7alpha-Hydroxycholesterol

Base Information

• Chemical Name: 7alpha-Hydroxycholesterol
• CAS No.: 566-26-7
• Molecular Formula: C27H46 O2
• Molecular Weight: 402.661
• UNII: 95D0I22I0V
• DSSTox Substance ID: DTXSID40903965
• Nikkaji Number: J79.652B
• Wikipedia: 7%CE%B1-Hydroxycholesterol
• Wikidata: Q155744
• Pharos Ligand ID: MR7SMM82Y591
• Metabolomics Workbench ID: 34373
• ChEMBL ID: CHEMBL497207
• Mol file: 566-26-7.mol

Synonyms:7 alpha-hydroxycholesterol;7 beta-hydroxycholesterol;7alpha-hydroxycholesterol;7beta-hydroxycholesterol;cholest-5-en-3 beta,7 alpha-diol;cholest-5-en-3 beta,7 alpha-diol, (3beta)-isomer;cholest-5-en-3 beta,7 alpha-diol, (3beta,7alpha)-isomer, 14C-labeled;cholest-5-en-3 beta,7 alpha-diol, (3beta,7beta)-isomer;cholest-5-en-3beta,7beta-diol

Chemical Property of 7alpha-Hydroxycholesterol

Chemical Property:

• Vapor Pressure: 8.93E-13mmHg at 25°C
• Melting Point: 168-170°C
• Boiling Point: 515.3°Cat760mmHg
• PKA: 14.11±0.70(Predicted)
• Flash Point: 214.7°C
• PSA: 40.46000
• Density: 1.03g/cm³
• LogP: 6.35950
• Storage Temp.: Refrigerator
• Solubility.: Soluble in DMSO or in Ethanol.
• XLogP3: 7.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 402.349780706
• Heavy Atom Count: 29
• Complexity: 624

Purity/Quality:

99%, ^*data from raw suppliers

7α-HydroxyCholesterol ^*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(C=C4C3(CCC(C4)O)C)O)C
• Isomeric SMILES: C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H](C=C4[C@@]3(CC[C@@H](C4)O)C)O)C
• Description: 7α-Hydroxycholesterol (566-26-7) is a metabolite resulting from the action of cholesterol 7α-hydroxylase on cholesterol. 7α-Hydroxycholesterol is the first intermediate and a rate limiting step in the major pathway for bile acid synthesis in humans.??A pro-inflammatory mediator which upregulates production of CCL2 and MMP9 in macrophages and may promote progression of atherosclerosis.2,3?Possible biomarker for cellular lipid peroxidation.4
• Uses: Secondary metabolite of Cholesterol Secondary metabolite of Cholesterol.

Technology Process of 7alpha-Hydroxycholesterol

There total 63 articles about 7alpha-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: 80.0%

7-ketocholesteryl acetate (809-51-8) → (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)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 65 ℃; for 2h;

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

7-ketocholesteryl acetate

phthalic acid mono-(7α-hydroxy-cholest-5-en-3β-yl ester)

aluminum isopropoxide

Downstream raw materials:

cholesta-4,6-dien-3-one

Cholestanol

Coprostanol

3β,7α-dihydroxycholest-5-en-(25S)26-oic acid

Refernces

• 1、 Griffiths, William J.,Crick, Peter J.,Meljon, Anna,Theofilopoulos, Spyridon,Abdel-Khalik, Jonas,Yutuc, Eylan,Parker, Josie E.,Kelly, Diane E.,Kelly, Steven L.,Arenas, Ernest,Wang, Yuqin. "Additional pathways of sterol metabolism: Evidence from analysis of Cyp27a1?/? mouse brain and plasma". . p. 191 - 211. Retrieved 2019/01/03.
• 2、 Derewiaka,Molińska. "Cholesterol transformations during heat treatment". . p. 233 - 240. Retrieved 2015/01/09.