2140-46-7

Basic information

• Product Name: 25-HYDROXYCHOLESTEROL
• Synonyms: 25-HYDROXYCHOLESTEROL;3BETA,25-DIHYDROXY-5-CHOLESTENE;5-CHOLESTEN-3-BETA, 25-DIOL;5-CHOLESTENE-3BETA,25-DIOL;25-Hydroxycholesterol (not deuterated);Cholest-5-ene-3,25-diol, (3.beta.)-;5-cholestene-3β,25-diol;(3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-6-hydroxy-6-methyl-heptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS NO: 2140-46-7
• Molecular Formula: C₂₇H₄₆O₂
• Molecular Weight: 402.65
• Product Categories: Hydroxycholesterol;Apoptosis;Inhibitors;Intermediates & Fine Chemicals;Metabolites & IMpurities;Pharmaceuticals;Steroids
• Mol File: 2140-46-7.mol
• Article Data: 37

Chemical Properties

• Melting Point: 177-179 °C
• Boiling Point: 513.1 °C at 760 mmHg
• Flash Point: 213.5 °C
• Appearance: /
• Density: 1.03g/cm³
• Vapor Pressure: 1.13E-12mmHg at 25°C
• Refractive Index: 1.538
• Storage Temp.: -20°C
• Solubility: chloroform: 50 mg/mL, clear, colorless to slightly yellow
• PKA: 15.03±0.70(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
• Merck: 13,4846
• BRN: 3161259
• CAS DataBase Reference: 25-HYDROXYCHOLESTEROL(CAS DataBase Reference)
• NIST Chemistry Reference: 25-HYDROXYCHOLESTEROL(2140-46-7)
• EPA Substance Registry System: 25-HYDROXYCHOLESTEROL(2140-46-7)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-48
• Safety Statements: 26-36-45
• WGK Germany: 3
• Hazardous Substances Data: 2140-46-7(Hazardous Substances Data)

Usage

Description

25-Hydroxy Cholesterol, an oxysterol, is an oxygenated derivative of cholesterol (C432501). It is formed from cholesterol by cholesterol-25-hydroxylase, and its production can be induced by inflammation or infection. This off-white solid suppresses endogenous cholesterol synthesis by binding to insulin-induced gene (INSIG) proteins and preventing sterol regulatory element binding proteins (SREBPs) from being transported to the Golgi.
Used in Antiviral Applications:
25-Hydroxy Cholesterol is used as an antiviral agent for inhibiting the replication of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) in Vero cells. It reduces viral RNA loads in the lung and trachea in a mouse model of SARS-CoV-2 infection when administered at a dose of 100 mg/kg per day.
Used in Immunomodulation:
25-Hydroxy Cholesterol is used as an immunomodulator for suppressing IgA class switching induced by LPS and various cytokines in B cells (IC50 = ~50 nM). It also induces apoptosis in human monocytic cell lines and CEM cells, associated with negative regulation of c-Myc.
Used in Ophthalmology:
25-Hydroxy Cholesterol is used in ophthalmology for reversing cataracts in mice. It has been shown to improve cataract severity by at least one grade in mice with age-related and hereditary cataracts after 4 weeks of treatment.
Used in Research:
25-Hydroxy Cholesterol is used in research for studying the activation of macrophage toll-like receptor (TLR) by microbial antigens, which induces the synthesis of this oxysterol. It has been used to treat mouse neuroblastoma cells to activate the ABCA1 signaling and in studies related to fatty acid metabolism.
Used in HIV Treatment:
25-Hydroxy Cholesterol is used as an inhibitor of human immunodeficiency virus (HIV) replication in vitro, providing a potential therapeutic approach for managing the virus.

Biochem/physiol Actions

25-Hydroxycholesterol is a side-chain oxysterol that reportedly triggers activation of a number of cholesterol molecules. This triggers their movement from cell membrane to the endoplasmic reticulum (ER). 25-Hydroxycholesterol affects the immune system and has a key role in the pathogenesis of atherosclerosis.

Purification Methods

25-Hydroxycholesterol forms colourless needles from MeOH [Schwartz Tetrahedron Lett 22 4655 1981]. The 3
acetoxy derivative has m 142-142.8o (from Me2CO) and [] D -40.4o (c 2, CHCl3). The 3,25-diacetoxy derivative has m 119-120.5o (from MeOH) and [] 25D -35.5o (CHCl3). [Dauben & Bradlow J Am Chem Soc 72 4248 1950, Ryer et al. J Am Chem Soc 72 4247 1950, Beilstein 6 IV 6437.]

References

1) Diczialusy (2013),?On the formation and possible biological role of 25-hydroxcholesterol; Biochimie,?95?455 2) McDonald and Russell (2010),?25-hydroxycholesterol: a new life in immunology: J. Leuko. Biol.?88?1071

InChI:InChI=1/C27H46O2/c1-18(7-6-14-25(2,3)29)22-10-11-23-21-9-8-19-17-20(28)12-15-26(19,4)24(21)13-16-27(22,23)5/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t18-,20+,21+,22-,23-,24-,26+,27-/m1/s1

