17711-16-9

Usage

Uses

Used in Pharmaceutical Applications:
22-Hydroxycholesterol is used as a therapeutic agent for modulating chemokine receptor activity. Its inhibitory effects on these receptors can be beneficial in treating conditions where chemokine receptor activity is dysregulated, such as in certain inflammatory diseases or immune disorders.
Used in Research Applications:
In the field of research, 22-hydroxycholesterol serves as an important tool for studying the role of cholesterol metabolism and its impact on various cellular processes. It can be used to investigate the mechanisms underlying chemokine receptor signaling and to identify potential targets for drug development.
Used in Drug Delivery Systems:
Similar to gallotannin, 22-hydroxycholesterol can also be incorporated into drug delivery systems to enhance its bioavailability and therapeutic efficacy. By employing various carriers such as organic or metallic nanoparticles, the delivery, solubility, and overall effectiveness of 22-hydroxycholesterol can be improved, allowing for more targeted and efficient treatment options.

InChI:InChI=1/C27H46O2/c1-17(2)6-11-25(29)18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20-,21-,22+,23-,24-,25?,26-,27+/m0/s1

Upstream product

• 76719-31-8 2-{(3S,8S,9S,10R,13S,14S,17R)-17-[1-((2S,3S)-3-Isobutyl-oxiranyl)-ethyl]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy}-tetrahydro-pyran 
• 76719-29-4 3-((2S,3S)-3-{1-[(3S,8S,9S,10R,13S,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]-ethyl}-oxiranyl)-2-methyl-propan-1-ol 
• 76719-30-7 2-((3S,8S,9S,10R,13S,14S,17R)-17-{1-[(2S,3S)-3-(3-Iodo-2-methyl-propyl)-oxiranyl]-ethyl}-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy)-tetrahydro-pyran 
• 76719-27-2 (S)-5-{(R)-2-[(3S,8S,9S,10R,13S,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]-1-iodo-propyl}-3-methyl-dihydro-furan-2-one 
• 76719-28-3 3-((2S,3S)-3-{1-[(3S,8S,9S,10R,13S,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]-ethyl}-oxiranyl)-2-methyl-propionic acid methyl ester 
• 5674-02-2 2-methylpropylmagnesium chloride 
• 54604-94-3 (22S)-22,23-epoxy-6β-methoxy-3α,5-cyclo-5α-24-norcholane 
• 128322-43-0 C₄₄H₇₀O₇SSi 
• 76976-75-5 (22R)-3β-tetrahydropyranyloxycholest-5-en-23-yn-22-ol 
• 60132-90-3 3β,20Z-cholesta-5,20(22)-diene-3-ol acetate 
• 22145-61-5 3β-(tetrahydropyran-2-yloxy)-23,24-dinorchol-5-en-22-al 
• 107-82-4 i-pentyl bromide 
• 57-88-5 cholesterol 
• 32277-72-8 3β-acetoxy-cholest-5-en-22-one 

Downstream Products

• 17955-01-0 (22S)-22-hydroxycholesterol dibenzoate 
• 54604-57-8 (22S)-cholest-5-ene-3β,22-diol 3β-acetate 
• 110536-30-6 22-fluoroprevitamin D₃ 
• 110536-31-7 22-fluorovitamin D₃ 
• 54548-85-5 (20(22)E)-cholesta-5,20(22)-dien-3β-ol acetate 

Relevant academic research and scientific papers

Regulation of liver X receptor target genes by 22-functionalized oxysterols. Synthesis, in silico and in vitro evaluations

The endogenous oxysterol 22(R)-hydroxycholesterol (22RHC, 1) is an LXR agonist which upregulates genes of critical involvement in human cholesterol- and lipid metabolism. In contrast, its synthetic epimer 22(S)-hydroxycholesterol (22SHC, 8) has shown specific antagonistic effects in recent studies, avoiding unwanted side effects provided by potent LXR agonists. In terms of LXR modulation, the aim of this study was to compare 22SHC (8), 22RHC (1) and synthesized ligands with keto- and amide functionality in the 22nd position of the cholesterol scaffold. 22SHC (8) and 22RHC (1) performed as expected while 22-ketocholesterol (22KC, 10) revealed an attractive in vitro profile for further investigation in terms of anti-atherosclerotic properties as selective upregulation of the ATP-binding cassette transporter ABCA1 was observed. A new synthesized amide derivate, Fernholtz cyclohexylamide (13) was shown to reduce lipogenesis in a dose-responsive manner and abolish the effect of the potent LXR agonist T0901317 when administered simultaneously.

