40505-27-9

Basic information

• Product Name: 4'-Demethylpodophyllotoxin
• Synonyms: 9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5ah)-one;4'-demethylpodophyllotoxin;(5R)-5,8,8aβ,9-Tetrahydro-5β-(3,5-dimethoxy-4-hydroxyphenyl)-9β-hydroxyfuro[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-6(5aαH)-one;(5R)-5,8,8aβ,9-Tetrahydro-9β-hydroxy-5β-(3,5-dimethoxy-4-hydroxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aαH)-one;(5R)-5β-(4-Hydroxy-3,5-dimethoxyphenyl)-9β-hydroxy-5,5aα,6,8,8aβ,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-6-one;(5R)-9β-Hydroxy-5,8,8aβ,9-tetrahydro-5β-(4-hydroxy-3,5-dimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-6(5aαH)-one;(5R,5AR,8aR,9R)-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one
• CAS NO: 40505-27-9
• Molecular Formula: C₂₁H₂₀O₈
• Molecular Weight: 400.3787
• Mol File: 40505-27-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 250-252 °C
• Boiling Point: 626.5 °C at 760 mmHg
• Flash Point: 224.4 °C
• Appearance: /
• Density: 1.446 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 9.94±0.40(Predicted)
• CAS DataBase Reference: 4'-Demethylpodophyllotoxin(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-Demethylpodophyllotoxin(40505-27-9)
• EPA Substance Registry System: 4'-Demethylpodophyllotoxin(40505-27-9)

Safety Data

• Hazardous Substances Data: 40505-27-9(Hazardous Substances Data)

Usage

Definition

ChEBI: An organic heterotetracyclic compound that is podophyllotoxin in which the methyl ether group at position 4 of the trimethoxyphenyl group has been cleaved to afford the corresponding phenol.

Upstream product

• 518-28-5 podofilox 
• 477-47-4 (+/-)-podophyllotoxin 
• 6559-91-7 4'-demethylepipodophyllotoxin 

Downstream Products

• 1388218-51-6 C₂₂H₁₉NO₇S 
• 1388218-52-7 C₂₄H₂₅N₃O₈S 
• 1388218-50-5 C₂₄H₂₃N₃O₈ 
• 1278585-93-5 4β-(3-benzoylthioureido)-4'-O-demethyl-4-desoxypodophyllotoxin 
• 1278585-97-9 4β-[3-(4-chlorobenzoyl)thioureido]-4'-O-demethyl-4-desoxypodophyllotoxin 
• 1429193-53-2 C₂₇H₂₄N₂O₉S 
• 1429193-54-3 C₂₇H₂₄N₂O₈S₂ 
• 1429193-55-4 C₃₃H₂₈N₂O₈S 
• 118139-42-7 4β-amino-4'-dimethyl-4-deoxy-epipodophyllotoxin 
• 746639-24-7 4β-iodo-4-O-demethylpodophyllotoxin 
• 681138-12-5 4β-(4-(ethylacetic-2-yl)thiazol-2-yl)amino-4′-O-demethyl-4-deoxypodophyllotoxin 

Relevant articles and documents

HUMAN TOPOISOMERASE II-TARGETING ORGANOPLATINUM COMPOUNDS

Some organoplatinum compounds have been synthesized. These organoplatinum compounds are designed to be human Topoisomerase II-targeting drugs.

Comparative study of microtubule inhibitors - Estramustine and natural podophyllotoxin conjugated PAMAM dendrimer on glioma cell proliferation

The synthetic estramustine (EM) and natural podophyllotoxin (PODO) anti-mitotic agents that inhibit tubulin polymerization are known anticancer agents. As low bioavailability limits their anticancer properties, we investigated whether conjugation with PAMAM dendrimer (D) could enhance the activity of D-EM and D-PODO by altering their release pattern. Release kinetics indicated synthesized conjugates to be stable against hydrolytic cleavage and showed sustained release characteristics. However, release of D-EM was slow compared to D-PODO conjugate. Antitumor effect of these conjugates on glioma cells revealed (i) increased cell death and cell cycle arrest (ii) decreased migration and (iii) increased tubulin depolymerization as compared to free drug. Importantly, the effects of natural PODO conjugate on glioma cell survival and migration is more pronounced than D-EM.

Syntheses of All Four Possible Diastereomers of Etoposide and Its Aminoglycosidic Analogues via Optical Resolution of (+/-)-Podophyllotoxin by Glycosidation with D- and L-Sugars

Syntheses of all four possible diastereomers of etoposide and its aminoglycosidic analogues have been achieved via optical resolution of (+/-)-podophyllotoxin by glycosidation with D- and L-sugars.