Upstream product

• 917-64-6 methyl magnesium iodide 
• 7494-34-0 27-nor-5-cholesten-3β-ol-25-one 
• 7548-94-9 3β-acetoxy-27-norcholest-5-en-25-one 
• 23357-13-3 methyl 3-acetoxy-23a-homo-5-cholen-24-oate 
• 57-88-5 cholesterol 
• 59975-17-6 3β,25-diacetoxycholest-5-ene 
• 917-54-4 methyllithium 
• 10525-22-1 25-hydroxycholesteryl acetate 
• 75-16-1 methylmagnesium bromide 
• 55064-27-2 cholest-5-ene-3β,25-diol 3-tetrahydropyran-2-yl ether 
• 55064-27-2 6-[(3S,8S,9S,10R,13R,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-heptan-2-ol 
• 142886-27-9 3β-(tert-butyldimethylsiloxy)cholest-5-en-25-ol 
• 53139-50-7 6β-Methoxy-25-<(tetrahydropyran-2yl)oxy>-3β,5-cyclo-5α-cholestan 
• 80239-48-1 25-(Tetrahydro-2H-pyran-2-yl)oxy-5-cholesten-3β-ol 

Downstream Products

• 19897-08-6 25-Hydroxycholest-4-en-3-one 
• 5255-15-2 5-cholen-3β-ol 
• 2665-04-5 demosterol acetate 
• 127619-29-8 N^α-<4-(25-Hydroxy-5-cholesten-3β-yloxy)succinyl>-N-glycinamid 
• 64164-45-0 25-fuoro-5-cholesten-3β-ol 
• 51297-13-3 25-Hydroxy-1,4,6-cholestatrien-3-on 
• 10525-22-1 25-hydroxycholesteryl acetate 
• 70706-33-1 5α-cholestane-3β,25-diol 
• 64164-61-0 cholest-5-ene-3β,25-diol 3β,25-dibenzoate 
• 64907-20-6 (3β)-3-(acetyloxy)-25-hydroxycholest-5-en-7-one 
• 913254-17-8 3β-acetoxy-7-keto-5α-cholestan-25-ol 
• 64907-22-8 [3H]-7alpha, 25-Dihydroxycholesterol 
• 306288-41-5 3β,25-dihydroxycholest-5-en-7-one 3β,25-dibenzoate 
• 306288-44-8 cholest-5-ene-3β,7α,25-triol 3β,25-dibenzoate 

Relevant articles and documents

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Enzymatic Regioselectivity in the Hydroxylation of Cholesterol Catalyzed by a Membrane-Spanning Metalloporphyrin

The hydroxylation of simple alkanes and the selective C-25 hydroxylation of cholesterol have been achieved with a membrane-spanning Mn(III) porphyrin positioned in a synthetic bilayer assembly by appended steroidal substituents.

A comparison of the potential unfavorable effects of oxycholesterol and oxyphytosterol in mice: Different effects, on cerebral 24S-hydroxychoelsterol and serum triacylglycerols levels

Sterol oxidation products derived from cholesterol and phytosterol are formed during the processing and storage of foods. The objective of the present study was to assess the potential unfavorable effects of oxysterols in mice. C57BL/6J mice were fed an AIN-93G-based diet containing 0.2 g/kg of oxycholesterol or oxyphytosterol for 4 weeks. The most abundant oxysterol in the diet was 7-ketosterol, but α-epoxycholesterol, β-epoxycholesterol, or 7α-hydroxyphytosterol, and 7β-hydroxyphytosterol were more prominent than 7-ketosterol in the serum and liver respectively. Consumption of both oxysterols resulted in an increased in 4β-hydroxycholesterol and total oxycholesterol in the liver, but the oxycholesterol-fed mice had a lower level of cerebral 24S-hydroxycholesterol and a higher level of the serum triacylglycerols than the control and oxyphytosterol groups. These results indicate that both oxysterols in the diet are accumulated in the body, but that the biological effect of oxycholesterol is different from that of oxyphytosterol.

Method for synthesizing and purifying 25-hydroxycholesterol

The invention belongs to the technical field of organic chemical synthesis and relates to a method for synthesizing and purifying 25-hydroxycholesterol. The method comprises the following steps that: (1) a mixture containing a compound as shown in a formula (I) and a compound as shown in a formula (II) contacts with an addition reagent, so that an addition product can be obtained, on the basis of the total weight of the mixture, the content of the compound as shown in the formula (I) is 10-60 wt%, the addition reagent has a structure as shown in a formula (III), in the formula (I) and the formula (II), R1 is H or C1-C4 acyl, in the formula (III), R2 is a C1-C4 acyl, and R1 and R2 are the same or different; (2) saponification reaction is carried out on the addition product and alkali to obtain a saponification product; and crystallization and separation are performed to obtain the 25-hydroxycholesterol. The method for preparing the 25-hydroxycholesterol has the advantages of easy-to-obtain raw materials and simple and safe process steps.

NOVEL METHOD FOR SYNTHESIZING 25-OH CHOLESTEROL/CALCIFEDIOL FROM PHYTOSTEROL

The present invention discloses novel method for synthesizing vegan 25-OH cholesterol/Calcifediol from inexpensive crude phytosterol. According to the method, Phytosterols are reacted to form corresponding i-steroid through tosylation and methanolysis. i-steroid on reductive ozonolysis to C-22 alcohol and conversion via C-22 tosylate to C-22 iodide in good yield. Coupling of C-22 tosylate with Grignard reagent of 4-bromo-2-methyl-2-[(trimethylsilyl)oxy] butane followed by deprotection yielded 25-OH cholesterol. In a process variant, nickel mediated conjugate addition of C-22 iodide to an electron deficient alkene ethyl acrylate and treating corresponding ester with methyl magnesium bromide as means of installing the side chain of 25-OH cholesterol in high yield. Further bromination reaction of 25-OH cholesterol diacetate followed by dehydrobromination using TBAF yielded 25-OH 7-dehydrocholesterol. Further photo reaction of 25-OH 7-dehydrocholesterol in to previtamin D3 using high or medium pressure mercury lamp and subsequent thermal reaction of previtamin D3 to 25-OH vitamin D3(Calcifediol) in good yield.