809-51-8

Usage

Uses

Used in Pharmaceutical Industry:
7-oxocholest-5-en-3-beta-yl acetate is used as an intermediate for the synthesis of cholesterol derivatives and metabolites, which are essential in the development of drugs targeting various health conditions.
Used in Chemical Research:
7-oxocholest-5-en-3-beta-yl acetate is utilized as a research compound in the study of cholesterol metabolism and the development of novel therapeutic agents.
Used in Cosmetic Industry:
7-oxocholest-5-en-3-beta-yl acetate is employed as a key ingredient in the formulation of cosmetic products, particularly those targeting skin health and anti-aging benefits.
Used in Analytical Chemistry:
7-oxocholest-5-en-3-beta-yl acetate is used as a reference standard in analytical methods for the detection and quantification of cholesterol and its derivatives in various samples.

Upstream product

• 604-35-3 cholesteryl acetate 
• 604-35-3 3-β-acetoxycholest-5-one 
• 31220-43-6 3β-Acetoxycholest-5-en-7-one oxime 
• 110-86-1 pyridine 
• 70865-00-8 3β-acetoxy-6β-bromo-5α-cholestan-7-one 
• 70864-92-5 3β-acetoxy-6α-bromo-5α-cholestan-7-one 
• 19317-89-6 3β-acetoxycholest-6-en-5α-ol 
• 2867-93-8 i-cholesteryl methyl ether 
• 987-53-1 3β-acetoxy-5α-cholest-6-ene 
• 17974-77-5 3β-acetoxy-7β-hydroxycholest-5-ene 
• 75-91-2 tert.-butylhydroperoxide 
• 604-35-3 Cholesteryl acetate 
• 112-79-8 Elaidic acid 
• 60-33-3 (9E,12E)-Octadeca-9,12-dienoic acid 

Downstream Products

• 567-72-6 cholest-3,5-dien-7-one 
• 3839-09-6 3α-5-cyclo-5α-cholestan-6-one 
• 135705-63-4 7-oxo-3-(1'-carbethoxypropan-2'-one)-cholest-5-ene 
• 149280-65-9 7ξ-phenyl-cholestene-(5)-diol-(3β.7ξ) 
• 566-26-7 (3S,7S,8S,9S,10R,13R,14S,17R)-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-3,7-diol 
• 566-27-8 cholest-5-en-3β,7β-diol 
• 40823-16-3 acetic acid-(7β-hydroxy-5α-cholestanyl-(3β)-ester) 
• 79732-44-8 cholest-5-en-7-one 
• 105220-77-7 3ξ,4ξ-Cyclopropanocholest-5-en-7-one 
• 19317-90-9 7α-hydroxycholest-5-en-3β-yl 3-acetate 
• 17974-77-5 3β-acetoxy-7β-hydroxycholest-5-ene 
• 17974-77-5 cholest-5-ene-3β,7-diol 3-monoacetate 
• 95732-63-1 4β-hydroxy-7-oxocholest-5-en-3β-yl acetic acid γ-lactone 
• 130251-44-4 7-oxocholest-5-en-3β,4α-yl diacetate 

Relevant academic research and scientific papers

Catalytic cyclometallation in steroid chemistry V: Synthesis of hybrid molecules based on steroid oximes and (5Z,9Z)-tetradeca-5,9-dienedioic acid as potential anticancer agents

Synthetic analogues of natural 5Z,9Z-dienoic acids - hybrid molecules based on the oximes of cholesterol, pregnenolone, and androsterone with 1,14-tetradeca-5Z,9Z-dienedicarboxylic acid - were synthesized for the first time and studied for antitumor activity in vitro. The acid was prepared using catalytic cyclomagnesiation of O-containing 1,2-dienes with Grignard reagent in the presence of Cp2TiCl2 as the key step. Using flow cytometry, it was shown for the first time that the new molecules are efficient apoptosis inducers in the HeLa, Hek293, U937, Jurkat, and K562.

Synthesis of new 7-aminosterol squalamine analogues with high antimicrobial activities through a stereoselective titanium reductive amination reaction

A series of 7-amino- and polyaminosterol analogues of squalamine and trodusquemine were synthesized involving a new stereoselective titanium reductive amination reaction in high chemical yields of up to 95% in numerous cases. These derivatives were evaluated for their in vitro antimicrobial properties against human pathogens. All the compounds present excellent activities against Gram-positive bacteria exhibiting similar results against Staphylococcus aureus and Streptococcus faecalis with minimum inhibitory concentrations (MICs) varying from 2.5 to 10 μg/mL. Numerous derivatives possess also MICs against Gram-negative Escherichia coli bacteria (MICs varying from 2.5 to 10 μg/mL) suggesting that nature of the amino group attached to the sterol moiety plays an important role on the activities of such products.

Partial separation of enantiomeric 1,2-diols via ketal formation with a polymer-supported chiral ketone

Partial separations of the (R,R)- and (S,S)-enantiomers of butane-2,3-diol, trans-cyclohexane-1,2-diol and dimethyl tartrate were achieved via ketal formation with a polymer-supported 7-keto steroid; in each case one enantiomer reacted in higher yield than the other and release of the diols from the support gave diol fractions significantly enriched in one enantiomer.

