Acebrochol

Base Information

• Chemical Name: Acebrochol
• CAS No.: 514-50-1
• Molecular Formula: C29H48 Br2 O2
• Molecular Weight: 588.507
• UNII: 7XZB016MY5
• DSSTox Substance ID: DTXSID701023692
• Nikkaji Number: J501.472G
• Wikipedia: Acebrochol
• NCI Thesaurus Code: C77240
• ChEMBL ID: CHEMBL2104033
• Mol file: 514-50-1.mol

Synonyms:Acebrochol;514-50-1;Acebrocholum;Acebrocol;Acebrochol [INN:DCF];5,6beta-Dibromo-5alpha-cholestan-3beta-ol acetate;UNII-7XZB016MY5;7XZB016MY5;5,6-beta-Dibromo-5alpha-cholestan-3beta-ol acetate;5alpha,6beta-Dibromdihydrocholesterinacetat;5,6beta-Dibrom-5alpha-cholestan-3beta-ylacetat;ACEBROCHOL [INN];C29H48Br2O2;CHEMBL2104033;C29-H48-Br2-O2;DTXSID701023692;AKOS040745459;5alpha,6beta-Dibromocholestan-3beta-ol acetate;5.alpha.-Cholestan-3.beta.-ol, 5,6.beta.-dibromo-, acetate;5,6-.BETA.-DIBROMO-5.ALPHA.-CHOLESTAN-3.BETA.-OL ACETATE;Cholestan-3-ol, 5,6-dibromo-, acetate, (3.beta.,5.alpha.,6.beta.)-;(3S,5R,6R,8S,9S,10R,13R,14S,17R)-5,6-dibromo-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate;[(3S,5R,6R,8S,9S,10R,13R,14S,17R)-5,6-dibromo-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] acetate

Chemical Property of Acebrochol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 545.8°Cat760mmHg
• Flash Point: 283.9°C
• PSA: 26.30000
• Density: 1.27g/cm³
• LogP: 8.93030
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 10.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 588.20006
• Heavy Atom Count: 33
• Complexity: 724

Purity/Quality:

98%min ^*data from raw suppliers

CholesterylAcetateDibromide(MixtureofDiastereomers) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2CC(C4(C3(CCC(C4)OC(=O)C)C)Br)Br)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]([C@@]4([C@@]3(CC[C@@H](C4)OC(=O)C)C)Br)Br)C
• Uses: Cholesteryl Acetate Dibromide is an brominated intermediate in the synthesis of Cholesterol (C432501) derivatives.

Technology Process of Acebrochol

There total 15 articles about Acebrochol 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: 83.0%

Cholesteryl acetate (604-35-3) → 3β-acetoxy-5α,6β-dibromocholestane (514-50-1)

Guidance literature:

With tetraethylammonium bromide; In dichloromethane; at 20 ℃; for 0.5h; Electrochemical reaction;

DOI:10.1016/j.steroids.2005.06.002

Reference yield: 72.0%

Cholesteryl acetate (604-35-3) → 3β-acetoxy-5α,6β-dibromocholestane (514-50-1) + acetic acid-(5,6α-dibromo-5β-cholestan-3β-yl ester) (53224-97-8)

Guidance literature:

With bromine; potassium acetate; In diethyl ether; acetic acid; at 0 ℃; for 3h; Inert atmosphere;

DOI:10.3390/molecules27010225

Reference yield: 35.0%

Cholesteryl acetate (604-35-3) → 7α-hydroxycholest-5-en-3β-yl 3-acetate (19317-90-9) + 3β-acetoxy-5α,6β-dibromocholestane (514-50-1)

Guidance literature:

With N-Bromosuccinimide; In hexane; dichloromethane; for 2h; Product distribution; Heating; Irradiation; other conditions: addition of 8a or 16, other solvents, other times, other temperatures;

DOI:10.1016/S0040-4020(01)80888-7

upstream raw materials:

Cholesteryl acetate

5α,6β-dibromocholestan-3β-ol

acetyl chloride

N-bromoacetamide

Downstream raw materials:

Cholesteryl acetate

25-hydroxycholesteryl acetate

methyl 3β-acetoxychol-5-en-24-oate

3β-(toluene-4-sulfonyloxy)-chol-5-en-24-oic acid methyl ester

Refernces

• 1、 Milisavljevic, Smiljka S.,Wurst, Klaus,Laus, Gerhard,Vukicevic, Mirjana D.,Vukicevic, Rastko D.. "Electrochemical bromination of cholest-5-enes". . p. 867 - 872. Retrieved 2005.
• 2、 Doiuchi, Daiki,Fujii, Yui,Hirai, Go,Igawa, Kazunobu,Makino, Kana,Takeda, Daiki,Tomooka, Katsuhiko,Uchida, Tatsuya,Yoritate, Makoto. "Preparation of oxysterols by c–h oxidation of dibromocholestane with ru(Bpga) catalyst". supporting information. . Retrieved 2022/01/04.
• 3、 Kuang, Chunxiang,Yang, Qing,Senboku, Hisanori,Tokuda, Masao. "Rapid debromination of vic-dibromoalkanes with zinc powder in acetic acid under microwave irradiation". . p. 282 - 284. Retrieved 2007/10/03.