138456-91-4

Basic information

• Product Name: (3aR,4S,9R,9aR)-4,6,7-trihydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-3a,4,9,9a-tetrahydronaphtho[2,3-c]furan-1(3H)-one
• Synonyms: (3aR,4S,9R,9aR)-4,6,7-Trihydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-3a,4,9,9a-tetrahydronaphtho(2,3-c)furan-1(3H)-one; naphtho[2,3-c]furan-1(3H)-one, 3a,4,9,9a-tetrahydro-4,6,7-trihydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-, (3aR,4S,9R,9aR)-
• CAS NO: 138456-91-4
• Molecular Formula: C₂₀H₂₀O₈
• Molecular Weight: 388.368
• Mol File: 138456-91-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 687.9°C at 760 mmHg
• Flash Point: 248.5°C
• Density: 1.479g/cm³
• Vapor Pressure: 7.24E-20mmHg at 25°C
• Refractive Index: 1.661
• CAS DataBase Reference: (3aR,4S,9R,9aR)-4,6,7-trihydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-3a,4,9,9a-tetrahydronaphtho[2,3-c]furan-1(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR,4S,9R,9aR)-4,6,7-trihydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-3a,4,9,9a-tetrahydronaphtho[2,3-c]furan-1(3H)-one(138456-91-4)
• EPA Substance Registry System: (3aR,4S,9R,9aR)-4,6,7-trihydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-3a,4,9,9a-tetrahydronaphtho[2,3-c]furan-1(3H)-one(138456-91-4)

Safety Data

• Hazardous Substances Data: 138456-91-4(Hazardous Substances Data)

Upstream product

• 518-28-5 podofilox 
• 6559-91-7 4'-demethylepipodophyllotoxin 
• 4375-07-9 epipodophyllotoxin 

Downstream Products

• 1356151-85-3 C₂₂H₂₄O₈ 
• 138355-91-6 6,7-O,O-demethylene-6,7-O,O-dimethyl-4β-[4-(ethoxycarbonyl)anilino]-4-desoxypodophyllotoxin 
• 138355-95-0 6,7-O,O-demethylene-6,7-O,O-dimethyl-4'-O-demethyl-4β-[4-(ethoxycarbonyl)anilino]-4-desoxypodophyllotoxin 
• 138355-90-5 6,7-O,O-demethylene-6,7-O,O-dimethyl-4β-(4-nitroanilino)-4-desoxypodophyllotoxin 
• 138355-94-9 6,7-O,O-demethylene-6,7-O,O-dimethyl-4'-O-demethyl-4β-(4-nitroanilino)-4-desoxypodophyllotoxin 
• 138355-92-7 6,7-O,O-demethylene-6,7-O,O-dimethyl-4β-(4-cyanoanilino)-4-desoxypodophyllotoxin 
• 138355-96-1 6,7-O,O-demethylene-6,7-O,O-dimethyl-4'-O-demethyl-4β-(4-cyanoanilino)-4-desoxypodophyllotoxin 
• 138355-93-8 6,7-O,O-demethylene-6,7-O,O-dimethyl-4β-(4-fluoroanilino)-4-desoxypodophyllotoxin 
• 138355-97-2 6,7-O,O-demethylene-6,7-O,O-dimethyl-4'-O-demethyl-4β-(4-fluoroanilino)-4-desoxypodophyllotoxin 

Relevant articles and documents

Synthesis and evaluation of novel podophyllotoxin analogs

Because prior studies have shown inconsistency between structure-activity relationships for podophyllotoxin derivatives as topoisomerase II inhibitors and cytotoxic agents, eight novel podophyllotoxin analogs were synthesized to further explore the effects of structural variations on both A and D rings on activity. The new compounds contain a 4,5-dimethoxy substituted A ring and opened D-ring variants and were prepared by appropriate functional and stereochemical operations at the methylenedioxy group, C7, C8, and C8′. Four compounds (15, 18, 21 and 22) demonstrated noticeable inhibitory activity against A549, DU145, KB and KBvin tumor cells, and the most active compound 18 showed IC50 values less than 10 μg/mL.

Antitumor agents. I. DNA topoisomerase II inhibitory activity and the structural relationship of podophyllotoxin derivatives as antitumor agents

Various podophyllotoxin derivatives from desoxypodophyllotoxin (DPT) were synthesized to examine the structural relationships between the biological significance (cytotoxic effect, effects on DNA topoisomerase II and tubulin polymerization) in vitro and a