Podophyllotoxin

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  • Identifiers

    CAS number
    518-28-5

    Molecular formula
    C22H22O8

    SMILES
    COC1=CC(=CC(=C1OC)OC)[C@H]2[C@@H]3[C@H](COC3=O)[C@H](C4=CC5=C(C=C24)OCO5)O

    Safety labels

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Vanilla 51.57%
    Sweet 45.94%
    Spicy 43.23%
    Odorless 34.66%
    Powdery 32.65%
    Balsamic 30.56%
    Phenolic 30.1%
    Floral 30.08%
    Creamy 29.17%
    Warm 21.73%

     

    Flavor
    Bitter 93.57%
    Bland 28.02%
    Sweet-like 20.63%
    Cedarleaf 20.1%
    Parsley 19.89%
    Lovage 18.84%
    Ripe apricot 18.16%
    Eugenol 17.81%
    Red fruit 17.63%
    Cereal 17.2%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.0

    pKa est.
    5.11 (weak acid)

    Molecular weight
    414.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1331°C

    Melting point expt.

    • 228 °C
    • 114-118 °C
    • 183 °C
    • MP: 114-118 °C (effervescence)

    Flash point

    • 229.27 ˚C est.

    Solubility expt.

    • 100 mg/L (at 25 °C)
    • Insoluble in ethyl ether, ligroin; slightly soluble in water; soluble in acetone, benzene; very soluble in ethanol, chloroform.
    • In water, 150 mg/L at 25 °C /Estimated/
    • 1.14e-01 g/L

  • Synonyms

    • podophyllotoxin
    • Podofilox
    • 518-28-5
    • Condylox
    • (-)-Podophyllotoxin
    • Podophyllinic acid lactone
    • Podophyllotoxin 7
    • Wartec
    • Warticon
    • Podofilm
    • NSC-24818
    • (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
    • DTXSID3045645
    • (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
    • L36H50F353
    • DTXCID1025645
    • CHEBI:50305
    • 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))-
    • (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
    • (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
    • (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-(2)benzofuro(5,6-f)(1,3)benzodioxol-8-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
    • RefChem:56693
    • GlyTouCan:G88801WQ
    • 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
    • G88801WQ
    • 208-250-4
    • Condyline
    • Podofilox [USAN]
    • MFCD00075290
    • NSC24818
    • CHEMBL61
    • MLS000069495
    • (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)-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
    • Podofilox (USAN)
    • (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-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)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
    • NCGC00022001-05
    • SMR000059121
    • NSC 24818
    • 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)-
    • Podophilox
    • (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
    • CCRIS 565
    • Podocon-25
    • HSDB 7238
    • SR-05000001749
    • MLS002702981
    • EINECS 208-250-4
    • Podofillina
    • Podophylotoxin
    • podophyllotoxine
    • AI3-50456
    • Condyline;
    • Mayapple isolate
    • Condylox;
    • UNII-L36H50F353
    • Condylox (TN)
    • CAS-518-28-5
    • Podophyllotoxin CRS
    • Prestwick_1018
    • Podofilox (Standard)
    • Podofillina [Italian]
    • Podophyllotoxin (BAN)
    • Spectrum_000199
    • Etoposide EP Impurity M
    • 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
    • orb1309699
    • PODOFILOX [ORANGE BOOK]
    • PODOPHYLLOTOXIN [MART.]
    • PODOPHYLLOTOXIN [WHO-DD]
    • SCHEMBL29351029
    • UPCMLD-DP035:001
    • UPCMLD-DP035:002
    • BCBcMAP01_000165
    • GTPL13598
    • HMS500O14
    • KBio1_000292
    • KBio2_000679
    • KBio2_003247
    • KBio2_005815
    • NINDS_000292
    • GLXC-10126
    • HMS1570M06
    • HMS2093P16
    • HMS2097M06
    • HMS2235A23
    • HMS3259J19
    • HMS3714M06
    • Pharmakon1600-02300332
    • ALBB-020906
    • BB_NC-01063
    • 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
    • 518-28-5

