3464-50-4

Usage

Uses

Used in Pharmaceutical and Biochemical Production:
Cholesteryl chloroacetate is utilized as a precursor in the synthesis of various cholesterol derivatives, which are essential for the development of pharmaceuticals and biochemicals. Its role in the production process is crucial for creating compounds with specific therapeutic properties.
Used in Research and Development of Lipid-based Drug Delivery Systems:
In the field of drug delivery, cholesteryl chloroacetate is employed as a component in the research and development of lipid-based systems. Its incorporation aids in enhancing the solubility, stability, and targeted delivery of drugs, thereby improving their bioavailability and therapeutic efficacy.
Used in Cardiovascular Disease Research:
Cholesteryl chloroacetate is used as a research tool in studying cardiovascular diseases due to its connection with cholesterol metabolism. Understanding its role helps in developing treatments and preventive measures for conditions such as atherosclerosis and other related disorders.
Used in Atherosclerosis and Metabolic Disorders Research:
CHOLESTERYL CHLOROACETATE is also instrumental in investigations related to atherosclerosis and metabolic disorders. Its involvement in cholesterol metabolism makes it a valuable asset in exploring the pathophysiology of these diseases and identifying potential therapeutic targets.

InChI:InChI=1/C29H47ClO2/c1-19(2)7-6-8-20(3)24-11-12-25-23-10-9-21-17-22(32-27(31)18-30)13-15-28(21,4)26(23)14-16-29(24,25)5/h9,19-20,22-26H,6-8,10-18H2,1-5H3

Upstream product

• 57-88-5 cholesterol 
• 79-11-8 chloroacetic acid 
• 79-04-9 chloroacetyl chloride 
• 57-88-5 cholesterol 
• 17608-41-2 cholestanol 
• 541-88-8 Chloroacetic anhydride 

Downstream Products

• 1234312-47-0 Br^(1-)*C₆₃H₁₀₁N₆O₈⁽¹⁺⁾ 
• 352709-90-1 1-(cholesteryloxycarbonylmethyl)-1,6-dibenzyl-1,6-diazaoctane 
• 352709-99-0 N,N'-bis-(cholesteryloxycarbonylmethyl)-N,N'-dibenzyl-1,4-diaminobutane 
• 57-88-5 cholesterol 
• 123191-82-2 cholesteryl 2-(dimethylamino)acetate 
• 747-90-0 3,5-cholestadiene 
• 73670-26-5 Gly-OCho 

Relevant academic research and scientific papers

Calix[4]resorcinarene-cholesterol columnar liquid crystals: Synthesis, mesomorphism and the influence of spacers on liquid crystalline behaviors

Novel calix[4]resorcinarene derivatives with four cholesterol units bridging by soft spacers or rigid Schiff-base spacers were prepared in yields of 63–76%. The hexagonal columnar liquid crystalline behaviors were firstly observed for calix[4]resorcinarene derivatives. The mesomorphic properties were influenced greatly by the structures of spacers. The rigid spacers were favorable for enhancing the phase transition temperatures and enlarging the temperature scopes of mesophase.

Naphthalene-cholesterol conjugate as simple gelator for selective sensing of CN– ion

Cholesterol-based Schiff base 1 has been designed and synthesised. The Schiff base 1 forms yellow coloured gel in DMF:H2O (2:1, v/v) and the gel is anion responsive. Among different anions, the gel phase of 1 is selectively transformed into sol in the presence of CN– ions and validates its visual sensing. 1H NMR, FTIR and HRMS spectroscopic techniques were adopted to study the gelation of 1 and its responsive behaviour towards anions.

Diaminomalenonitrile-decorated cholesterol-based supramolecular gelator: aggregation, multiple analyte (hydrazine, Hg2+ and Cu2+) detection and dye adsorption

A low molecular weight gelator (LMWG) containing a diaminomalenonitrile functional group 1 has been designed and synthesized. The compound forms supramolecular gels from DMF-H2O and 1,2-dichlorobenzene. The morphology of the gels reveals fibrous networks. The rheological study demonstrates that the DMF-H2O gel is stable and robust than the gel obtained from 1,2-dichlorobenzene, which is due to the existence of strong intermolecular forces among the gelators in DMF-H2O. The analysis of tan?δ values from the frequency sweep (tan?δ = G′′av/G′av) indicates that the DMF-H2O gel exhibits higher mechanical strength (lower tan?δ) than the 1,2-dichlorobenzene gel. The DMF-H2O gel has been explored for sensing and dye adsorption. The gel is established to be selective for visual recognition of hydrazine, Hg2+ and Cu2+ ions. Moreover, the gel exhibits excellent efficacy towards rapid and selective adsorption of cationic dyes from water (1 min).

Coumarin-based supramolecular gelator: A case of selective detection of F- and HP2O73-

Coumarin appended 1,2,3-triazole coupled cholesterol 1 which acts as a small molecular gelator has been designed and synthesized. Compound 1 has been noted to form gel from CHCl3-petroleum ether (1: 1, v/v). The stable gel is anion responsive. The gel state is transformed into the sol state selectively in the presence of F- and hydrogen pyrophosphate and thus validates their visual sensing over a series of other anions. Fluorescence study in CH3CN containing 0.5% DMSO also reveals substantial change in emission of 1 upon addition of both F- and hydrogen pyrophosphate and distinguishes them from other anions studied.

