4'-Demethylpodophyllotoxone
Basic information
- CAS
93780-84-8- Standard SMILES
COc1cc([C@@H]2c3cc4c(cc3C(=O)[C@H]3COC(=O)[C@H]23)OCO4)cc(OC)c1O- InChIKey
OJDRVIHXHQXFSH-RZAIGCCYSA-N- Molecular formula
- C21H18O8
- Average molar mass
- 398.4 g/mol
- Monoisotopic mass
- 398.10016753
Overview
8-(4-Hydroxy-3,5-dimethoxyphenyl)-5,12,14-trioxatetracyclo(7.7.0.0(3,7).0(11,15))hexadeca-1(16),9(10),11(15)-triene-2,6-dione has been reported in Podophyllum peltatum with data available.
Names & identifiers
- Preferred name
- 4'-Demethylpodophyllotoxone
- IUPAC
- (5aR,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-[2]benzofuro[5,6-f][1,3]benzodioxole-5,8-dione
- English name
- Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-5,8-dione, 5a,6,8a,9-tetrahydro-9-(4-hydroxy-3,5-dimethoxyphenyl)-, (5aR,8aR,9R)-
- Molecular formula
- C21H18O8
- Molecular weight
- 398.36
Names & synonyms
93780-84-84'-Demethylpodophyllotoxone(5ar,8ar,9r)-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione8-(4-Hydroxy-3,5-dimethoxyphenyl)-5,12,14-trioxatetracyclo(7.7.0.0(3,7).0(11,15))hexadeca-1(16),9(10),11(15)-triene-2,6-dioneFuro(3',4':6,7)naphtho(2,3-d)-1,3-dioxole-5,8-dione, 5a,6,8a,9-tetrahydro-9-(4-hydroxy-3,5-dimethoxyphenyl)-, (5aR-(5aalpha,8abeta,9alpha))-4-DeMethpodopyllotoxoneCHEMBL95683orb1941451DTXSID40917986HY-N12033DA-70085CS-0890724
Show more names
Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-5,8-dione, 5a,6,8a,9-tetrahydro-9-(4-hydroxy-3,5-dimethoxyphenyl)-, (5aR,8aR,9R)-
H50699T83320(5aR,8aR,9R)-9-(4-hydroxy-3,5-dimethoxy-phenyl)-5a,6,8a,9-tetrahydroisobenzofuro[6,5-f][1,3]benzodioxole-5,8-dione(5aR,8aR,9R)-9-(4-Hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione8-(4-Hydroxy-3,5-dimethoxyphenyl)-5,12,14-trioxatetracyclo[7.7.0.0<3,7>.0<11,15>]hexadeca-1(16),9(10),11(15)-triene-2,6-dione9-(4-Hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione
Properties
Computed structural properties
- XLogP
- 2.2
- Topological polar surface area
- 101 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 3
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 653
Physicochemical properties
- Boiling point
- 632.3 · 632.3±55.0 °C(Predicted)
- Density
- 1.441 · 1.441±0.06 g/cm3(Predicted)
- pka
- 9.87 · 9.87±0.40(Predicted)
- form
- Solid
- color
- White to off-white
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 280 · P280-P305+P351+P338
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P280-P305+P351+P338
Chemistry & industry
Applications
Uses4'-Demethylpodophyllotoxone is an intermediate product of the biotransformation of Alternaria alternata S-f6. After 4'-Demethylpodophyllotoxone is modified with 4-(2,3,5,6-tetramethylpyrazine-1) (4-TMP), the resulting novel compound can strongly inhibit the growth of human gastric cancer cell line (BGC-823)[1].
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Compound notes
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