Cholesterol beta-epoxide

Base Information

• Chemical Name: Cholesterol beta-epoxide
• CAS No.: 4025-59-6
• Molecular Formula: C₂₇H₄₆O₂
• Molecular Weight: 402.661
• UNII: PFD65A4X36
• DSSTox Substance ID: DTXSID501314152
• Nikkaji Number: J362.555I
• Wikipedia: Oxycholesterol
• Wikidata: Q7115899
• Metabolomics Workbench ID: 34370
• ChEMBL ID: CHEMBL497439
• Mol file: 4025-59-6.mol

Synonyms:5,6-epoxycholesterol;5alpha,6alpha-epoxycholesterol;5beta,6beta-epoxycholesterol

Chemical Property of Cholesterol beta-epoxide

Chemical Property:

• Vapor Pressure: 5.43E-12mmHg at 25°C
• Boiling Point: 497.7°Cat760mmHg
• Flash Point: 200.9°C
• PSA: 32.76000
• Density: 1.04g/cm³
• LogP: 6.59990
• XLogP3: 8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 402.349780706
• Heavy Atom Count: 29
• Complexity: 630

Purity/Quality:

99% ^*data from raw suppliers

Cholesterol5beta,6beta-Epoxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-48/20/21/22-68/20/21/22
• Safety Statements: 7-36/37

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2CC4C5(C3(CCC(C5)O)C)O4)C
• Isomeric SMILES: C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C[C@@H]4[C@]5([C@@]3(CC[C@@H](C5)O)C)O4)C
• Uses: Cholesterol 5beta,6beta-epoxide is an oxysterol produced as an oxidation product of cholesterol.

Technology Process of Cholesterol beta-epoxide

There total 66 articles about Cholesterol beta-epoxide 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: 72.7%

cholesterol (57-88-5) + tert-butyl alcohol (75-65-0) → 5ξ,6ξ-epidioxy-6ξ-tert-butoxy-5,6-secocholestane-3β,5ξ-diol (84681-03-8) + 5beta,6beta-Epoxycholestanol (2953-38-0,4025-59-6,24116-45-8,55700-78-2,75764-48-6,97100-48-6,114246-94-5,134356-45-9,1250-95-9) + 5α,6α-epoxycholestan-3β-ol (1250-95-9)

Guidance literature:

With ozone; for 0.25h; Yields of byproduct given; Ambient temperature;

DOI:10.1021/ja00345a052

Reference yield: 64.0%

cholesterol (57-88-5) → 5beta,6beta-Epoxycholestanol (2953-38-0,4025-59-6,24116-45-8,55700-78-2,75764-48-6,97100-48-6,114246-94-5,134356-45-9,1250-95-9) + 5α,6α-epoxycholestan-3β-ol (1250-95-9)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In benzene; for 24h; Ambient temperature;

Reference yield: 64.0%

cholesterol (57-88-5) → 6α,7α-epoxy-5α-cholestane-3β,5α-diol (114862-91-8) + 5beta,6beta-Epoxycholestanol (2953-38-0,4025-59-6,24116-45-8,55700-78-2,75764-48-6,97100-48-6,114246-94-5,134356-45-9,1250-95-9) + 5α,6α-epoxycholestan-3β-ol (1250-95-9) + 5α,6α-epoxy-5α-cholestane-3β,7α-diol (62107-20-4)

Guidance literature:

With titanium(IV) isopropylate; oxygen; In pyridine; at 0 ℃; for 12h; Yield given. Title compound not separated from byproducts; Irradiation;

upstream raw materials:

Perbenzoic acid

chloroform

cholesterol

(3S,5R,6R,8S,9S,10R,13R,14S,17R)-5-bromo-6-hydroxy-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate

Downstream raw materials:

5β,6β-epoxy-cholestan-3β-ol benzoate

3β-acetoxy-6-phenyl-cholest-5-ene

acetic acid-(6β-hydroxy-6α-phenyl-5α-cholestanyl-(3β)-ester)

cholestanetriol

Refernces

• 1、 Verhoog, Stefan,Brooks, Allen F.,Winton, Wade P.,Viglianti, Benjamin L.,Sanford, Melanie S.,Scott, Peter J.H.. "Ring opening of epoxides with [18F]FeF species to produce [18F]fluorohydrin PET imaging agents". supporting information. p. 6361 - 6364. Retrieved 2019/06/07.
• 2、 Soto-Castro, Delia,Lara Contreras, Roberto Carlos,Pina-Canseco, María,Santillán, Rosa,Hernández-Huerta, María Teresa,Negrón Silva, Guillermo E.,Pérez-Campos, Eduardo,Rincón, Susana. "Solvent-free synthesis of 6β-phenylamino-cholestan-3β,5α-diol and (25R)-6β-phenylaminospirostan-3β,5α-diol as potential antiproliferative agents". supporting information. p. 92 - 100. Retrieved 2017/09/19.