  • Applications

    Podophyllotoxin (CAS 518-28-5) is a natural lignan that serves as a key building block in medicinal chemistry and is widely used as a starting material for the semisynthesis of anticancer agents such as etoposide and teniposide, as well as for preparing other podophyllotoxin derivatives. It is also employed as an active component in topical dermatology formulations containing podophyllotoxin, used for certain skin conditions including external anogenital warts, in compliance with regulatory controls. In pharmaceutical research, it acts as a lead compound to explore mechanisms related to topoisomerase II inhibition and cytoskeleton effects, and is used as a reference standard in analytical methods. Additionally, it is used as an intermediate to access other lignan bioactive compounds in chemical synthesis and as a research tool in drug development projects.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.88
    methanol 1.39
    isopropanol 0.79
    water 0.09
    ethyl acetate 3.63
    n-propanol 0.79
    acetone 9.09
    n-butanol 0.76
    acetonitrile 5.61
    DMF 15.45
    toluene 0.69
    isobutanol 0.66
    1,4-dioxane 7.01
    methyl acetate 4.44
    THF 8.92
    2-butanone 4.46
    n-pentanol 0.9
    sec-butanol 0.51
    n-hexane 0.03
    ethylene glycol 1.45
    NMP 12.08
    cyclohexane 0.08
    DMSO 33.16
    n-butyl acetate 4.15
    n-octanol 2.04
    chloroform 6.63
    n-propyl acetate 3.81
    acetic acid 11.02
    dichloromethane 6.24
    cyclohexanone 9.96
    propylene glycol 0.48
    isopropyl acetate 3.29
    DMAc 23.38
    2-ethoxyethanol 5.66
    isopentanol 1.11
    n-heptane 0.08
    ethyl formate 4.52
    1,2-dichloroethane 4.39
    n-hexanol 1.2
    2-methoxyethanol 6.71
    isobutyl acetate 3.23
    tetrachloromethane 1.25
    n-pentyl acetate 5.71
    transcutol 12.52
    n-heptanol 2.16
    ethylbenzene 0.5
    MIBK 3.6
    2-propoxyethanol 8.54
    tert-butanol 1.28
    MTBE 0.85
    2-butoxyethanol 8.08
    propionic acid 2.68
    o-xylene 0.68
    formic acid 7.84
    diethyl ether 1.12
    m-xylene 0.59
    p-xylene 0.9
    chlorobenzene 1.8
    dimethyl carbonate 6.71
    n-octane 0.1
    formamide 11.2
    cyclopentanone 11.08
    2-pentanone 3.45
    anisole 1.8
    cyclopentyl methyl ether 1.66
    gamma-butyrolactone 14.21
    1-methoxy-2-propanol 3.81
    pyridine 5.42
    3-pentanone 3.14
    furfural 15.24
    n-dodecane 0.14
    diethylene glycol 11.53
    diisopropyl ether 0.48
    tert-amyl alcohol 0.85
    acetylacetone 10.73
    n-hexadecane 0.17
    acetophenone 4.74
    methyl propionate 3.76
    isopentyl acetate 4.65
    trichloroethylene 9.55
    n-nonanol 2.51
    cyclohexanol 0.99
    benzyl alcohol 2.9
    2-ethylhexanol 1.26
    isooctanol 2.19
    dipropyl ether 1.4
    1,2-dichlorobenzene 2.58
    ethyl lactate 3.77
    propylene carbonate 8.11
    n-methylformamide 6.84
    2-pentanol 0.42
    n-pentane 0.03
    1-propoxy-2-propanol 5.13
    1-methoxy-2-propyl acetate 7.18
    2-(2-methoxypropoxy) propanol 9.03
    mesitylene 0.47
    ε-caprolactone 7.71
    p-cymene 0.99
    epichlorohydrin 11.67
    1,1,1-trichloroethane 3.48
    2-aminoethanol 1.23
    morpholine-4-carbaldehyde 17.2
    sulfolane 20.31
    2,2,4-trimethylpentane 0.04
    2-methyltetrahydrofuran 2.33
    n-hexyl acetate 5.29
    isooctane 0.03
    2-(2-butoxyethoxy)ethanol 9.35
    sec-butyl acetate 2.27
    tert-butyl acetate 3.9
