17954-98-2

Usage

Uses

Used in Cellular and Metabolic Studies:
22(R)-Hydroxycholesterol is used as a research tool for studying the effects on the production of free radicals and in studies related to fatty acid metabolism in bovine aortic endothelial cells.
Used in Chemokine Receptor Inhibition:
22(R)-Hydroxycholesterol is used as an inhibitor of chemokine receptor activity, which can be relevant for various biological and medical applications.
Used in Cholesterol Transport and Absorption:
22(R)-Hydroxycholesterol, acting through LXR heterodimerized with the retinoid X receptor, induces the expression of the ABCA1 reverse cholesterol transporter. This activity increases the efflux of cholesterol from enterocytes and thus inhibits the overall absorption of cholesterol, making it potentially useful in the treatment of atherosclerosis and other cholesterol-related conditions.
Used in Drug Development:
22(R)-Hydroxycholesterol can be used as an endogenous positive control for testing LXR agonists, which have potential as therapeutic agents for the treatment of atherosclerosis and other diseases associated with cholesterol metabolism dysregulation.

Biochem/physiol Actions

22(R)-hydroxycholesterol (22(R)-HC) is a liver X receptor (LXR) ligand.. 22(R)-HC in combination with other oxysterols promote mesenchymal stem cell osteogenesis. It regulates cholesterol homeostasis. Low levels of 22(R)-HC is observed in Alzheimer′s disease and it may be implicated in neuroinflammation and neurodegenerative diseases. 22(R)-hydroxycholesterol also suppresses prostate tumor progression.

InChI:InChI=1/C27H46O2/c1-17(2)7-6-8-18(3)22-11-12-23-21-10-9-19-15-20(28)16-25(29)27(19,5)24(21)13-14-26(22,23)4/h9,17-18,20-25,28-29H,6-8,10-16H2,1-5H3/t18-,20-,21+,22-,23+,24+,25?,26-,27+/m1/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 
• 54548-85-5 (20(22)E)-cholesta-5,20(22)-dien-3β-ol acetate 
• 5674-02-2 2-methylpropylmagnesium chloride 
• 54604-91-0 (22R)-22,23-epoxy-6β-methoxy-3α,5-cyclo-5α-24-norcholane 
• 56784-70-4 (2R,5R,6S)-6-[(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]-2-methyl-5-(tetrahydro-pyran-2-yloxy)-heptanal 
• 107-82-4 i-pentyl bromide 
• 57-88-5 cholesterol 
• 76719-23-8 (22E)-cholest-5,22-diene-3β-tetrahydropyranyloxy-26-oic acid ethyl ester 
• 70813-70-6 22(R)-hydroxy-3α,5-cyclo-6β-methoxy-5α-cholane-23(E)-ene 
• 54604-94-3 (22S)-22,23-epoxy-6β-methoxy-3α,5-cyclo-5α-24-norcholane 
• 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 

Downstream Products

• 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 
• 17955-01-0 (22S)-22-hydroxycholesterol dibenzoate 
• 20117-31-1 3β,22β_F-bis-benzoyloxy-5α-cholestane 
• 62698-12-8 3β-benzoyloxy-cholesta-5,20(22)t-diene 
• 481-21-0 cholestane 
• 145-13-1 Pregnenolone 
• 15234-55-6 (22R)-20α,22-dihydroxycholesterol 
• 17955-00-9 3β,22β_F-bis-benzoyloxy-cholest-5-ene 
• 19243-30-2 22-ketocholesterol 

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.

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

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.

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.

SYNTHESES OF FOUR ISOMERS OF 25-HYDROXYVITAMIN D3-26,23-LACTONE

A major metabolite of vitamin D3 was recently isolated and identified as 25-hydroxyvitamin D3-26,23-lactone.To determine the configurations at C-23 and C-25 positions, the four stereoisomers were synthesized by stereoselective lactonization method.The two 23R-isomers were obtained by iodolactonization of 22,23-trans-26-acid, and the two 23S-isomers were synthesized by selenolactonization of 22,23-cis-26-acid.The four synthetic isomers and the naturally produced lactone were co-chromatographed on a high performance liquid chromatographic system capable of separating the four isomers.The natural lactone comigrated with synthetic (23S,25R)-isomer determining its structure as (23S,25R)-25-hydroxyvitamin D3-26,23-lactone.

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.