Cytosporone B

Base Information

• Chemical Name: Cytosporone B
• CAS No.: 321661-62-5
• Molecular Formula: C18H26O5
• Molecular Weight: 322.39600
• European Community (EC) Number: 663-384-4
• DSSTox Substance ID: DTXSID80443557
• Nikkaji Number: J1.469.095F
• Wikidata: Q27076966
• Pharos Ligand ID: R5FWCKM4CC56
• Metabolomics Workbench ID: 107526
• ChEMBL ID: CHEMBL1221517
• Mol file: 321661-62-5.mol

Synonyms:Csn-B;cytosporone B

Chemical Property of Cytosporone B

Chemical Property:

• Boiling Point: 471.6±24.0 °C(Predicted)
• PKA: 7.54±0.40(Predicted)
• PSA: 83.83000
• Density: 1.126±0.06 g/cm3(Predicted)
• LogP: 3.74660
• Storage Temp.: ?20°C
• Solubility.: DMSO: >20mg/mL
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 11
• Exact Mass: 322.17802393
• Heavy Atom Count: 23
• Complexity: 368

Purity/Quality:

99% ^*data from raw suppliers

Cytosporone B ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCC(=O)C1=C(C=C(C=C1O)O)CC(=O)OCC
• Uses: Cytosporone B is a naturally occuring agonist for the nuclear receptor Nur77., induces the expression of Nur77-dependent genes including the gene for Nur77 itself. Induces apoptosis in cancer cells. Cytosporone B has been used:as a positive control and NR4A1 agonist in NR4A1 reporter gene assayfor Nr4a1 activationto treat OVX mice and study its effect on migration of osteoclast precursor

Technology Process of Cytosporone B

There total 17 articles about Cytosporone B 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: 95.0%

ethanol (64-17-5) + 2-(3,5-dihydroxy-2-octanoylphenyl)acetic acid → Cytosporone B (321661-62-5)

Guidance literature:

With sulfuric acid; at 20 ℃; for 1h;

DOI:10.1590/S0103-50532012000100018

Reference yield: 95.0%

ethyl 2-(3,5-bis(benzyloxy)-2-octanoylphenyl)acetate (1146977-69-6) → Cytosporone B (321661-62-5)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; for 4h;

DOI:10.1002/cjoc.201090163

Reference yield:

3,5-dihydroxy-2-(1'-oxoocta-2'E,4'E-dienyl)benzeneacetic acid ethyl ester (1004540-64-0) → Cytosporone B (321661-62-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 2h;

DOI:10.1021/np070504b

upstream raw materials:

3,5-dihydroxy-2-(1'-oxoocta-2'E,4'E-dienyl)benzeneacetic acid ethyl ester

ethyl 2-(3,5-bis(benzyloxy)-2-octanoylphenyl)acetate

ethanol

Octanoic acid

Refernces

• 1、 Xia, Zebin,Cao, Xihua,Rico-Bautista, Elizabeth,Yu, Jinghua,Chen, Liqun,Chen, Jiebo,Bobkov, Andrey,Wolf, Dieter A.,Zhang, Xiao-Kun,Dawson, Marcia I.. "Relative impact of 3- and 5-hydroxyl groups of cytosporone B on cancer cell viability". . p. 332 - 339. Retrieved 2013/06/04.
• 2、 Von Delius, Max,Le, Christine M.,Dong, Vy M.. "Rhodium-phosphoramidite catalyzed alkene hydroacylation: Mechanism and octaketide natural product synthesis". supporting information. p. 15022 - 15032. Retrieved 2012/11/06.