Ergosterol 5alpha,8alpha-epidioxide

Base Information

• Chemical Name: Ergosterol 5alpha,8alpha-epidioxide
• CAS No.: 2061-64-5
• Molecular Formula: C28H44 O3
• Molecular Weight: 428.656
• Mol file: 2061-64-5.mol

Synonyms:NSC 31324;Ergosterol 5.alpha.,8.alpha.-epidioxide;5a,8a-Peroxyergosterol;5.alpha.,8.alpha.-Ergosta-6,22-dien-3.beta.-ol, 5,8-epidioxy-;Ergosta-6,22-dien-3-ol, 5,8-epidioxy-, (3.beta.,5.alpha.,8.alpha.,22E)-;VXOZCESVZIRHCJ-BQYQJAHWSA-N;Ergosterol 5alpha ,8alpha -epidioxide;BS-1255;(-)-5alpha,8alpha-Epidioxyergosta-6,22-dien-3beta-ol;5,8-Epidioxy-5-.alpha.,8-.alpha.-ergosta-6,22-dien-3-.beta.-ol;5,8-Epidioxy-2H-cyclopenta[a]phenanthrene, ergosta-6,22-dien-3-ol deriv.;5.alpha.,8.alpha.-Epidioxy-24(R)-methylcholesta-6,22-dien-3.beta.-ol

Chemical Property of Ergosterol 5alpha,8alpha-epidioxide

Chemical Property:

• Vapor Pressure: 4.42E-12mmHg at 25°C
• Melting Point: 178 °C
• Boiling Point: 499.7°Cat760mmHg
• PKA: 14.97±0.70(Predicted)
• Flash Point: 256°C
• PSA: 38.69000
• Density: 1.08g/cm³
• LogP: 6.47360
• XLogP3: 6.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 428.32904526
• Heavy Atom Count: 31
• Complexity: 772

Purity/Quality:

98%min ^*data from raw suppliers

Ergosterol peroxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C)C=CC(C)C1CCC2C1(CCC3C24C=CC5(C3(CCC(C5)O)C)OO4)C
• Isomeric SMILES: CC(C)C(C)/C=C/C(C)C1CCC2C1(CCC3C24C=CC5(C3(CCC(C5)O)C)OO4)C
• Uses: Network pharmacology and molecular docking study on inhibition of Mpro, primary protease of COVID-19, by Poria cocos and its active compounds.

Technology Process of Ergosterol 5alpha,8alpha-epidioxide

There total 13 articles about Ergosterol 5alpha,8alpha-epidioxide 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: 93.0%

Ergosterol (57-87-4) → ergosterol peroxide (2061-64-5)

Guidance literature:

With oxygen; phloxine B; In methanol; at 5 ℃; for 3h; Irradiation; Inert atmosphere;

DOI:10.1039/c9ob00145j

Reference yield: 58.0%

C28H44O3 → sarocladione + ergosterol peroxide (2061-64-5)

Guidance literature:

With trifluoroacetic acid; In chloroform; at 20 ℃; for 168h; Reagent/catalyst; Solvent; Inert atmosphere;

DOI:10.1002/anie.202101451

Reference yield: 12.0%

Ergosterol (57-87-4) → ergosterol peroxide (2061-64-5) + 9,11-dehydroergosterol peroxide (86363-50-0)

Guidance literature:

With oxygen; methylene blue; Irradiation;

DOI:10.1248/cpb.50.1286

upstream raw materials:

Ergosterol

isopyrocalcyferyl acetate

Downstream raw materials:

ergosta-4,6,8(14),22-tetraen-3-one

Ergosterol

3β-acetoxy-5α-ergosta-7,22t-dien-5-ol

Refernces

• 1、 Ambrus, Gabor. "Novel 26-oxygenated products in microbial degradation of ergosterol". . p. 626 - 629. Retrieved 1995.
• 2、 Cantrell, Charles L.,Rajab, Mohamed S.,Franzblau, Scott G.,Fronczek, Frank R.,Fischer, Nikolaus H.. "Antimycobacterial ergosterol-5,8-endoperoxide from Ajuga remota". . p. 732 - 734. Retrieved 1999.
• 3、 Bu, Ming,Cao, Tingting,Li, Hongxia,Guo, Mingzhou,Yang, Burton B.,Zeng, Chengchu,Hu, Liming. "Synthesis of 5α,8α-Ergosterol Peroxide 3-Carbamate Derivatives and a Fluorescent Mitochondria-Targeting Conjugate for Enhanced Anticancer Activities". . p. 466 - 474. Retrieved 2017.
• 4、 Bu, Ming,Li, Hongling,Wang, Haijun,Wang, Jing,Lin, Yu,Ma, Yukun. "Synthesis of ergosterol peroxide conjugates as mitochondria targeting probes for enhanced anticancer activity". . . Retrieved 2019.
• 5、 Cateni, Francesca,Doljak, Bojan,Zacchigna, Marina,Anderluh, Marko,Piltaver, Andrej,Scialino, Giuditta,Banfi, Elena. "New biologically active epidioxysterols from Stereum hirsutum". . p. 6330 - 6334. Retrieved 2007.
• 6、 Shaker, Sharpkate,Sun, Ting-Ting,Wang, Liang-Yue,Ma, Wen-Zhe,Wu, Dong-Lan,Guo, Yong-Wei,Dong, Jun,Chen, Yan-Xiu,Zhu, Long-Ping,Yang, De-Po,Li, Hou-Jin,Lan, Wen-Jian. "Reactive oxygen species altering the metabolite profile of the marine-derived fungus Dichotomomyces cejpii F31-1". . p. 41 - 48. Retrieved 2019/07/03.
• 7、 -. "BIOLOGICALLY ACTIVE GANODERMA LUCIDUM COMPOUNDS AND SYNTHESIS OF ANTICANCER DERIVATIVES; ERGOSTEROL PEROXIDE PROBES FOR CELLULAR LOCALIZATION". Paragraph 000106; 000149. . Retrieved 2020/08/22.