10525-22-1

Basic information

• Product Name: 25-hydroxycholest-5-en-3beta-yl acetate
• Synonyms: 25-hydroxycholest-5-en-3beta-yl acetate;Cholest-5-ene-3β,25-diol 3-acetate;Einecs 234-080-5
• CAS NO: 10525-22-1
• Molecular Formula: C₂₉H₄₈O₃
• Molecular Weight: 444.68962
• EINECS: 234-080-5
• Mol File: 10525-22-1.mol

Chemical Properties

• Boiling Point: 523.8°Cat760mmHg
• Flash Point: 192.5°C
• Appearance: /
• Density: 1.04g/cm³
• CAS DataBase Reference: 25-hydroxycholest-5-en-3beta-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 25-hydroxycholest-5-en-3beta-yl acetate(10525-22-1)
• EPA Substance Registry System: 25-hydroxycholest-5-en-3beta-yl acetate(10525-22-1)

Safety Data

• Hazardous Substances Data: 10525-22-1(Hazardous Substances Data)

Usage

Uses

Used in Scientific Research:
25-hydroxycholest-5-en-3beta-yl acetate is used as a research compound for studying the biosynthesis and metabolism of steroid hormones, bile acid, and vitamin D. Its role in these processes makes it a valuable tool for understanding the underlying mechanisms and pathways involved in these biological systems.
Used in Pharmaceutical Development:
25-hydroxycholest-5-en-3beta-yl acetate is used as a starting material or intermediate in the synthesis of various pharmaceutical compounds, particularly those related to hormone therapy and the treatment of conditions associated with hormonal imbalances. Its metabolic conversion to other steroid hormones makes it a potentially useful component in the development of new drugs.
Used in Diagnostic Applications:
25-hydroxycholest-5-en-3beta-yl acetate can be used as a marker or indicator in diagnostic tests for various conditions related to steroid hormone imbalances, bile acid metabolism, or vitamin D deficiency. Its presence and levels in biological samples can provide valuable information about an individual's health status and the effectiveness of treatment interventions.
Used in Nutritional Supplements:
25-hydroxycholest-5-en-3beta-yl acetate may be used as an ingredient in nutritional supplements designed to support healthy hormone levels, bile acid metabolism, and vitamin D synthesis. Its role in these processes suggests that it could potentially offer benefits to individuals with specific health concerns or those seeking to maintain optimal health. However, it is important to note that the safety and efficacy of such supplements should be thoroughly researched and validated before use.

Upstream product

• 2140-46-7 25-hydroxychlolesterol 
• 108-24-7 acetic anhydride 
• 81393-45-5 Acetic acid (3S,8R,9S,10R,13S,14S)-17-((E)-(R)-5-hydroxy-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 142948-03-6 5α,6β-dibromo-25-hydroxycholestan-3β-yl acetate 
• 64-19-7 acetic acid 
• 53139-49-4 6β-methoxy-3α,5-cyclocholestan-25-ol 
• 2665-04-5 demosterol acetate 
• 604-35-3 Cholesteryl acetate 
• 514-50-1 3β-acetoxy-5α,6β-dibromocholestane 
• 590-37-4 2-methylpent-4-yn-2-ol 
• 55461-50-2 24-dehydrocholesterol benzoate 
• 313-04-2 demosterol 
• 53139-50-7 6β-Methoxy-25-<(tetrahydropyran-2yl)oxy>-3β,5-cyclo-5α-cholestan 
• 3090-76-4 3-β-acetyloxy-17-ethenylidenandrost-5-ene 

Downstream Products

• 2140-46-7 25-hydroxychlolesterol 
• 313-04-2 demosterol 
• 604-35-3 Cholesteryl acetate 

Relevant articles and documents

GPR183-oxysterol axis in spinal cord contributes to neuropathic pain

Neuropathic pain is a debilitating public health concern for which novel non-narcotic therapeutic targets are desperately needed. Using unbiased transcriptomic screening of the dorsal horn spinal cord after nerve injury we have identified that Gpr183 (Epstein-Barr virus-induced gene 2) is upregulated after chronic constriction injury (CCI) in rats. GPR183 is a chemotactic receptor known for its role in the maturation of B cells, and the endogenous ligand is the oxysterol 7a,25-dihydrox-ycholesterol (7a,25-OHC). The role of GPR183 in the central nervous system is not well characterized, and its role in pain is unknown. The profile of commercially available probes for GPR183 limits their use as pharmacological tools to dissect the roles of this receptor in pathophysiological settings. Using in silico modeling, we have screened a library of 5 million compounds to identify several novel small-molecule antagonists of GPR183 with nanomolar potency. These compounds are able to antagonize 7a,25-OHC-induced calcium mobilization in vitro with IC50 values below 50 nM. In vivo intrathecal injections of these antagonists during peak pain after CCI surgery reversed allodynia in male and female mice. Acute intrathecal injection of the GPR183 ligand 7a,25-OHC in na?ve mice induced dose-dependent allodynia. Importantly, this effect was blocked using our novel GPR183 antagonists, suggesting spinal GPR183 activation as pronociceptive. These studies are the first to reveal a role for GPR183 in neuropathic pain and identify this receptor as a potential target for therapeutic intervention. SIGNIFICANCE STATEMENT We have identified several novel GPR183 antagonists with nanomolar potency. Using these antagonists, we have demonstrated that GPR183 signaling in the spinal cord is pronociceptive. These studies are the first to reveal a role for GPR183 in neuropathic pain and identify it as a potential target for therapeutic intervention.

