hexyl)-17-methyl-16,17-dihydro-15H-cyclopenta[a]phenanthrene 
• 481-21-0 cholestane 
• 481-20-9 5β-cholestane 
• 4117-50-4 cholesta-2,4-diene 

Relevant articles and documents

A new color reaction of steroid with anhydrous aluminum chloride and anisaldehyde. IV. Studies on the reaction mechanism.

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Novel Regio- and Stereoselective Olefin Syntheses: Hydride Abstraction from Organoiron Compounds

Treatment of the compounds η5-C5H5Fe(CO)2CHR1CH2R2 (R=H, alkyl, aryl) with Ph3C+BF4- results in abstraction of a β-hydrogen atom to give triphenylmethane and the cationic olefin complexes, 5-C5H5Fe(CO)2(CHR1CHR2)>+BF4-; liberation of the olefins can be effected by treatment with sodium iodide in acetone.The reactions have synthetic utility because (a) 1- and 2- alkyliron compounds generally give only the terminal olefin and (b) 3-alkyliron compounds give only (Z)-2-olefins.The thermodynamically more stable E internal olefins are not formed.Optimum reaction conditions and compatibility of various functional groups with the reaction conditions are also discussed.

Iridium-catalysed highly selective reduction-elimination of steroidal 4-en-3-ones to 3,5-dienes in water

Steroidal 3,5-diene is an important structural motif in steroid drugs. In this report, an iridium-catalyzed reduction-elimination of readily available steroidal 4-en-3-ones is realized to prepare steroidal 3,5-dienes. At a low catalyst loading (S/C = 200), heating 4-en-3-ones in a water-mixed organic solvent with formic acid without inert atmosphere protection afforded the desired 3,5-dienes in moderate to excellent yields. In a gram-scale preparation, recrystallization is used instead of column chromatography to purify products. Excellent functionality tolerance and regioselectivity are featured. Structural moieties such as alkanols (primary, secondary and tertiary), esters (except for formate), tolylates, and ketones (endocyclic or exocyclic) are not affected. Surprisingly, the reduction-elimination only takes place at A-ring 4-en-3-ones. In addition, bicyclic 4-en-3-ones are also viable substrates. Synthetic applications of steroidal 3,5-dienes are demonstrated. Our method can also lead to steroidal 3,5-dienes-3-d (>99% d-incorporation) when DCO2D and D2O are used together.

Electrochemical synthesis of glycoconjugates of 3β-hydroxy- Δ5-steroids by using non-activated sugars and steroidal thioethers

A new protocol for the electrochemical synthesis of glycoconjugates is presented. Thioether derivatives of cholesterol and other sterols were subjected to anodic oxidation in the presence of a sugar alcohol affording glycoconjugates with the sugar linked to a steroid moiety by an ether bond. The isomeric 6β-3α,5α-cyclo-steroidal thioethers proved to be better sterol donors than the normal 3β-Δ5-steroidal thioethers.