20380-11-4

Usage

Uses

Used in Pharmaceutical Industry:
5,25R-Cholesten-3beta,26-diol is used as a potential therapeutic target for the development of drugs to treat breast cancer. It has been implicated in limiting the effectiveness of aromatase inhibitors in the treatment of breast cancer, and its production by the enzyme CYP27A1 has been linked to a high cholesterol and breast cancer connection.
Used in Research Applications:
5,25R-Cholesten-3beta,26-diol is used as a research tool to study its inhibitory effect on hepatic lipid accumulation, as a liver X receptor (LXR) ligand in breast cancer cell lines, and as a control in liquid chromatography with tandem mass spectrometry (LC-MS-MS) for the quantitation of 25-OHC in jejunum samples.
Used in Cholesterol and Fatty Acid Metabolism:
5,25R-Cholesten-3beta,26-diol is used as a ligand for liver X receptors (LXRα and LXRβ), which are nuclear hormone receptors that induce the expression of genes involved in cholesterol and fatty acid metabolism. It activates LXRα and LXRβ in vitro with EC50 values of 85 and 71 nM, respectively, and is a potent suppressor of cholesterol biosynthesis.
Used in Bile Synthesis:
5,25R-Cholesten-3beta,26-diol is used as a substrate for bile synthesis, playing a crucial role in the regulation of cholesterol homeostasis in the body.

Mode of action

27-Hydroxycholesterol is an endogenous metabolite of cholesterol produced by the hydroxylation of the carbon at position 27 by the enzyme sterol 26-hydroxylase, mitochondrial (CYP27A1). Some neoplasms produce excess of 27-hydroxycholesterol (27HC) or inhibit its catabolism, and high cholesterol levels are correlated with elevated levels of 27HC; under these conditions, 27HC may have deleterious selective estrogen receptor modulator (SERM) and liver X receptor (LXR) agonistic activities. As a SERM, 27HC binds to and prevents the activation of estrogen receptors (ERs) in the vasculature. This prevents ER-mediated vasodilation and abrogates the cardiovascular protective effects of estrogen. However, 27HC binds to and activates ERs and LXRs in breast tissue, which stimulates ER-dependent breast cancer cell growth and metastasis.pubchem.ncbi.nlm.nih.gov/compound/27-Hydroxycholesterol

References

1) Heverin et al. (2004), Changes in the levels of cerebral and extracerebral sterols in the brains of patients with Alzheimer's disease; J. Lipid Res.,?45?1862) Shafaati et al. (2011), Marked accumulation of 27-hydroxycholesterol in the brains of Alzheimer's patients with the Swedish APP 670-671 mutation; J. Lipid Res.,?52?10043) Umetani et al. (2007), 27-Hydroxycholesterol is an endogenous SERM that inhibits the cardiovascular effects of estrogen; Nature Medicine,?13?11854) Fu et al. (2001), 27-Hydroxycholesterol is an endogenous ligand for liver X receptor in cholesterol-loaded cells; J. Biol.Chem.,?276?38378

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

Upstream product

• 77611-30-4 (25R)-26-hydroxy-16-oxocholesterol 
• 43204-21-3 (20R,25R)-cholest-5-ene-3β,26-diol 3,26-diacetate 
• 51231-28-8 (3R)-3-((3S,10R,13R,17R)-10,13-dimethyl-3-((tetrahydro-2H-pyran-2-yl)oxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)butanal 
• 35961-41-2 1-((3S,10R,13S,17S)-10,13-dimethyl-3-((tetrahydro-2H-pyran-2-yl)oxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone 
• 79190-29-7 (3S,8S,9S,10R,13R,14S,17R)-17-((1R,5S)-6-tert-Butoxy-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol 
• 96481-07-1 (25S)-3β,26-dihydroxycholest-5-en-16-one 
• 869858-24-2 (25S)-cholest-5-en-3β,26-diol 26-(2'-tetrahydropyranyl) ether 
• 470-05-3 diosgenin 
• 1061-54-7 yamogenin-acetate 
• 114683-20-4 6β-ethoxy-3α,5-cyclo-5α-23,24-dinorcholan-22-ol 
• 114683-22-6 6β-ethoxy-22-iodo-3α,5-cyclo-5α-23,24-dinorcholane 
• 113917-66-1 (25S)-3β,26-bis-p-nitrobenzoyloxycholest-5-en-16β-ol 
• 113917-67-2 (25S)-3,26-bis-p-nitrobenzoylcholest-5-en-16-one 
• 1097641-33-2 (25S)-3β-(tert-butyldimethylsilyloxy)-26-(pivaloyloxy)cholest-5-ene 