A NEW SYNTHESIS OF 25-HYDROXYCHOLESTEROL

A simple (η3-allyl)palladium-based synthesis of 25-hydroxycholesterol is described using a dimetallated coupling reagent.

Oxidation of Natural Targets by Dioxiranes. 2. Direct Hydroxylation at the Side-Chain C-25 of Cholestane Derivatives and of Vitamin D3 Windaus-Grundmann Ketone

The direct, high-yield oxyfunctionalization of the side-chain C-25 of 5α-cholestan-3-one, 3β-acetoxy-5α-cholestane, and 5α,6β-Br2-3β-acetoxycholestane as well as of the vitamin D3-derived Windaus-Grundmann ketone has been achieved under mild conditions employing either dimethyldioxirane or its trifluoromethyl analogue.

Synthesis of 25-aminosterols, new antifungal agents

25-aminolanostenol 1 and 25-aminoeholesterol 2 were hemisynthesized from natural sterols and tested in vitro against Candida albicans. The biological activity of compound 1 was rather weak, whereas 2 exhibited in vitro antifungal activity with MIC value of 4 μM.

Inhibitory effect of oxygenated cholestan-3-ol derivatives on the growth of Mycobacterium tuberculosis

A variety of cholestan-3-ol derivatives, which are oxygenated at different positions of the steroid ring system, were prepared and tested for their inhibition of the Mycobacterium tuberculosis H37Rv strain. Several compounds showed significant antitubercular activities with MIC90 values in the range 4-8 μM and low or non-detectable toxicity against mammalian cells.

A facile synthesis of C-24 and C-25 oxysterols by in situ generated ethyl(trifluoromethyl)dioxirane

Experiments were performed to compare the regioselective hydroxylation of the isopropyl C-H bond at C-25 in 5α-cholestan-3β-yl acetate by in situ generated dimethyldioxirane, methyl(trifluoromethyl)dioxirane, hexafluoro(dimethyl)dioxirane or ethyl(trifluoromethyl)dioxirane (ETDO). The dioxiranes were generated from the corresponding ketones and potassium peroxymonosulfate in aq. NaHCO3, pH 7.5-8.0. Of the four dioxiranes examined, partially fluorinated, sterically bulky ETDO displayed the highest reactivity and regioselectivity. Using in situ generated ETDO, a facile, synthesis was developed for two naturally occurring oxysterols, i.e., 25-hydroxycholesterol, as well as its 3-sulfate (overall yield of the sulfate, 24%) and 24-oxocholesterol (16%), starting from cholesterol.

Preparation of oxysterols by c–h oxidation of dibromocholestane with ru(Bpga) catalyst

Seven mono-and dihydroxycholesterols were prepared by direct C–H oxidation of the cholestane skeleton with a recently developed Ru(Bpga) catalyst (Ru(Bpga) = [RuCl (bpga) (PPh3 )] Cl; bpga = 2-(bis(pyridin-2-ylmethyl)amino)-N-(2,6-dimethylphenyl)acetamide)). Due to the high selectivity of the Ru(Bpga) complex for tertiary C–H, the reaction afforded a mixture of 25-, 20-, 17-, and 14-oxygenated cholesterols that could be easily separated by high-performance liquid chromatography. These results suggest that late-stage C–H oxidation could be a viable strategy for preparing candidate metabolites of biologically important molecules.

GPR183 ANTAGONISTS FOR THE TREATMENT OF PAIN

Disclosed herein are compositions and methods for treating neuropathic pain in a subject in need thereof. Compositions disclosed herein are GPR183 antagonists. The methods include administering to a subject in need thereof a therapeutically effective amount of a GPR183 antagonist.

Composition for preventing or treating X-linked adrenoleukodystrophy comprising 25-hydroxycholesterol or its derivative

The present invention relates to a composition for treating X-linked adrenoleukodystrophy comprising 25-hydrocholesterol or a derivative thereof as an effective component. As it is confirmed that a level of C26 : 0 is effectively decreased in oligodendrocytes differentiated from CCALD cells, AMN cells and X-ALD patientandprime;s iPS cells, which are treated with the 25-hydrocholesterol (25-HC) or the derivative thereof, the present invention provides a pharmaceutical composition and a health food for preventing or treating X-linked adrenoleukodystrophy (X-ALD) comprising the 25-hydrocholesterol (25-HC) or the derivative thereof as an effective component.COPYRIGHT KIPO 2020

Detection of sulfate group transferase activity of the compound and its application haematoglobin

The invention discloses a heterozygous compound for detecting the activity of SULT (sulfotransferase) and application thereof. The general molecular formula of the heterozygous compound is shown in a formula (I) (in the Specification): X-L-H, wherein the H is a hormone or hydroxylated cholesterol part; the X is a micro-molecular group which can be identified by antibodies; the L is a connection part enabling the groups of the X part and the H part to be connected. The invention provides a detection and analysis method which is high in sensitivity, excellent in reproducibility, convenient for taking materials, simple and easy to operate and high in safety, and can quickly detect the activity of SULT in a sample. The invention provides the method in which the heterozygote of the hormone or hydroxylated cholesterol is taken as an enzyme substrate, and the level of the enzyme substrate subjected to sulfation is detected through an immunoassay to determine the activity of the SULT in a detected sample.