Podophyllotoxone

Base Information

• Chemical Name: Podophyllotoxone
• CAS No.: 477-49-6
• Molecular Formula: C₂₂H₂₀O₈
• Molecular Weight: 412.396
• Mol file: 477-49-6.mol

Synonyms:Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-5,8-dione,5a,6,8a,9-tetrahydro-9-(3,4,5-trimethoxyphenyl)-, [5aR-(5aa,8ab,9a)]-; Podophyllotoxone (6CI)

Chemical Property of Podophyllotoxone

Chemical Property:

• Melting Point: 191.73℃
• Boiling Point: 602.3±55.0 °C(Predicted)
• PSA: 89.52000
• Density: 1.365±0.06 g/cm3 (20 ºC 760 Torr)
• LogP: 2.55850

Purity/Quality:

≥98% ^*data from raw suppliers

Podophyllotoxone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Podophyllotoxone is a naturally occurring flavonoid that shown significant cell apoptosis and antiproliferative affect against human PC-3 and Bcap-37 cancer cell lines

Technology Process of Podophyllotoxone

There total 48 articles about Podophyllotoxone 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%

(5aR,8aR,9R)-5,8-Dioxo-9-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5a-carboxylic acid allyl ester (620116-57-6) → (1α,2α,3α)-podophyllotoxin (55515-07-6,477-48-5,477-49-6,60660-51-7,64550-42-1,64937-82-2,86594-36-7,130322-38-2)

Guidance literature:

With palladium diacetate; formic acid; triphenylphosphine; NEt₂; In tetrahydrofuran; at 25 ℃; for 0.716667h;

DOI:10.1021/ja0376588

Reference yield: 95.0%

(-)-4-desoxy-4-methylenepodophyllotoxin → podophyllotoxone (477-48-5,477-49-6,55515-07-6,60660-51-7,64550-42-1,64937-82-2,86594-36-7,130322-38-2)

Guidance literature:

(-)-4-desoxy-4-methylenepodophyllotoxin; With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In dichloromethane; at 20 ℃; for 4h;

With sodium periodate; In dichloromethane; for 0.5h;

DOI:10.1002/anie.200802611

Reference yield: 92.0%

podofilox (518-28-5) → podophyllotoxone (477-48-5,477-49-6,55515-07-6,60660-51-7,64550-42-1,64937-82-2,86594-36-7,130322-38-2)

Guidance literature:

With dipyridinium dichromate; In dichloromethane; at 0 - 20 ℃; for 3h;

DOI:10.1016/j.bmc.2014.07.031

upstream raw materials:

podofilox

podophyllotoxinyl acetate

podophyllotoxin-7′-O-β-D-glucopyranoside

deoxypodophyllotoxin

Downstream raw materials:

(1α,2α,3α)-podophyllotoxin

<5R-(5α,6α)>-5,6,7,8-tetrahydro-7-methylidene-8-oxo-5-(3,4,5-trimethoxyphenyl)naphtho<2,3-d><1,3>dioxole-6-carboxylic acid

(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

epipodophyllotoxin

Refernces

• 1、 Arseniyadis, Stellios,Clavier, Louis,Copin, Chloé,Fournier, Jean,Giffard, Jean-Fran?ois,Jean, Alexandre,Katsina, Tania,Macedo Portela Da Silva, Nayane,Tamion, Rodolphe. "Scalable Aerobic Oxidation of Alcohols Using Catalytic DDQ/HNO3". supporting information. p. 856 - 860. Retrieved 2020/07/14.
• 2、 Kim, Eunae,Kim, Hyun Jung,Cho, Seung-Sik,Shim, Jung-Hyun,Yoon, Goo. "Isolation, Semisynthesis, and Molecular Modeling of Deoxypodophyllotoxin Analogs for an Anti-oral Cancer Agent". . p. 472 - 475. Retrieved 2020/02/13.