    decalin 0.09
    glycerin 2.8
    diglyme 18.46
    acrylic acid 4.88
    isopropyl myristate 2.98
    n-butyric acid 3.73
    acetyl acetate 6.36
    di(2-ethylhexyl) phthalate 4.41
    ethyl propionate 2.94
    nitromethane 29.09
    1,2-diethoxyethane 5.05
    benzonitrile 5.26
    trioctyl phosphate 3.61
    1-bromopropane 0.94
    gamma-valerolactone 22.62
    n-decanol 1.85
    triethyl phosphate 3.79
    4-methyl-2-pentanol 0.66
    propionitrile 3.37
    vinylene carbonate 10.11
    1,1,2-trichlorotrifluoroethane 16.75
    DMS 6.27
    cumene 0.52
    2-octanol 1.4
    2-hexanone 3.97
    octyl acetate 3.89
    limonene 1.04
    1,2-dimethoxyethane 10.49
    ethyl orthosilicate 3.04
    tributyl phosphate 4.09
    diacetone alcohol 6.05
    N,N-dimethylaniline 1.66
    acrylonitrile 6.66
    aniline 1.53
    1,3-propanediol 2.57
    bromobenzene 1.57
    dibromomethane 3.19
    1,1,2,2-tetrachloroethane 6.87
    2-methyl-cyclohexyl acetate 4.39
    tetrabutyl urea 6.87
    diisobutyl methanol 1.12
    2-phenylethanol 4.08
    styrene 0.59
    dioctyl adipate 5.38
    dimethyl sulfate 12.41
    ethyl butyrate 3.49
    methyl lactate 4.25
    butyl lactate 5.58
    diethyl carbonate 3.43
    propanediol butyl ether 4.92
    triethyl orthoformate 3.31
    p-tert-butyltoluene 0.82
    methyl 4-tert-butylbenzoate 8.11
    morpholine 5.2
    tert-butylamine 0.5
    n-dodecanol 1.43
    dimethoxymethane 9.44
    ethylene carbonate 8.79
    cyrene 10.42
    2-ethoxyethyl acetate 9.17
    2-ethylhexyl acetate 3.52
    1,2,4-trichlorobenzene 3.25
    4-methylpyridine 4.01
    dibutyl ether 1.96
    2,6-dimethyl-4-heptanol 1.12
    DEF 5.7
    dimethyl isosorbide 14.34
    tetrachloroethylene 5.89
    eugenol 9.1
    triacetin 9.2
    span 80 5.83
    1,4-butanediol 1.51
    1,1-dichloroethane 2.42
    2-methyl-1-pentanol 1.07
    methyl formate 7.9
    2-methyl-1-butanol 0.74
    n-decane 0.22
    butyronitrile 2.53
    3,7-dimethyl-1-octanol 1.89
    1-chlorooctane 1.06
    1-chlorotetradecane 0.58
    n-nonane 0.15
    undecane 0.17
    tert-butylcyclohexane 0.07
    cyclooctane 0.04
    cyclopentanol 1.08
    tetrahydropyran 2.27
    tert-amyl methyl ether 0.77
    2,5,8-trioxanonane 15.42
    1-hexene 0.17
    2-isopropoxyethanol 4.28
    2,2,2-trifluoroethanol 11.13
    methyl butyrate 4.07

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 No restriction Category 7A
Rinse-off products applied to the hair with some hand contact
 No restriction
Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
 No restriction
Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
 No restriction
Category 4
Products related to fine fragrance
 No restriction Category 9
Products with body and hand exposure, primarily rinse off
 No restriction
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 No restriction Category 10A
Household care products with mostly hand contact
 No restriction
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 No restriction Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 No restriction
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 No restriction Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 No restriction
Category 5D
Baby Creams, baby Oils and baby talc
 No restriction Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 No restriction
Category 6
Products with oral and lip exposure
 No restriction Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction