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Podophyllotoxin

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Identification
Molecular formula
C22H22O8
CAS number
518-28-5
IUPAC name
(5R,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
State
State
Podophyllotoxin is typically a solid at room temperature, presenting as a crystalline powder or crystals.
Melting point (Celsius)
183.00
Melting point (Kelvin)
456.15
Boiling point (Celsius)
510.00
Boiling point (Kelvin)
783.15
General information
Molecular weight
414.40g/mol
Molar mass
414.4010g/mol
Density
1.3500g/cm3
Appearence
Podophyllotoxin appears as a white or off-white crystalline powder.
Comment on solubility

Solubility of (5R,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

This compound, with its complex molecular structure, exhibits unique solubility characteristics influenced by its functional groups and overall architecture. Here are some key points to consider regarding its solubility:

  • Solvent Polarity: The presence of multiple methoxy groups indicates that the compound may have a tendency to dissolve better in polar organic solvents like ethanol, methanol, or acetone.
  • Hydrogen Bonding: The hydroxyl (-OH) group can engage in hydrogen bonding, potentially increasing solubility in water compared to similar compounds lacking this functional group.
  • Temperature Influence: As with many organic compounds, solubility may improve at elevated temperatures, enhancing molecular mobility and interaction with solvent molecules.
  • pH Sensitivity: Depending on the pH of the solution, the solubility might change notably due to protonation or deprotonation of the hydroxyl group, which can either enhance or hinder the solubility in aqueous environments.

In summary, while the specific solubility values may vary, the interactions between the compound's functional groups and the solvent are critical determinants. Ultimately, it can be concluded that this compound is likely to exhibit moderate solubility in polar solvents, particularly benefiting from conditions that promote enhanced molecular interactions.

Interesting facts

Interesting Facts about (5R,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

This fascinating compound is an intriguing member of the extensive family of organic compounds known as benzodioxoles. Its complex structure presents unique characteristics that are of great interest to chemists and researchers alike.

Key Features

  • Structural Complexity: The compound features multiple rings and functional groups, presenting opportunities for diverse chemical reactions and bindings.
  • Bioactivity Potential: Compounds in this class are often investigated for their potential biological activity, including antioxidant and anti-inflammatory properties.
  • Natural Occurrence: Many similar compounds are derived from natural sources, particularly plants, highlighting their importance in herbal medicine.
  • Research Interest: Ongoing research explores the implications of such compounds in drug development, potentially leading to advancements in treatments for various health conditions.

One of the fascinating aspects of this compound is its range of substituents, such as the 3,4,5-trimethoxyphenyl group. This specific configuration adds to its potential pharmacological activity, making it a candidate for further study in medicinal chemistry.

As a scientist or student of chemistry, one might appreciate the challenge of synthesizing such complex molecules and understanding their intricate mechanisms of action. The exploration of this compound and similar structures could ultimately pave the way for innovative therapeutic solutions.

In summary, (5R,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 presents a rich avenue for scientific exploration, combining the beauty of structural elegance with promising biological potential.

