4375-07-9

Basic information

• Product Name: (5R)-5β-(3,4,5-Trimethoxyphenyl)-7α-(hydroxymethyl)-8α-hydroxy-5,6,7,8-tetrahydronaphtho[2,3-d]-1,3-dioxole-6β-carboxylic acid 6,7-lactone
• Synonyms: (-)-Epipodophyllotoxin;(5R)-5,5aα,8aβ,9-Tetrahydro-9α-hydroxy-5β-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-6(8H)-one;(5R)-5,8,8aβ,9-Tetrahydro-9α-hydroxy-5β-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-(5aαH)-one;(5R)-5β-(3,4,5-Trimethoxyphenyl)-7α-(hydroxymethyl)-8α-hydroxy-5,6,7,8-tetrahydronaphtho[2,3-d]-1,3-dioxole-6β-carboxylic acid 6,7-lactone;(5R,5aR,8aR,9S)-5,8,8a,9-Tetrahydro-5-(3,4,5-trimethoxyphenyl)-9-hydroxyfuro[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one;Epipodophyllotoxin;(5S,5aR,8aR,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one;(5S,5aR,8aR,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[5,6-f][1,3]benzodioxol-8-one
• CAS NO: 4375-07-9
• Molecular Formula: C₂₂H₂₂O₈
• Molecular Weight: 414.40528
• Product Categories: Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 4375-07-9.mol
• Article Data: 44

Chemical Properties

• Melting Point: 160.3°C
• Boiling Point: 453.31°C (rough estimate)
• Appearance: /
• Density: 1.2649 (rough estimate)
• Refractive Index: 1.4480 (estimate)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 13.26±0.40(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: (5R)-5β-(3,4,5-Trimethoxyphenyl)-7α-(hydroxymethyl)-8α-hydroxy-5,6,7,8-tetrahydronaphtho[2,3-d]-1,3-dioxole-6β-carboxylic acid 6,7-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: (5R)-5β-(3,4,5-Trimethoxyphenyl)-7α-(hydroxymethyl)-8α-hydroxy-5,6,7,8-tetrahydronaphtho[2,3-d]-1,3-dioxole-6β-carboxylic acid 6,7-lactone(4375-07-9)
• EPA Substance Registry System: (5R)-5β-(3,4,5-Trimethoxyphenyl)-7α-(hydroxymethyl)-8α-hydroxy-5,6,7,8-tetrahydronaphtho[2,3-d]-1,3-dioxole-6β-carboxylic acid 6,7-lactone(4375-07-9)

Safety Data

• Hazardous Substances Data: 4375-07-9(Hazardous Substances Data)

Usage

Uses

Epipodophyllotoxins is a naturally occuring antitumors agent extracted from Mayapple plant.

Anticancer Research

It is a lignan compound; podophyllotoxin is isolated from the roots of Podophyllumpeltatum and P. emodi. Teniposide and etoposide are the semisynthetic derivativesof epipodophyllotoxin, and they are used for lymphomas and bronchial and testicularcancers (Shoeb 2006). These compounds break DNA molecules during the G2/Mphase in cell cycle by binding to tubulin and irreversibly inhibiting DNAtopoisomerase II (Balunas and Kinghorn 2005). Podophyllotoxin prevents thebreast cancer cell growth by modifying checkpoint kinase 2 (Chk2) signalingpathway and also induces apoptosis in non-small cell lung cancer by cell cyclearrest, autophagy, and ER stress (Singh et al. 2016b).

