4'-Demethylpodophyllotoxin

Base Information

• Chemical Name: 4'-Demethylpodophyllotoxin
• CAS No.: 40505-27-9
• Molecular Formula: C21H20O8
• Molecular Weight: 400.385
• UNII: 7N5E50463V
• DSSTox Substance ID: DTXSID201311785
• Nikkaji Number: J53.987B
• Wikidata: Q27105499
• ChEMBL ID: CHEMBL28941
• Mol file: 40505-27-9.mol

Synonyms:4'-Demethylpodophyllotoxin;40505-27-9;(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;4-Demethylpodophyllotoxin;BRN 0099005;4'-O-demethylpodophyllotoxin;CHEBI:1730;(5R,5aR,8aR,9R)-5-hydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one;UNII-7N5E50463V;MFCD01725607;7N5E50463V;Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5ah)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-, (5R-(5-alpha,5a-beta,8a-alpha,9-alpha))-;(5R,5aR,8aR,9R)-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-Demethyl-Podophyllotoxin;5-19-10-00665 (Beilstein Handbook Reference);4\'-demethylpodophyllotoxin;4'-Demethyl-Podophyllotoxin;CHEMBL28941;O(4')-demethylpodophyllotoxin;SCHEMBL12278154;DTXSID201311785;HY-N2323;s3908;AKOS015895546;CCG-268651;FD10224;AC-34637;AS-58706;LS-70854;CS-0020771;J-515253;Q27105499;(5R,5aR,8aR,9R)-5-hydroxy-9-(4-hydroxy-3,5-dimethoxy-phenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[6,5-f][1,3]benzodioxol-8-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;5,8,8a,9,-Tetrahydro-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one;FURO(3',4':6,7)NAPHTHO(2,3-D)-1,3-DIOXOL-6(5AH)-ONE, 5,8,8A,9-TETRAHYDRO-9-HYDROXY-5-(4-HYDROXY-3,5-DIMETHOXYPHENYL)-, (5R,5AR,8AR,9R)-;Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-, [5R-(5.alpha.,5a.beta.,8a.alpha.,9.alpha.)]-

Chemical Property of 4'-Demethylpodophyllotoxin

Chemical Property:

• Melting Point: 250-252 °C
• Boiling Point: 626.5 °C at 760 mmHg
• PKA: 9.94±0.40(Predicted)
• Flash Point: 224.4 °C
• PSA: 103.68000
• Density: 1.446 g/cm³
• LogP: 2.10620
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 400.11581759
• Heavy Atom Count: 29
• Complexity: 614

Purity/Quality:

≥98% ^*data from raw suppliers

4’-Demethylpodophyllotoxin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1O)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)O
• Isomeric SMILES: COC1=CC(=CC(=C1O)OC)[C@H]2[C@@H]3[C@H](COC3=O)[C@H](C4=CC5=C(C=C24)OCO5)O

Technology Process of 4'-Demethylpodophyllotoxin

There total 6 articles about 4'-Demethylpodophyllotoxin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 5.0%

→ 4-demethylpodophyllotoxin (40505-27-9)

Guidance literature:

Reference yield:

(+/-)-podophyllotoxin (477-47-4,518-28-5,4354-76-1,4375-06-8,4375-07-9,26540-82-9,55568-79-1,55568-80-4,60660-50-6,62319-21-5,77519-37-0,77519-38-1,79355-67-2,86334-73-8,118627-04-6,122871-77-6,122871-79-8,122871-81-2) → (+/-)-4'-O-demethyl-1-epipodophyllotoxin (6559-91-7,40505-27-9,77519-36-9,87584-72-3,96554-39-1,104264-48-4,107079-65-2,112066-16-7,112246-55-6)

Guidance literature:

With hydrogen bromide; barium carbonate; Yield given. Multistep reaction; 1.) Et₂O, ethylene dichloride, 2.) acetone, H₂O;

DOI:10.1246/cl.1987.799

Reference yield:

C28H23NO11 → 4-demethylpodophyllotoxin (40505-27-9)

Guidance literature:

With methanol; potassium carbonate; for 3h; Inert atmosphere;

upstream raw materials:

podofilox

4'-demethylepipodophyllotoxin

(+/-)-podophyllotoxin

Downstream raw materials:

4β-amino-4'-dimethyl-4-deoxy-epipodophyllotoxin

Refernces

• 1、 -. "ORGANOPLATINUM COMPOUNDS AND PHARMACEUTICAL COMPOSITION THEREOF AND METHOD OF PREPARING CRYSTAL OF hTop2". Paragraph 0034; 0036. . Retrieved 2020/10/21.
• 2、 -. "Etoposide analogues". . . Retrieved 2008/06/13.