Novel liquid crystals with high fluorescence: Synthesis, mesomorphic and photophysical properties of cholesterol-triazine-BODIPY trimers

By step-by-step etherification on cyanuric chloride with BODIPY unit and cholesterol units, two novel cholesterol-triazine-BODIPY trimers (compounds 6 and 7 with one and two cholesterol unit, respectively) were designed and synthesized in high yields. The investigation on mesomorphic properties suggested that compound 6 with one cholesterol unit was a nematic liquid crystal but compound 7 with two cholesterol units was a hexagonal columnar liquid crystal. Both compounds 6 and 7 exhibited the strong fluorescence with high quantum yields and larger Stokes shifts than their precursors. The cholesterol-triazine moiety played crucial role for producing liquid crystalline property and enhancing fluorescence.

Cholesterol linked benzothiazole: A versatile gelator for detection of picric acid and metal ions such as Ag+, Hg2+, Fe3+ and Al3+ under different conditions

Cholesterol-appended benzothiazole 1 has been designed and synthesized. Compound 1 exhibits gelation in different solvents. The benzothiazole and cholesteryl motifs play a pivotal role in aggregation in organic solvents involving π-stacking and hydrophobic interactions, respectively. As an application, the nitrobenzene gel with good rheological properties has been noted to be useful in molecular recognition studies of multiple analytes ranging from neutral to ionic in nature. It selectively recognizes picric acid (PA) over a series of nitroaromatics by exhibiting a gel-to-sol phase transition with a distinguishable color change from pale yellow to deep yellow. On the other hand, the nitrobenzene gel shows selective recognition potential for Ag+ and Hg2+ ions through a gel-to-sol phase transition and the cations are distinguished by F-. The gelator 1 also reveals a measurable selective interaction with picric acid over a series of nitroaromatics in CH3CN containing 1% CHCl3. In CH3CN containing 1% CHCl3, compound 1 further shows affinity towards Fe3+, Al3+ and Hg2+ with distinctive features.

Cholesterol-Appended Benzimidazolium Salts: Synthesis, Aggregation, Sensing, Dye Adsorption, and Semiconducting Properties

A series of cholesterol-appended benzimidazolium salts 1-9 have been designed and synthesized. They have been explored in gel chemistry. The gelation of the benzimidazolium salts is dependent on the nature of the counteranions. In addition, the gelation behavior of the gelators is linked with the presence of both π-stacking and cholesteryl motifs. Whereas bisbenzimidazolium salt 2 forms a gel in dimethylsulfoxide/H2O (1:1, v/v) itself, under similar conditions, monobenzimidazolium salts 4 and 6 exhibit gelation in the presence of F- ions and validate the visual sensing of F-. As an application, the gel phase of 2 efficiently removes toxic dyes from waste water. Furthermore, all gels show thermally activated semiconducting property within a wide voltage window.

Preliminary Evaluation of Artemisinin–Cholesterol Conjugates as Potential Drugs for the Treatment of Intractable Forms of Malaria and Tuberculosis

To evaluate the feasibility of developing drugs that may be active against both malaria and tuberculosis (TB) by using in part putative cholesterol transporters in the causative pathogens and through enhancement of passive diffusion in granulomatous TB, artemisinin–cholesterol conjugates were synthesized by connecting the component molecules through various linkers. The compounds were screened in vitro against Plasmodium falciparum (Pf) and Mycobacterium tuberculosis (Mtb). Antimalarial activities (IC50) against Pf drug-sensitive NF54, and drug-resistant K1 and W2 strains ranged from 0.03–2.6, 0.03–1.9, and 0.02–1.7 μm. Although the compounds are less active than the precursor artemisinin derivatives, the cholesterol moiety renders the compounds relatively insoluble in the culture medium, and variation in solubilities among the different compounds may reflect in the range of efficacies observed. Activities against Mtb H37Rv were assessed using a standardized colony-forming unit (CFU) assay after 24 h pretreatment of cultures with each of the compounds. Percentage inhibition ranged from 3–38 % and 18–52 % at 10 and 80 μm, respectively. Thus, in contrast to the comparator drug artemether, the conjugates display enhanced activities. The immediate aims include the preparation of conjugates with enhanced aqueous solubilities, assays against malaria and TB in vivo, and for TB, assays using an infected macrophage model and assessment of granuloma influx.

A novel cholesterol conjugated fluorescence probe for Cu2+ detection and bioimaging in living cells

A cholesterol conjugated fluorescence probe T was designed and synthesized. The probe T can be used for recognition of Cu2+ by the absorption spectrum, fluorescence spectrum, and naked eyes respectively in aqueous solution. The cell imaging experiments showed that the probe has good membrane permeability and a huge potentiality for the detection of Cu2+ in living cells.

Selective sensing of Hg2+ via sol–gel transformation of a cholesterol-based compound

A cholesterol-based dithioacetal functionalised compound 1 has been designed, synthesised and successfully applied for the selective detection of Hg2+ ion. The specific Hg2+-induced deprotection of the thioacetal functionality of 1 resulted in sol-to-gel transition in DMF-H2O (1:1, v/v) via the formation of precursor aldehyde 3. This Hg2+-prompted rapid sol to gel conversion is insensitive to the nature of Hg2+-salt. In the study, other metal ions did not show any change. To the best of our knowledge, this is a first time report of a chemodosimeter that functions as a selective ‘naked-eye’ Hg2+-detector by showing in situ sol-to-gel conversion.