Upstream product

• 7401-22-1 9-Chloro-9-desoxypodophyllotoxin 
• 77287-70-8 5,6-dihydrocyclobuta[4,5]benzo[1,2-d][1,3]dioxol-5-ol 
• 13311-04-1 9r-(Tetrahydro-<2>pyranyloxy)-5c-(3,4,5-trimethoxyphenyl)-5,5a,8a,9-tetrahydro-8H-furo<3',4':6,7>naphtho<2,3-d>(1,3)-dioxol-6-on 
• 75-08-1 ethanethiol 
• 88775-47-7 (2E)-1-(2H-benzo[3,4-d]1,3-dioxolan-5-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 
• 106044-42-2 (5R,6R)-5-(3,4,5-Trimethoxy-phenyl)-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid 
• 477-67-8 (+/-)-isopodophyllinic acid 
• 99463-56-6 (2S,3S)-2-((4S,5R)-4-Benzo[1,3]dioxol-5-yl-2,2-di-tert-butyl-[1,3,2]dioxasilinan-5-yl)-3-hydroxy-3-(3,4,5-trimethoxy-phenyl)-propionic acid 
• 86301-75-9 dimethyl 4-(3,4-trans)-hydroxy-6,7-(methylenedioxy)-1-(1,2-cis)-(3',4',5'-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene-2,3-cis-dicarboxylate 
• 581069-50-3 4-tert-butyl-2-naphtho[2,3-d][1,3]dioxol-6-yl-4,5-dihydro-oxazole 
• 581069-48-9 4-isopropyl-2-naphtho[2,3-d][1,3]dioxol-6-yl-4,5-dihydro-oxazole 
• 581069-45-6 6.7-Methylendioxy-1-<3.4.5-trimethoxy-phenyl>-1.2-dihydro-naphthoesaeure-(2)-methylester 
• 1185862-69-4 7-chlorodeoxypodophyllotoxin 
• 67-64-1 acetone 

Downstream Products

• 59123-24-9 (±)-β-apopicropodophyllin 
• 477-51-0 deoxypicropodophyllotoxin 
• 6559-91-7 (+/-)-4'-O-demethyl-1-epipodophyllotoxin 
• 136723-80-3 4-deoxy-4-allyl-(epi)-podophyllotoxin 
• 1174-96-5 6,7-O-Demethylen-epipodophyllotoxin 
• 138456-91-4 6,7-O,O-demethylene-4'-O-demethylepipodophyllotoxin 
• 477-48-5 podophyllotoxone 
• 78339-52-3 epipodophyllol 
• 4375-06-8 epipicropodophyllotoxin 
• 518-28-5 podofilox 
• 136755-67-4 1-β-propyl-1-desoxypodophyllotoxin 
• 155252-34-9 4β-azido-4-deoxypodophyllotoxin 
• 1244966-32-2 C₃₁H₂₇NO₁₃ 
• 1244966-31-1 C₃₁H₂₈O₁₁ 

Relevant articles and documents

Total synthesis of podophyllotoxin and select analog designs via C–H activation

An account of our previously disclosed total synthesis of the aryltetralin lignan natural product podophyllotoxin, a building block used in the synthesis of the FDA-approved anticancer drug etoposide, is disclosed. A C–H activation disconnection was viewed as being amenable to the preparation of E-ring modified analogs but proved challenging to execute. Various insights into palladium-catalyzed C–H arylation reactions on complex scaffolds are reported ultimately leading to the implementation of this strategy and the synthesis of compounds inaccessible by semisynthetic means.

Chemoenzymatic Total Synthesis of Deoxy-, epi-, and Podophyllotoxin and a Biocatalytic Kinetic Resolution of Dibenzylbutyrolactones

Podophyllotoxin is probably the most prominent representative of lignan natural products. Deoxy-, epi-, and podophyllotoxin, which are all precursors to frequently used chemotherapeutic agents, were prepared by a stereodivergent biotransformation and a biocatalytic kinetic resolution of the corresponding dibenzylbutyrolactones with the same 2-oxoglutarate-dependent dioxygenase. The reaction can be conducted on 2 g scale, and the enzyme allows tailoring of the initial, “natural” structure and thus transforms various non-natural derivatives. Depending on the substitution pattern, the enzyme performs an oxidative C?C bond formation by C?H activation or hydroxylation at the benzylic position prone to ring closure.

Divergent Asymmetric Syntheses of Podophyllotoxin and Related Family Members via Stereoselective Reductive Ni-Catalysis

A nickel-catalyzed reductive cascade approach to the efficient construction of diastereodivergent cores embedded in podophyllum lignans is developed for the first time. Their gram-scale access paved the way for unified syntheses of naturally occurring podophyllotoxin and other members.