Downstream Products

• 13095-61-9 (25R)-cholest-5-ene-3β,26-diol 
• 113917-70-7 C₄₇H₆₀F₆O₆ 
• 71472-91-8 (25R)-5-Cholesten-3β,26-diol-26-tosylat 
• 894357-60-9 2,2-Dimethyl-propionic acid (2R,6R)-6-{(3R,5S,8R,9S,10S,13R,14S,17R)-3-[2-(4-benzoyl-phenyl)-acetoxy]-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl}-2-methyl-heptyl ester 
• 949004-12-0 (25S)-3-keto-5α-cholest-7-en-26-oic acid 
• 113917-72-9 (25S)-3-acetoxy-26-tosyloxycholest-5-ene 
• 105078-98-6 (25S)-3β-acetoxy-26-trityloxycholest-5-ene 
• 113917-68-3 C₄₇H₆₀F₆O₆ 
• 113917-68-3 C₄₇H₆₀F₆O₆ 
• 481-21-0 cholestane 
• 105078-99-7 3-O-acetyl-26-hydroxy-26-O-tosylcholesterol 
• 192187-67-0 (25R)-7α,26-dihydroxycholest-4-en-3-one 
• 306288-45-9 (25R)-cholest-5-ene-3β,7α,26-triol 3β,26-dibenzoate 
• 306288-42-6 (25R)-7-oxocholest-5-en-3β,26-diyl dibenzoate 

Relevant academic research and scientific papers

Synthesis of side-chain oxysterols and their enantiomers through cross-metathesis reactions of Δ22 steroids

A synthetic route that utilizes a cross-metathesis reaction with Δ22 steroids has been developed to prepare sterols with varying C-27 side-chains. Natural sterols containing hydroxyl groups at the 25 and (25R)-26 positions were prepared. Enantiomers of cholesterol and (3β,25R)-26-hydroxycholesterol (27-hydroxycholesterol) trideuterated at C-19 were prepared for future biological studies.

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.

Stereoselective synthesis and hormonal activity of novel dafachronic acids and naturally occurring steroids isolated from corals

A stereoselective synthesis of (25S)-Δ1-, (25S)-Δ1,4-, (25S)-Δ1,7-, (25S)- Δ8(14)-, (25S)-Δ4,6,8(14)-dafachronic acid, methyl (25S)-Δ1,4-dafachronate and (25S)-5α-hydroxy-3,6- dioxocholest-7-en-26-oic acid is described. (25S)-Δ1,4- Dafachronic acid and its methyl ester are natural products isolated from corals and have been obtained by synthesis for the first time. (25S)-5α-Hydroxy- 3,6-dioxocholest-7-en-26-oic acid represents a promising synthetic precursor for cytotoxic marine steroids.

Synthesis and biological activity of the (25R)-cholesten-26-oic acids - Ligands for the hormonal receptor DAF-12 in Caenorhabditis elegans

We describe the stereoselective transformation of diosgenin (4a) to (25R)-Δ4-dafachronic acid (1a), (25R)-Δ7- dafachronic acid (2a), and (25R)-cholestenoic acid (3a), which represent potential ligands for the hormonal receptor DAF-12

Synthesis and hormonal activity of the (25s)-cholesten-26-oic acids -potent ligands for the daf-12 receptor in caenorhabditis elegans

Using a highly stereoselective Evans aldol reaction for the introduction of the stereogenic center at C-25, we describe an efficient synthesis of the orthogonally diprotected (25S)-26-hydroxycholesterol 11. In a few synthetic steps, this crucial intermediate 11 has been converted into the four (25S)-cholesten-26-oic acids 1-4, which have been obtained in 12-15 steps and 19-53% overall yield based on commercially available 3p-hydroxychol-5-en-24-oic acid (5). Our biological studies of the compounds 1-4 reveal that (25S)-Δ7-dafachronic acid (1) represents the most active steroidal ligand for the hormonal receptor DAF-12 in Caenorhabditis elegans. Moreover, the saturated (25S)-dafachronic acid (3) represents a new ligand for this receptor and the (25S)-steroidal acids are more active as compared to their corresponding (25R)-counterparts.

Stereoselective synthesis of (25r)-dafachronic acids and (25R)-cholestenoic acid as potential ligands for the DAF-12 receptor in Caenorhabditis elegans

Commercially available diosgenin has been used as starting material for a highly efficient synthesis of (25R)-dafachronic acids and (25R)-cholestenoic acid, potential ligands for the receptor DAF-12 in the nematode Caenorhabditis elegans.

Stereoselective synthesis of the hormonally active (25S)- Δ7-dafachronic acid, (25S)-Δ4-dafachronic acid, (25S)-dafachronic acid, and (25S)-cholestenoic acid

We report a stereoselective synthesis of the (25S)-cholestenoic-26-acids which are highly efficient ligands for the hormonal receptor DAF-12 in Caenorhabditis elegans.

Synthesis of the aglycone of the shark repellent pavoninin-4 using remote functionalization

The aglycone of shark repellent pavoninin-4, (25R)-5α-cholestan- 3α,15α,26-triol 26-acetate 1a, was synthesized from (25R)-cholest-5-en-3β,-26-diol 4 (26-hydroxycholesterol) in eight steps in 18% overall yield. Breslow's remote functionalization strategy

Preparation of (25R)- and (25S)-26-functionalized steroids as tools for biosynthetic studies of cholic acids

A new synthesis of both epimeric forms of 26-cholestanoic acids and 26-alcohols containing a 3β-hydroxy-Δ5- or a Δ4-3-keto-functionality in ring A is described starting from stigmasterol or (20S)-3β-acetoxy-pregn-5-en-20-carboxylic a