Chirality Transfer in Stereoselective Synthesis. A Highly Stereocontrolled Synthesis of 22-Hydroxylated Steroid Side Chains via the -Wittig Rearrangement

An efficient approach toward 22-oxygenated steroid side chains has been accomplished utilizing the -Wittig rearrangement of the dianion derived from the (E)-17(20)-ethylidene-16α-(carboxymethyl)oxy steroid.

Cytotoxicity and suppression of immunoglobulin production against human Namalwa cells caused by oxidized cholesterol

The effects of oxidized cholesterols on proliferation and IgM production of human lymphoblastoid Namalwa cells were examined. An oxidized cholesterol mixture, in contrast to cholesterol, was a potent cytotoxin to Namalwa cells. Among oxidized cholesterols examined, 25-hydroxycholesterol was the most cytotoxic. However, no oxidized cholesterol examined suppressed IgM production, although cholestanetriol and 7-ketocholesterol did suppress it. Thus, oxidized cholesterols are cytotoxic to lymphocytes, while the influence on the immunoglobulin production may be marginal.

Stereocontrolled Synthesis of (22R)-22-Hydroxycholesterol Guided by α-Silyl Radical Stabilization

The synthesis of (22R)-22-hydroxycholesterol, featuring formation of three contiguous chiral centers (C-17, 20, and 22) in a single step by the use of a 6-endo α-silyl radical-mediated cyclization is presented.Additionally, an interesting protiodesilyatio

22-Hydroxycholesterol Derivatives as HMG CoA Reductase Suppressors and Serum Cholesterol Lowering Agents

A series of 22-hydroxycholesterol derivatives with a modified side chain terminus was prepared.These agents were evaluated in vitro and in vivo for their ability to suppress HMG CoA reductase, the rate-limiting enzyme of cholesterol biosynthesis.In tissue culture assays, 22-hydroxycholesterol as well as the side chain modified analogues were potent inhibitors of HMG CoA reductase.However, only those sterols with a modified side chain terminus were effective suppressors of liver reductase whene administered ig to rats. 22-Hydroxy-25-methylcholesterol (4a) and 25-fluoro-22-hydroxycholesterol (15a) significantly lowered serum cholesterol levels when administered ig to primates; 25-chloro-22-hydroxycholesterol (15b) and the analogue with a cyclopropyl terminus, 20b, were ineffective.The cholesterol-lowering sterols did not significantly alter lipoprotein levels; however, the two compounds have been shown to inhibit acyl-coenzyme A:cholesterol-transferase (ACAT) in tissue culture studies

Stereoselective Synthesis of Plant Growth-promoting Steroids, Brassinolide, Castasterone, Typhasterol, and Their 28-Nor Analogues

Plant growth-promoting steroids, brassinolide (1a), (22R,23R,24S)-2α,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-ergostan-6-one, castasterone (2a), (22R,23R,24S)-2α,3α,22,23-tetrahydroxy-5α-ergostan-6-one, 28-norbrassinolide (1b), (22R,23R)-2α,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-cholestan-6-one, brassinone (2b), (22R,23R)-2α,3α,22,23-tetrahydroxy-5α-cholestan-6-one, and typhasterol (2c), (22R,23R,24S)-3α,22,23-trihydroxy-5α-ergostan-6-one, have been stereoselectively synthesized.These steroids show very strong biological activities in three different kinds of bioassays.

Synthesis of Brassinolide, a Steroidal Lactone with Plant-growth Promoting Activity

Brassinolide, a plant-growth promoter isolated from rape pollen, was stereoselectively synthesized from dinorcholenic acid.