Podophyllotoxin acetate

Base Information

• Chemical Name: Podophyllotoxin acetate
• CAS No.: 1180-34-3
• Molecular Formula: C24H24 O9
• Molecular Weight: 456.449
• NSC Number: 36408
• UNII: 2KJY6T7ZX5
• DSSTox Substance ID: DTXSID90151999
• Nikkaji Number: J556.521I
• Wikidata: Q83018553
• Metabolomics Workbench ID: 123453
• ChEMBL ID: CHEMBL1409147
• Mol file: 1180-34-3.mol

Synonyms:podophyllotoxin acetate

Chemical Property of Podophyllotoxin acetate

Chemical Property:

• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 456.14203234
• Heavy Atom Count: 33
• Complexity: 729

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1C2COC(=O)C2C(C3=CC4=C(C=C13)OCO4)C5=CC(=C(C(=C5)OC)OC)OC
• Isomeric SMILES: CC(=O)O[C@@H]1[C@H]2COC(=O)[C@@H]2[C@@H](C3=CC4=C(C=C13)OCO4)C5=CC(=C(C(=C5)OC)OC)OC

Technology Process of Podophyllotoxin acetate

There total 10 articles about Podophyllotoxin 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: 90.0%

acetic acid (64-19-7,77671-22-8) + podofilox (518-28-5) → podophyllotoxinyl acetate (1180-34-3)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃;

DOI:10.1080/10286020.2018.1490275

Reference yield: 80.0%

acetyl chloride (75-36-5) + podofilox (518-28-5) → podophyllotoxinyl acetate (1180-34-3)

Guidance literature:

In pyridine; benzene; Ambient temperature;

DOI:10.1002/jps.2600721012

Reference yield: 73.0%

acetic anhydride (108-24-7) + podofilox (518-28-5) → podophyllotoxinyl acetate (1180-34-3)

Guidance literature:

With 1H-imidazole; dmap; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1002/anie.202104682

upstream raw materials:

acetic anhydride

epipodophyllotoxin

podofilox

acetyl chloride

Downstream raw materials:

podophyllotoxone

(5aR,8aS,9R)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione

Acetic acid (5R,5aR,8aR,9R)-9-(3,4-dihydroxy-5-methoxy-phenyl)-8-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl ester

Acetic acid (5R,5aR,8aR,9R)-9-(3,4-diacetoxy-5-methoxy-phenyl)-8-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl ester

Refernces

• 1、 Miyazawa, Mitsuo,Fukuyama, Mami,Yoshio, Kimio,Kato, Takenori,Ishikawa, Yukio. "Biologically active components against Drosophila melanogaster from Podophyllum hexandrum". . p. 5108 - 5110. Retrieved 1999.
• 2、 Che, Zhi-Ping,Tian, Yue-E,Liu, Sheng-Ming,Jiang, Jia,Hu, Mei,Chen, Gen-Qiang. "Stereoselective synthesis of 4β-acyloxypodophyllotoxin derivatives as insecticidal agents". . p. 1028 - 1041. Retrieved 2018/07/15.