3b-Hydroxycholest-5-en-7-one

Base Information

• Chemical Name: 3b-Hydroxycholest-5-en-7-one
• CAS No.: 566-28-9
• Molecular Formula: C27H44 O2
• Molecular Weight: 400.645
• Metabolomics Workbench ID: 165298
• Mol file: 566-28-9.mol

Synonyms:Cholest-5-en-3b-ol-7-one;3b-hydroxycholest-5-en-7-one;delta5-Cholesten-3b-ol-7-one

Chemical Property of 3b-Hydroxycholest-5-en-7-one

Chemical Property:

• Vapor Pressure: 7.76E-13mmHg at 25°C
• Melting Point: 158-160°C
• Refractive Index: 1.4480 (estimate)
• Boiling Point: 516.7°Cat760mmHg
• PKA: 14.68±0.70(Predicted)
• Flash Point: 218.5°C
• PSA: 37.30000
• Density: 1.03g/cm³
• LogP: 6.56770
• Storage Temp.: Refrigerator
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 7.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 400.334130642
• Heavy Atom Count: 29
• Complexity: 663

Purity/Quality:

98%,99%, ^*data from raw suppliers

7-KetoCholesterol(~98%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2C(=O)C=C4C3(CCC(C4)O)C)C
• Isomeric SMILES: C[C@H](CCCC(C)C)C1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C(=O)C=C4[C@@]3(CCC(C4)O)C)C
• Description: 7-keto Cholesterol is a bioactive sterol and a major oxysterol component of oxidized LDL. It is produced by oxidation of cholesterol via ethanol-mediated lipid peroxidation or photodamage as well as oxidation of 7-dehydro cholesterol by the cytochrome P450 (CYP) isoform CYP7A1. 7-keto Cholesterol inhibits CYP7A1 (IC50 = ~1 μM). It induces activation and chemotaxis of retinal microglia as well as polarization to a pro-inflammatory state via NLRP3 inflammasome activation in vitro. Intraocular implantation of 7-keto cholesterol coated wafers increases ocular levels of VEGF, IL-1β, and GRO/KC, macrophage infiltration, and neovascularization in rat eye. Levels of 7-keto cholesterol in lipid deposits are increased in a variety of chronic diseases, including atherosclerosis, Alzheimer''s disease, and age-related macular degeneration.
• Uses: 5-Cholesten-3β-ol-7-one was used as a standard in the determination of cholesterol derivatives by GC-MS and HPLC. A metabolite of Cholesterol

Technology Process of 3b-Hydroxycholest-5-en-7-one

There total 32 articles about 3b-Hydroxycholest-5-en-7-one 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: 53.0%

cholesterol (57-88-5) → 7-Oxocholesterol (566-28-9) + cholest-5-en-3β,7β-diol (566-27-8)

Guidance literature:

With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide; In dichloromethane; at 23 ℃; for 48h; Time; Temperature; chemoselective reaction; Catalytic behavior;

DOI:10.1002/asia.201800256

Reference yield: 30.0%

tert.-butylhydroperoxide (75-91-2) + cholesterol (57-88-5) → 7-Oxocholesterol (566-28-9) + 3β-hydroxycholest-5-ene-7α-hydroperoxide (36871-91-7,75671-16-8,75671-17-9,86900-29-0,2846-29-9) + (3S,7S,8S,9S,10R,13R,14S,17R)-17-((R)-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]phenanthrene-3,7-diol (566-26-7) + cholest-5-en-3β,7β-diol (566-27-8) + 7β-hydroperoxy-3β-hydroxycholest-5-ene (36871-91-7)

Guidance literature:

Rh₂(cap)4; In dichloromethane; at 25 ℃; for 15h;

Reference yield: 30.0%

cholesterol (57-88-5) → 7-Oxocholesterol (566-28-9) + 3β-hydroxycholest-5-ene-7α-hydroperoxide (36871-91-7,75671-16-8,75671-17-9,86900-29-0,2846-29-9) + (3S,7S,8S,9S,10R,13R,14S,17R)-17-((R)-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]phenanthrene-3,7-diol (566-26-7) + cholest-5-en-3β,7β-diol (566-27-8) + 7β-hydroperoxy-3β-hydroxycholest-5-ene (36871-91-7)

Guidance literature:

With tert.-butylhydroperoxide; [Rh₂(cap)4*2CH₃CN]; In water; 1,2-dichloro-ethane; at 25 ℃; for 15h;

DOI:10.1021/jo8021132

upstream raw materials:

cholesterol

cholesterol

3β-hydroxycholest-5-ene-7α-hydroperoxide

tert.-butylhydroperoxide

Downstream raw materials:

cholest-5-en-3β,7β-diol

cholest-3,5-dien-7-one

2-Iodo-7-oxo-4-nor-2,3-secocholest-5-en-3-yl formate

3α,5-cyclo-5α-cholestan-7-one

Refernces

• 1、 Lam, Ying-Pong,Yeung, Ying-Yeung. "Metal-Free Allylic Oxidation of Steroids Using TBAI/TBHP Organocatalytic Protocol". supporting information. p. 2369 - 2372. Retrieved 2018/04/19.
• 2、 Xu, Guihua,Liu, Donghong,Zhao, Gongling,Chen, Shiguo,Wang, Jun,Ye, Xingqian. "Effect of Eleven Antioxidants in Inhibiting Thermal Oxidation of Cholesterol". . p. 215 - 225. Retrieved 2016/02/03.