27-Hydroxycholesterol

Base Information

• Chemical Name: 27-Hydroxycholesterol
• CAS No.: 20380-11-4
• Molecular Formula: C₂₇H₄₆O₂
• Molecular Weight: 402.661
• UNII: 6T2NA6P5SQ
• DSSTox Substance ID: DTXSID40864941
• Nikkaji Number: J82.958G
• Wikipedia: 27-Hydroxycholesterol
• Wikidata: Q15634124
• NCI Thesaurus Code: C123794
• Pharos Ligand ID: MXUHNKURA7G7
• Metabolomics Workbench ID: 34395
• ChEMBL ID: CHEMBL353882
• Mol file: 20380-11-4.mol

Synonyms:(25R)-26-hydroxycholesterol;(25R)-cholest-5-ene-3 beta,26-diol;(3 beta,25R)-cholest-5-ene-3,26-diol;26-hydroxycholesterol, (25R);27-hydroxycholesterol;5-cholestene-3 beta,27-diol;cholest-5-ene-3 beta,26-diol, (25R)-;cholest-5-ene-3 beta,27-diol

Chemical Property of 27-Hydroxycholesterol

Chemical Property:

• Vapor Pressure: 7.43E-13mmHg at 25°C
• Melting Point: 172-174 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• Refractive Index: 1.537
• Boiling Point: 517.1 °C at 760 mmHg
• PKA: 15.03±0.70(Predicted)
• Flash Point: 215.6 °C
• PSA: 40.46000
• Density: 1.03 g/cm³
• LogP: 6.36110
• Storage Temp.: -20°
• Solubility.: Soluble in DMSO (up to 10 mg/ml) or in Ethanol (up to 10 mg/ml).
• XLogP3: 7.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 402.349780706
• Heavy Atom Count: 29
• Complexity: 612

Purity/Quality:

99.5% ^*data from raw suppliers

27 OHC ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)CO
• Isomeric SMILES: C[C@H](CCC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)CO
• Description: 27-Hydroxycholesterol (27-HC) is an endogenous oxysterol with multiple biological functions, including activity as a selective estrogen receptor modulator (SERM) (a mixed, tissue-specific agonist-antagonist of the estrogen receptor (ER)) and as an agonist of the liver X receptor (LXR). It is a metabolite of cholesterol that is produced by the enzyme CYP27A1. A link between high cholesterol and breast cancer has been identified, and it has been proposed that this is due to 27-HC production by CYP27A1. Because of its estrogenic action, 27-HC stimulates the growth of ER-positive breast cancer cells, and has been implicated in limiting the effectiveness of aromatase inhibitors in the treatment of breast cancer. As such, identified CYP27A1 inhibitors, including the marketed drugs anastrozole, fadrozole, bicalutamide, dexmedetomidine, ravuconazole, and posaconazole, have been proposed as potential adjuvant therapies in ER-positive breast cancer.www.abbexa.com/human-27-hydroxycholesterol-elisa-kit
• Uses: The liver x receptors (LXRα and LXRβ) are nuclear hormone receptors whose native ligands, oxysterols, induce the expression of genes involved in cholesterol and fatty acid metabolism. 27-hydroxy Cholesterol, a sterol 27-hydroxylase-mediated cholesterol hydroxylation product, activates LXRα and LXRβ in vitro with EC50 values of 85 and 71 nM, respectively, and is a potent suppressor of cholesterol biosynthesis. 25(R)-27-hydroxy Cholesterol is the more predominant-occurring (~80%) stereoisomer of the endogenous oxysterol 27-hydroxy cholesterol.[Cayman Chemical]

Technology Process of 27-Hydroxycholesterol

There total 102 articles about 27-Hydroxycholesterol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

3β,26-dibezoyloxycholest-5-ene-16β-ol mesylate (79045-93-5) → (25R)-cholest-5-ene-3β,26-diol (13095-61-9,13095-71-1,56845-83-1,80695-35-8,96553-74-1,96553-75-2,20380-11-4,26259-77-8)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; Heating;

DOI:10.1016/S0040-4020(01)92435-4

Reference yield: 96.0%

(20R,25R)-cholest-5-ene-3β,26-diol 3,26-diacetate (43204-21-3) → (25R)-cholest-5-ene-3β,26-diol (13095-61-9,13095-71-1,56845-83-1,80695-35-8,96553-74-1,96553-75-2,20380-11-4,26259-77-8)

Guidance literature:

With potassium carbonate; In methanol; for 1h; Heating;

DOI:10.1021/jo00213a031

Reference yield: 90.0%

(25S)-26-ethoxymethoxycholesterol (114683-28-2) → (25R)-cholest-5-ene-3β,26-diol (13095-61-9,13095-71-1,20380-11-4,80695-35-8,96553-74-1,96553-75-2,56845-83-1,26259-77-8)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; for 3h; Heating;

DOI:10.1039/P19870001749

upstream raw materials:

kryptogenin

(25R)-26-hydroxy-16-oxocholesterol

(20R,25R)-cholest-5-ene-3β,26-diol 3,26-diacetate

(2R,6R)-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-1-ol

Downstream raw materials:

(25R)-cholest-5-ene-3β,26-diol

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

(25S)-3-keto-5α-cholest-7-en-26-oic acid

(25S)-3-acetoxy-26-tosyloxycholest-5-ene

Refernces

• 1、 -. "PEPTIDES". Page/Page column 25; 26. . Retrieved 2016/06/14.
• 2、 Saini, Ratni,Boland, Sebastian,Kataeva, Olga,Schmidt, Arndt W.,Kurzchalia, Teymuras V.,Kn?lker, Hans-Joachim. "Stereoselective synthesis and hormonal activity of novel dafachronic acids and naturally occurring steroids isolated from corals". scheme or table. p. 4159 - 4163. Retrieved 2012/07/14.