4354-76-1

Basic information

• Product Name: PODOPHYLLOTOXIN
• Synonyms: PODOPHYLLIC ACID LACTONE;(5R,5AR,8AR,9R)-9-HYDROXY-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;PODOPHYLLOTOXIN(P);5,8,8a,9-Tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one;(5R,5AR,8aR,9R)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,;Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5alphaH)-one,5,8,8alpha,9-tetrahydro-9-hydroxy-5-(3,4,5-triMethoxyphenyl)-;(5R,5aR,8aR,9R)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
• CAS NO: 4354-76-1
• Molecular Formula: C22H22O8
• Molecular Weight: 414.41
• EINECS: 208-250-4
• Product Categories: Anti-viral Compounds;Anti-virals;Inhibitors;Intermediates & Fine Chemicals;Non-nucleoside Reverse Transcriptase;Pharmaceuticals
• Mol File: 4354-76-1.mol
• Article Data: 14

Chemical Properties

• Melting Point: 183-184 °C(lit.)
• Boiling Point: 597.9 °C at 760 mmHg
• Flash Point: 210.2 °C
• Appearance: White crystalline powder
• Density: 1.370
• Vapor Pressure: 3.82E-15mmHg at 25°C
• Refractive Index: 1.605
• Storage Temp.: 2-8°C
• PKA: 13.26±0.40(Predicted)
• CAS DataBase Reference: PODOPHYLLOTOXIN(CAS DataBase Reference)
• NIST Chemistry Reference: PODOPHYLLOTOXIN(4354-76-1)
• EPA Substance Registry System: PODOPHYLLOTOXIN(4354-76-1)

Safety Data

• Hazard Codes: T
• Statements: 21-25-36/37/38
• Safety Statements: 36/37/39-45
• RIDADR: UN 3462 6.1/PG 2
• WGK Germany: 3
• RTECS: LV2500000
• F: 1-8-10
• Hazardous Substances Data: 4354-76-1(Hazardous Substances Data)

Usage

Chemical Description

Podophyllotoxin and 4-demethoxypodophylltoxin are compounds that have been studied for their potential as anticancer agents.

InChI:InChI=1/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19+,20-/m0/s1

Upstream product

• 518-28-5 podofilox 
• 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 
• 104715-48-2 (5S,6S,7S,8R)-7-Aminomethyl-8-hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid 
• 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 
• 100146-47-2 (5R,6R)-8-Hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid 
• 106044-49-9 (5S,6S,7S,8R)-7-Cyano-8-hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid 
• 106044-47-7 (3aR,4S,5S,10bR)-3-Chloro-5-(3,4,5-trimethoxy-phenyl)-3a,4,5,10b-tetrahydro-1,7,9-trioxa-2-aza-dicyclopenta[a,g]naphthalene-4-carboxylic acid 
• 106044-46-6 (3aS,4R,5R,10bS)-3-Bromo-5-(3,4,5-trimethoxy-phenyl)-3a,4,5,10b-tetrahydro-1,7,9-trioxa-2-aza-dicyclopenta[a,g]naphthalene-4-carboxylic acid benzhydryl ester 
• 75403-99-5 (2S,3S)-2-(Benzo[1,3]dioxole-5-carbonyl)-3-(3,4,5-trimethoxy-phenyl)-cyclopropanecarboxylic acid ethyl ester 
• 106044-41-1 (5S,6S)-5-(3,4,5-Trimethoxy-phenyl)-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid benzhydryl ester 
• 106044-41-1 (5S,6R)-5-(3,4,5-Trimethoxy-phenyl)-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid benzhydryl ester 
• 75404-00-1 ethyl rel-(3R,4R)-6,7-methylenedioxy-1-oxo-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene-3-carboxylate 

Downstream Products

• 59123-24-9 (±)-β-apopicropodophyllin 
• 477-51-0 deoxypicropodophyllotoxin 
• 6559-91-7 (+/-)-4'-O-demethyl-1-epipodophyllotoxin 
• 33419-42-0 etoposide 
• 112146-42-6 4′-demethyl-(epi)-podophyllotoxin 4-O-2″-deoxy-2″-amino-4″,6″-di-O-ethylidene-β-D-glucopyranoside 
• 131118-85-9 {(2R,4aR,6R,7R,8R,8aS)-8-Hydroxy-6-[(5S,5aR,8aR,9R)-9-(4-hydroxy-3,5-dimethoxy-phenyl)-8-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yloxy]-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-carbamic acid benzyl ester 
• 131118-85-9 {(2S,4aS,6S,7S,8S,8aR)-8-Hydroxy-6-[(5S,5aR,8aR,9R)-9-(4-hydroxy-3,5-dimethoxy-phenyl)-8-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yloxy]-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-carbamic acid benzyl ester 
• 131118-85-9 {(2R,4aR,6R,7R,8R,8aS)-8-Hydroxy-6-[(5R,5aS,8aS,9S)-9-(4-hydroxy-3,5-dimethoxy-phenyl)-8-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yloxy]-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-carbamic acid benzyl ester 
• 131118-85-9 {(2S,4aS,6S,7S,8S,8aR)-8-Hydroxy-6-[(5R,5aS,8aS,9S)-9-(4-hydroxy-3,5-dimethoxy-phenyl)-8-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yloxy]-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-carbamic acid benzyl ester 
• 92206-80-9 1-O-(2,3-di-O-chloroacetyl-4:6-O-ethylidene-β-D-glucopyranosyl)-<(-)-4'-O-chloroacetyl-1-epipodophyllotoxin> 
• 92206-80-9 Chloro-acetic acid 4-{(5R,5aR,8aR,9S)-9-[(2S,4aS,6S,7S,8R,8aS)-7,8-bis-(2-chloro-acetoxy)-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl}-2,6-dimethoxy-phenyl ester 
• 92206-80-9 1-O-(2,3-di-O-chloroacetyl-4:6-O-ethylidene-β-D-glucopyranosyl)-<(+)-4'-O-chloroacetyl-1-epipodophyllotoxin> 
• 92206-80-9 Chloro-acetic acid 4-{(5S,5aS,8aS,9R)-9-[(2S,4aS,6S,7S,8R,8aS)-7,8-bis-(2-chloro-acetoxy)-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl}-2,6-dimethoxy-phenyl ester 
• 112146-51-7 1-O-(2-benzyloxycarbonylamido-3-chloroacetyl-2-deoxy-4:6-O-ethylidene-β-D-glucopyranosyl)-<(-)-4'-O-chloroacetyl-1-epipodophyllotoxin> 

Relevant articles and documents

Silenes in organic synthesis: A concise synthesis of (±)-epi- picropodophyllin

A concise, seven step synthesis of the aryl tetralin lignan lactone epi-picropodophyllin from piperonal is described. The key steps are a silene diene Diels-Alder reaction and the Hosomi-Sakurai reaction of the resultant silacyclohexene. The Royal Society

Efficient synthesis of 1-aryl-3,4-dihydro-4-hydroxynaphthalene: Application to the stereocontrolled synthesis of (±)-isopicropodophyllin and (±)-isopodophyllotoxin

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Synthesis of Podophyllum Lignans via an Isolable o-Quinonoid Pyrone

The 2-benzopyran-3-one 10 is a stable, isolable and useful Diels-Alder diene; its methyl 4-benzoyloxycrotonate adduct 23 formed regioselectively and stereoselectively in acetonitrile is reduced with H2/Pd to give 31 with inversion of C-1 stereochemistry.T