7-Dehydrocholesterol acetate

Base Information

• Chemical Name: 7-Dehydrocholesterol acetate
• CAS No.: 1059-86-5
• Molecular Formula: C29H46 O2
• Molecular Weight: 426.683
• European Community (EC) Number: 213-896-5
• DSSTox Substance ID: DTXSID50909817
• Nikkaji Number: J28.120D
• Mol file: 1059-86-5.mol

Synonyms:cholesta-5,7-dien-3-yl acetate;cholesta-5,7-dien-3beta-yl acetate

Chemical Property of 7-Dehydrocholesterol acetate

Chemical Property:

• Melting Point: 129.5°C
• Refractive Index: 1.5045 (estimate)
• Boiling Point: 482.07°C (rough estimate)
• Flash Point: 256.3oC
• PSA: 26.30000
• Density: 1.0041 (rough estimate)
• LogP: 7.87960
• XLogP3: 8.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 426.349780706
• Heavy Atom Count: 31
• Complexity: 746

Purity/Quality:

99% ^*data from raw suppliers

7,8-DidehydrocholesterolAcetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2=CC=C4C3(CCC(C4)OC(=O)C)C)C
• Isomeric SMILES: C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3C2=CC=C4[C@@]3(CC[C@@H](C4)OC(=O)C)C)C
• Uses: 7,8-Didehydrocholesterol Acetate is an intermediate in the synthesis of Zymostenol, which is the derivative of Zymosterol (Z701520), an sterol intermediate in the biosynthesis of cholesterol (C432501).

Technology Process of 7-Dehydrocholesterol acetate

There total 36 articles about 7-Dehydrocholesterol 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: 87.0%

3-β-acetoxycholest-5-en-7-one tosylhydrazone (54201-67-1) → 7-Dehydrocholesteryl acetate (1059-86-5)

Guidance literature:

With lithium hydride; In toluene; at 120 ℃; for 8h; Large scale;

Reference yield: 86.0%

C36H53N2O4S(1-)*Li(1+) → 7-Dehydrocholesteryl acetate (1059-86-5)

Guidance literature:

In chlorobenzene; at 132 ℃; for 4h; Temperature;

Reference yield: 85.5%

Cholesteryl acetate (604-35-3) → 7-Dehydrocholesteryl acetate (1059-86-5)

Guidance literature:

With N-Bromosuccinimide; In tetrachloromethane; at 85 ℃; for 4h;

DOI:10.1039/c6md00344c

upstream raw materials:

tetrachloromethane

N-Bromosuccinimide

Cholesteryl acetate

chloroform

Downstream raw materials:

5α-cholest-7-ene-3β-ol acetate

5α-cholest-8-en-3β-ol

cholesta-5,8(9)-dien-3β-ol

7-dehydrocholesterol

Refernces

• 1、 Bernstein et al.. "-". . p. 433,437, 443. Retrieved 1949.
• 2、 Bide et al.. "-". . p. 1783,1787. Retrieved 1948.
• 3、 Ning, Yuhan,Tian, Hailong,Gui, Jinghan. "Biogenesis-Guided Synthesis and Structural Revision of Sarocladione Enabled by Ruthenium-Catalyzed Endoperoxide Fragmentation". . p. 11222 - 11226. Retrieved 2021.
• 4、 Milas,Heggie. "-". . p. 984. Retrieved 1938.
• 5、 Yamaguchi, Yoshihiro,Nakanishi, Yukio,Shimokawa, Teruyuki,Hashiguchi, Shigeru,Hayashi, Akira. "Structure Elucidation of Oxygenated Sterols from Eggs of Sea Hare, Aplysia juliana". . p. 1713 - 1714. Retrieved 1992.
• 6、 -. "PREPARATION OF 7-DEHYDROCHOLESTEROL USING SPECIFIC AROMATIC SOLVENTS". . . Retrieved 2021/10/30.