477-49-6

Basic information

• Product Name: Podophyllotoxone
• Synonyms: Podophyllotoxone;(5aR)-5aα,6,8aβ,9-Tetrahydro-9α-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-5,8-dione;(5R)-5,5aα,8,8aβ-Tetrahydro-5β-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-6,9-dione;(5R)-5,8,8aβ,9-Tetrahydro-5β-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-6(5aαH),9-dione;(5R)-5aα,8aβ-Dihydro-5β-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-6,9(5H,8H)-dione;(5R)-5β-(3,4,5-Trimethoxyphenyl)-5,8,8aβ,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-6,9(5aαH)-dione;Podophyllotoxinone;(-)-podophyllotoxon
• CAS NO: 477-49-6
• Molecular Formula: C₂₂H₂₀O₈
• Molecular Weight: 362.332
• Mol File: 477-49-6.mol
• Article Data: 35

Chemical Properties

• Melting Point: 191.73℃
• Boiling Point: 602.3±55.0 °C(Predicted)
• Appearance: /
• Density: 1.365±0.06 g/cm3 (20 ºC 760 Torr)
• CAS DataBase Reference: Podophyllotoxone(CAS DataBase Reference)
• NIST Chemistry Reference: Podophyllotoxone(477-49-6)
• EPA Substance Registry System: Podophyllotoxone(477-49-6)

Safety Data

• Hazardous Substances Data: 477-49-6(Hazardous Substances Data)

Usage

Description

Podophyllotoxone is a naturally occurring flavonoid compound derived from the Podophyllum plant species, which has demonstrated significant cell apoptosis and antiproliferative effects against various human cancer cell lines. It is known for its potential in the development of chemotherapeutic agents due to its ability to inhibit cell division and induce cell death in cancer cells.

Uses

Used in Pharmaceutical Industry:
Podophyllotoxone is used as a chemotherapeutic agent for its significant cell apoptosis and antiproliferative effects against human PC-3 (prostate cancer) and Bcap-37 (breast cancer) cancer cell lines. It is particularly effective in targeting and treating these types of cancers, as it can inhibit the uncontrolled cell division and growth associated with cancerous cells.
Additionally, Podophyllotoxone has been found to have potential applications in other cancer types and is currently under investigation for its use in combination therapies to enhance the effectiveness of existing treatments and overcome drug resistance in cancer cells.

Upstream product

• 518-28-5 podofilox 
• 1180-34-3 podophyllotoxinyl acetate 
• 4375-07-9 epipodophyllotoxin 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 56579-86-3 2-(3,4-methylenedioxyphenyl)-1,3-dithiane 
• 90359-54-9 3,4-methylenedioxycinnamyl 3-(3,4,5-trimethoxyphenyl)acrylate 
• 620116-56-5 (5S,5aS,8aR,9R)-5-(Dimethyl-phenyl-silanyl)-8-oxo-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 
• 620116-55-4 (5S,6S)-5-(Dimethyl-phenyl-silanyl)-6-(3,4,5-trimethoxy-phenoxythiocarbonyloxymethyl)-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid allyl ester 
• 620116-47-4 9-(tert-butyl-dimethyl-silanyloxy)-5-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one 
• 620116-46-3 thiocarbonic acid O-[5-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydro-naphtho[2,3-d][1,3]dioxol-6-ylmethyl] ester O-(3,4,5-trimethoxy-phenyl) ester 
• 620116-51-0 (5S,6S)-5-(Dimethyl-phenyl-silanyl)-6-((S)-4-isopropyl-4,5-dihydro-oxazol-2-yl)-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid allyl ester 
• 620622-68-6 podophyllotoxin 
• 620116-54-3 (5S,6S)-5-(Dimethyl-phenyl-silanyl)-6-hydroxymethyl-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid allyl ester 
• 620116-53-2 (5S,6S)-5-(Dimethyl-phenyl-silanyl)-6-formyl-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid allyl ester 

Downstream Products

• 42123-27-3 dehydropodophyllotoxin 
• 55515-07-6 (1α,2α,3α)-podophyllotoxin 
• 157904-78-4 <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 
• 477-48-5 (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 
• 4375-07-9 epipodophyllotoxin 
• 518-28-5 podofilox 
• 177990-69-1 isoxazolopodophyllic acid 
• 918108-96-0 thuriferic acid methyl ester 
• 138935-77-0 4-Hydroxy-3-methyl-6,7-(methylenedioxy)-1-(3,4,5-trimethoxyphenyl)-2-naphthoic acid 
• 303158-21-6 (6S,7R,8R)-6,7-Bis-hydroxymethyl-8-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxol-5-ol 
• 211043-48-0 (5R,6R,7R)-7-Hydroxymethyl-8-oxo-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid butyl ester 
• 124131-03-9 (5R,6R,7R)-7-Hydroxymethyl-8-oxo-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid ethyl ester 
• 211043-47-9 (5R,6R,7R)-7-Hydroxymethyl-8-oxo-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid propyl ester 
• 211043-39-9 (5R,6R,7R)-methyl 7-(hydroxymethyl)-8-oxo-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydronaphtho[2,3-d][1,3]dioxole-6-carboxylate 

Relevant articles and documents

Synthesis and In Vitro Anticancer Activity of Triazolyl Analogs of Podophyllotoxin, a Naturally Occurring Lignin

Abstract: A series of triazolyl-modified podophyllotoxin analogs have been designed and synthesized by utilizing Huisgen 1,3-dipolar cycloaddition in order to develop potent antitumor agents. The synthesized analogs were assessed for in vitro anticancer a

Base-free oxidation of alcohols enabled by nickel(ii)-catalyzed transfer dehydrogenation

An efficient nickel(ii)-catalyzed transfer dehydrogenation oxidation of alcohols is reported that relies on cyclohexanone as the formal oxidant and does not require the use of an external base. The synthetic utility of this protocol is demonstratedviathe facile oxidation of structurally complicated natural products.

Asymmetric Chemoenzymatic Synthesis of (?)-Podophyllotoxin and Related Aryltetralin Lignans

(?)-Podophyllotoxin is one of the most potent microtubule depolymerizing agents and has served as an important lead compound in antineoplastic drug discovery. Reported here is a short chemoenzymatic total synthesis of (?)-podophyllotoxin and related aryltetralin lignans. Vital to this approach is the use of an enzymatic oxidative C?C coupling reaction to construct the tetracyclic core of the natural product in a diastereoselective fashion. This strategy allows gram-scale access to (?)-deoxypodophyllotoxin and is readily adaptable to the preparation of related aryltetralin lignans.