25-Hydroxycholest-5-en-3beta-yl acetate

Base Information

• Chemical Name: 25-Hydroxycholest-5-en-3beta-yl acetate
• CAS No.: 10525-22-1
• Molecular Formula: C29H48 O3
• Molecular Weight: 444.698
• European Community (EC) Number: 234-080-5
• Nikkaji Number: J212.457B
• ChEMBL ID: CHEMBL2442171
• Mol file: 10525-22-1.mol

Synonyms:EINECS 234-080-5;10525-22-1;25-Hydroxycholest-5-en-3beta-yl acetate;25-hydroxycholesterol acetate;CHEMBL2442171;SCHEMBL10784914;NSC 226103;Cholest-5-ene-3beta,25-diol 3-acetate;[(3S,8S,9S,10R,13R,14S,17R)-17-[(1R)-5-hydroxy-1,5-dimethyl-hexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate

Chemical Property of 25-Hydroxycholest-5-en-3beta-yl acetate

Chemical Property:

• Boiling Point: 523.8°Cat760mmHg
• Flash Point: 192.5°C
• PSA: 46.53000
• Density: 1.04g/cm³
• LogP: 7.07440
• XLogP3: 7.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 444.36034539
• Heavy Atom Count: 32
• Complexity: 739

Purity/Quality:

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCCC(C)(C)O)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)OC(=O)C)C)C
• Isomeric SMILES: C[C@H](CCCC(C)(C)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)OC(=O)C)C)C

Technology Process of 25-Hydroxycholest-5-en-3beta-yl acetate

There total 22 articles about 25-Hydroxycholest-5-en-3beta-yl acetate 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%

25-hydroxychlolesterol (2140-46-7) + acetic anhydride (108-24-7) → 25-hydroxycholesteryl acetate (10525-22-1)

Guidance literature:

With dmap; triethylamine; In tetrahydrofuran; at 20 ℃; for 20h;

DOI:10.1002/ejoc.200600394

Reference yield: 97.0%

Acetic acid (3S,8R,9S,10R,13S,14S)-17-((E)-(R)-5-hydroxy-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester (81393-45-5) → 25-hydroxycholesteryl acetate (10525-22-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 0.266667h; under 760 Torr;

DOI:10.1016/S0040-4039(01)83005-7

Reference yield: 93.0%

5α,6β-dibromo-25-hydroxycholestan-3β-yl acetate (142948-03-6) → 25-hydroxycholesteryl acetate (10525-22-1)

Guidance literature:

With acetic acid; zinc;

DOI:10.1021/jo00045a004

upstream raw materials:

25-hydroxychlolesterol

acetic anhydride

Acetic acid (3S,8R,9S,10R,13S,14S)-17-((E)-(R)-5-hydroxy-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

5α,6β-dibromo-25-hydroxycholestan-3β-yl acetate

Downstream raw materials:

demosterol

Cholesteryl acetate

25-hydroxychlolesterol

Refernces

• 1、 Riediker, Martin,Schwartz, Jeffrey. "A NEW SYNTHESIS OF 25-HYDROXYCHOLESTEROL". . p. 4655 - 4658. Retrieved 1981.
• 2、 Beuchet,Dherbomez,Elkiel,Charles,Letourneux. "Synthesis of 25-aminosterols, new antifungal agents". . p. 1599 - 1600. Retrieved 1999.
• 3、 Ogawa, Shoujiro,Kakiyama, Genta,Muto, Akina,Hosoda, Atsuko,Mitamura, Kuniko,Ikegawa, Shigeo,Hofmann, Alan F.,Iida, Takashi. "A facile synthesis of C-24 and C-25 oxysterols by in situ generated ethyl(trifluoromethyl)dioxirane". . p. 81 - 87. Retrieved 2009.
• 4、 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.
• 5、 -. "Composition for preventing or treating X-linked adrenoleukodystrophy comprising 25-hydroxycholesterol or its derivative". Paragraph 0100-0105. . Retrieved 2020/09/01.