747-90-0

Usage

Uses

Used in Quality Analysis of Olive Oils and Edible Fats:
Cholesta-3,5-diene is used as a standard in High-Performance Liquid Chromatography (HPLC) for the quality analysis of different types of olive oils and edible fats. It serves as a reference compound to ensure the accuracy and reliability of the analytical results, helping to determine the purity, composition, and authenticity of these oils and fats. This application is particularly important in the food industry, where maintaining product quality and safety is paramount.

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

• 51467-52-8 6β-chloro-cholest-4-ene 
• 67-64-1 acetone 
• 110-89-4 piperidine 
• 3381-56-4 3α-(toluene-4-sulfonyloxy)-cholest-5-ene 
• 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 
• 108-89-4 picoline 
• 1182-65-6 cholesteryl p-toluenesulfonate 
• 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 

Downstream Products

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

Relevant academic research and scientific papers

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.

Mild olefin formationviabio-inspired vitamin B12photocatalysis

Dehydrohalogenation, or elimination of hydrogen-halide equivalents, remains one of the simplest methods for the installation of the biologically-important olefin functionality. However, this transformation often requires harsh, strongly-basic conditions, rare noble metals, or both, limiting its applicability in the synthesis of complex molecules. Nature has pursued a complementary approach in the novel vitamin B12-dependent photoreceptor CarH, where photolysis of a cobalt-carbon bond leads to selective olefin formation under mild, physiologically-relevant conditions. Herein we report a light-driven B12-based catalytic system that leverages this reactivity to convert alkyl electrophiles to olefins under incredibly mild conditions using only earth abundant elements. Further, this process exhibits a high level of regioselectivity, producing terminal olefins in moderate to excellent yield and exceptional selectivity. Finally, we are able to access a hitherto-unknown transformation, remote elimination, using two cobalt catalysts in tandem to produce subterminal olefins with excellent regioselectivity. Together, we show vitamin B12to be a powerful platform for developing mild olefin-forming reactions.

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.

3α,5α-Cyclocholestan-6β-yl ethers as donors of the holesterol moiety for the electrochemical synthesis f cholesterol glycoconjugates

3α,5α-Cyclocholestan-6β-yl alkyl and aryl ethers were proved to be efficient cholesteryl donors in the electrochemical synthesis of glycoconjugates. 3α,5α-Cyclocholestan-6β-ol (i-cholesterol) and its tert-butyldimethylsilyl ether can also be used for this

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.

Dehydrative glycosylation with the Hendrickson reagent

The Hendrickson reagent is able to perform efficiently dehydrative glycosylation of 1-hydroxyglycosyl donors. The reaction occurs under mild conditions through an anomeric oxophosphonium intermediate detected by nuclear magnetic resonance. Further insight into the mechanism was gained by 18O labeling of anomeric OH.

Convenient synthesis of monomeric steroids from steroidal oxalate dimers using flash vacuum pyrolysis (FVP)

Flash vacuum pyrolysis (FVP) or thermolysis (FVT), an environmentally friendly method for studying organic reaction mechanisms as well as synthesis, was applied to a series of oxalate dimers (1, 3, 5, 7, 9, 11, 13, and 15) to synthesise monomeric enes, dienes, and a triene (2, 4, 6, 8, 10, 12, 14, and 16). All steroidal monomers were identified by spectroscopic means. TUBITAK.

Reduction of alkyl and vinyl sulfonates using the CuCl2· 2H2O-Li-DTBB(cat.) system

The reduction of a series of alkyl mesylates, dimesylates and triflates to the corresponding hydrocarbons was efficiently performed using a reducing system composed of CuCl2·2H2O, an excess of lithium sand and a catalytic amount (5 mol%) of 4,4′-di-tert-butylbiphenyl (DTBB), in tetrahydrofuran at room temperature. The process was also applied to enol and dienol triflates affording alkenes and dienes, respectively. The use of the deuterated copper salt CuCl2·2D2O allowed the simple preparation of the corresponding deuterated products.

Tetramethyldiamidophosphoric acid chloride mediated epoxide-diene conversion and steroidal aromatization

The reaction of tetramethyldiamidophosphoric acid chloride with epoxides in the presence of a trace amount of water furnished 1,3-dienes in good yield. The conversion works with open chain and cyclic epoxides. A C-C bond cleavage reaction occurs if the epoxide contains a quaternary carbon. Application of this method to epoxy sterols afforded ring A aromatic steroids in good yield. The aromatization works via dienol-benzene rearrangements and is independent of the C-3 stereochemistry.

Solvolysis of sterol tosylates in aqueous dimethylformamide

It has been established that the heating of the sterol tosylates (1a - c) in aqueous dimethylformamide in the presence of sodium acetate leads to the formation of the 3α,5-cyclo-6β-alcohols (2), the sterols (3), the 3,5-dienes (4), and the sterol formates (5).