Synonyms
podophyllotoxin
Podofilox
518-28-5
(-)-Podophyllotoxin
Podophyllotoxin 7
Podophyllinic acid lactone
Warticon
Podofilm
Podophilox
CCRIS 565
HSDB 7238
EINECS 208-250-4
NSC 24818
NSC-24818
DTXSID3045645
UNII-L36H50F353
CHEBI:50305
AI3-50456
L36H50F353
(5R,5aR,8aR,9R)-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)-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
Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, (5R-(5alpha,5abeta,8aalpha,9alpha))-
DTXCID1025645
(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
PODOPHYLLOTOXIN (MART.)
PODOPHYLLOTOXIN [MART.]
PODOPHYLLOTOXIN (EP MONOGRAPH)
PODOPHYLLOTOXIN [EP MONOGRAPH]
(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
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
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
(5R,5aR,8aR,9R)-5,8,8a,9-tetrahydro-9-hdroxy-5-(3,4,5-trimethoxyphenyl)furo-
1-hydroxy-2-hydroxymethyl-6,7-methylenedioxy-4-(3',4',5'-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthal ene-3-carboxylic acid lactone
208-250-4
Condylox
Condyline
Wartec
Podofilox [USAN]
MFCD00075290
(5R,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
NSC24818
CHEMBL61
(10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-one
MLS000069495
Podofilox (USAN)
NCGC00022001-05
Podophyllum
SMR000059121
(5R,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
(5R,5aR,8aR,9R)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one
Podocon-25
SR-05000001749
MLS002702981
Podofillina
Podophylotoxin
Mayapple isolate
Condylox (TN)
CAS-518-28-5
Prestwick_1018
Podofilox (Standard)
Podofillina [Italian]
Podophyllotoxin (BAN)
Spectrum_000199
PODOFILOX [HSDB]
Opera_ID_1397
Prestwick0_000782
Prestwick1_000782
Prestwick2_000782
Prestwick3_000782
Spectrum2_000878
Spectrum4_000592
Spectrum5_001368
PODOFILOX [VANDF]
UPCMLD-DP035
PODOPHYLLOTOXIN [MI]
SCHEMBL42243
BSPBio_000884
BSPBio_002352
KBioGR_001084
KBioSS_000679
MLS001148204
MLS002172467
MLS006010754
MLS006011412
BIDD:GT0123
DivK1c_000292
UNII-16902YVY2B
SPBio_000955
SPBio_002823
BPBio1_000974
CCRIS 4391
PODOFILOX [ORANGE BOOK]
PODOPHYLLOTOXIN [WHO-DD]
UPCMLD-DP035:001
UPCMLD-DP035:002
BCBcMAP01_000165
GTPL13598
HMS500O14
KBio1_000292
KBio2_000679
KBio2_003247
KBio2_005815
NINDS_000292
16902YVY2B
GLXC-10126
HMS1570M06
HMS2093P16
HMS2097M06
HMS2235A23
HMS3259J19
HMS3714M06
Pharmakon1600-02300332
ALBB-020906
BCP24085
FURO(3',4':6,7)NAPHTHO(2,3-D)-1,3-DIOXOL-6(5AH)-ONE, 5,8,8A,9-TETRAHYDRO-9-HYDROXY-5-(3,4,5-TRIMETHOXYPHENYL)-, (5R-(5.ALPHA.,5A.BETA.,8A.ALPHA.,9.ALPHA.))-
Podophyllotoxin, analytical standard
EINECS 232-546-2
Tox21_110874
Tox21_202922
B18-5C
BBL033695
BDBM50035218
CCG-39894
HY-15552R
MSK000573
NSC759591
STK801918
AKOS000265559
Tox21_110874_1
AC-1656
CS-1185
DB01179
FP05386
KS-1281
NC00675
ND-1185
NSC-759591
SDCCGMLS-0066888.P001
IDI1_000292
SMP1_000243
NCGC00022001-03
NCGC00022001-07
NCGC00022001-08
NCGC00022001-09
NCGC00022001-10
NCGC00022001-11
NCGC00022001-13
NCGC00022001-14
NCGC00260468-01
(5R,9R,5aR,8aR)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,9,5a,8a-pentahydro-2H -isobenzofurano[5',6'-2,1]benzo[4,5-d]1,3-dioxolan-6-one
1,3,3a,4,9,9a-Hexahydro-9-hydroxy-6,7-(methylenedioxy)-4-(3',4',5'-trimethoxyphenyl)benz(f)isobenzofuran-3-one
furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, (5R,5aR,8aR,9R)-
HY-15552
NCI60_001981
RD4-6269
1ST000573
NS00094687
P1771
EN300-52746
D05529
A828801
AO-228/21245006
Q421193
SR-01000003030
SR-01000003030-3
SR-05000001749-1
SR-05000001749-2
BRD-K47869605-001-05-6
BRD-K47869605-001-18-9
BRD-K47869605-001-32-0
Z759291658
(10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0?,?.0??,??]hexadeca-1(9),2,7-trien-12-one
(10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.03,7.011,15]hexadeca-1,3(7),8-trien-12-one
(5R,5aR,8aR,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[6,5-f][1,3]benzodioxol-8-one
(5R,5aR,8aR,9R)-5-oxidanyl-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
11016-28-7
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-(5.alpha.,5a.beta.,8a.alpha.,9.alpha.)]
Furo[3',4':6,7]naphtha[2,3-d]-1,3-dioxol-6(5?H)-one, 5,8,8?,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)
Furo[3',7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, [5R-(5.alpha.,5a.beta.,8a.alpha.,9.alpha.)]-
Naphtho[2,3-dioxole-6-carboxylic acid, 5,6,7,8-tetrahydro-8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl-, .gamma.-lactone