Synthesis of 7α- and 7β-spermidinylcholesterol, squalamine analogues

Stereoselective synthesis of squalamine dessulfates analogues, 7α and 7β-N-[3N-(4-aminobutyl) aminopropyl]aminocholesterol are reported, using 7α and 7β-aminocholesterol as a key intermediate. It's the first example in which the position of spermidine is modified at the steroid ring. These molecules showed a comparable antibacteria and fungi activities to squalamine. Then, they have a cytotoxic activity on a human non-small cell bronchopulmonary carcinoma line (NSCLC-N6).

Preparation method of 7-keto-cholesterol acetate

The invention relates to a preparation method of 7-keto-cholesteryl acetate. Specifically, according to the method provided by the invention, cholesteryl acetate is taken as a raw material, Salen Cu (II) is taken as a catalyst, air or pure oxygen is taken as an oxidant, and the 7-keto-cholesteryl acetate is prepared with high yield, high purity, simple process and low cost.

Novel industrial method for preparing vitamin D3 by taking stigmasterol as raw material

The invention provides a novel industrial method for preparing vitamin D3 by taking stigmasterol as a raw material. The method comprises the following steps: sequentially carrying out hydroxyl acetylation, side chain oxidation, side chain isopentane reduction and hydrogenation on stigmasterol to obtain cholesterol acetate, and then sequentially carrying out oxidation, hydrazone formation, hydrazone removal, hydrolysis, illumination and the like to obtain the vitamin D3. The invention provides a novel method for preparing vitamin D3 from stigmasterol, and the method has the advantages of mild reaction conditions and high yield, and is suitable for industrial production.

Cooperative Noncovalent Interactions Lead to a Highly Diastereoselective Sulfonyl-Directed Fluorination of Steroidal α,β-Unsaturated Hydrazones

A series of steroidal α,β-unsaturated hydrazones is presented whose behavior and reactivity are governed by various types of weak C-H hydrogen bonds. Several interesting features in a representative X-ray crystal structure and 1H NMR spectrum are examined that provide evidence for a unique bifurcated intramolecular C-H interaction. Moreover, these steroid derivatives undergo functionalization in the form of a highly regio- and stereoselective fluorination; the sulfonyl oxygen atoms are proposed to direct the fluorinating reagent through C-H hydrogen bonds.

Preparation method and application of 7-ketocholesterol acetate

The invention relates to a preparation method of 7-ketocholesterol acetate. The preparation method comprises the following steps: (1) dissolving cholesterol acetate, a catalyst, an initiator and an antioxidant in a mixed solvent to obtain a first mixed solution, and introducing oxygen into the first mixed solution to perform oxidation reaction on cholesterol acetate and oxygen to obtain a second mixed solution; and (2) treating the second mixed solution to obtain the 7-ketocholesterol acetate. The invention also relates to an application of the 7-ketocholesterol acetate obtained by the preparation method in preparation of 7-dehydrocholesterol. According to the preparation method, the antioxidant is added so that free radicals of reactants in a reaction system can be effectively prevented from being subjected to polymerization reaction, the reaction selectivity can be improved, and the yield and the purity of the target product 7-ketocholesterol acetate can be improved.

7-keto-cholesterol acetate preparation method

The invention discloses a 7-keto-cholesterol acetate preparation method, wherein the preparation method comprises the following steps: (1) carrying out an oxidation reaction on cholesterol acetate andair in a reaction solvent under the catalysis of an N-hydroxyl derivative and a transition metal salt, and controlling the conversion rate of the oxidation reaction to be 60-80% to obtain an oxidation reaction liquid; and (2) concentrating the oxidation reaction solution to remove the reaction solvent, then adding an extraction solvent, separating out the N-hydroxyl derivative, then adding aceticanhydride and an organic alkali to carry out a dehydration reaction, and after the reaction is completed, carrying out post-treatment to obtain the 7-keto-cholesterol acetate product and a cholesterol acetate raw material. By adopting the preparation method disclosed by the invention, byproducts of the oxidation reaction can be reduced, and the total yield of the reaction and the purity of the 7-keto-cholesterol acetate product are improved.

Preparation method for intermediate, namely 7-ketocholesterol acetate of vitamin D3

The invention discloses a preparation method for an intermediate, namely 7-ketocholesterol acetate of vitamin D3. The preparation method comprises the following steps: under the actions of a main catalyst, a cocatalyst and an initiator, carrying out an oxidation reaction on cholesterol acetate by using oxygen as an oxidant, and carrying out after-treatment after the reaction is finished so as to obtain the 7-ketocholesterol acetate, wherein the main catalyst is N-hydroxyphthalimide; the cocatalyst is water-absorbent resin; and the initiator is at least one selected from the group consisting ofmanganese acetate and cobalt acetate. According to the invention, by adoption of the water-absorbent resin (SAP) as the cocatalyst, generation of the oxidation reaction can be effectively promoted, so the yield of a product is improved, and the mode of after-treatment is simplified; meanwhile, the main catalyst and the cocatalyst are cheap and easily available, and can be recycled for six times or more; high reaction selectivity and high conversion rate are achieved; and the preparation method is highly-efficient and has low cost.