Etoposide

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  • Identifiers

    CAS number
    33419-42-0

    Molecular formula
    C29H32O13

    SMILES
    C[C@@H]1OC[C@@H]2[C@@H](O1)[C@@H]([C@H]([C@@H](O2)O[C@H]3[C@H]4COC(=O)[C@@H]4[C@@H](C5=CC6=C(C=C35)OCO6)C7=CC(=C(C(=C7)OC)O)OC)O)O

    Safety labels

    Irritant
    Irritant

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Odorless 57.03%
    Vanilla 43.65%
    Sweet 30.54%
    Spicy 30.44%
    Creamy 23.78%
    Milky 22.6%
    Powdery 20.27%
    Phenolic 20.0%
    Balsamic 19.29%
    Dairy 18.36%

     

    Flavor
    Bitter 84.69%
    Bland 30.01%
    Sweet-like 23.98%
    Cedarleaf 20.61%
    Parsley 19.57%
    Fatty 19.09%
    Lovage 18.92%
    Odorless 18.64%
    Naphthalic 18.62%
    Cereal 18.44%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.6

    pKa est.
    5.49 (weak acid)

    Molecular weight
    588.6 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    3069°C

    Melting point expt.

    • 236-251 °C
    • 236 - 251 °C

    Flash point

    • 217.28 ˚C est.

    Solubility expt.

    • Sparingly soluble
    • Very soluble in methanol, chloroform; slightly soluble in ethanol, sparingly soluble in water.
    • Sol in alc: approx 0.76 mg/ml
    • Water solubility: approx 0.08 mg/mL
    • 9.78e-01 g/L

  • Synonyms

    • etoposide
    • 33419-42-0
    • VePesid
    • Toposar
    • trans-Etoposide
    • (-)-Etoposide
    • Lastet
    • Etoposido
    • Etoposidum
    • Eposin
    • Sintopozid
    • VP-16-213
    • VP 16-213
    • NSC-141540
    • 4-Demethylepipodophyllotoxin beta-D-ethylideneglucoside
    • VP 16
    • EPEG
    • VP 16213
    • 6PLQ3CP4P3
    • 4'-Demethylepipodophyllotoxin 9-(4,6-O-(R)-ethylidene-beta-D-glucopyranoside)
    • NSC 141540
    • DTXSID5023035
    • CHEBI:4911
    • DTXCID601473876
    • Eposide
    • 4'-Demethylepipodophyllotoxin 9-(4,6-O-ethylidene-beta-D-glucopyranoside)
    • (5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
    • 9-((4,6-O-Ethylidine-beta-D-glucopyranosyl)oxy)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,4-dimethyloxyphenyl)furo(3',4'':6,7)naptho-(2,3-d)-1,3-dioxol-6(5aH)-one
    • Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one, 9-((4,6-O-(1R)-ethylidene-beta-D-glucopyranosyl)oxy)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-, (5R,5aR,8aR,9S)-
    • Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one-, 9-((4,6-O-ethylidene-beta-D-glucopyranosyl)oxy)5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl), (5R-(5alpha,5abeta,8aalpha,9beta(R*)))-
    • NSC141540
    • (10R,11R,15R,16S)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-one
    • Etoposide Teva
    • Teva, Etoposide
    • alpha-D-Glucopyranosyl Isomer Etoposide
    • (10R,11R,15R,16S)-16-(((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano(3,2-d)(1,3)dioxin-6-yl)oxy)-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo(7.7.0.0^(3,7).0^(11,15))hexadeca-1(9),2,7-trien-12-one
    • (5S,5aR,8aR,9R)-5-(((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano(3,2-d)(1,3)dioxin-6-yl)oxy)-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-(2)benzofuro(6,5-f)(1,3)benzodioxol-8-one
    • Eto GRY
    • RefChem:56691
    • Demethyl Epipodophyllotoxin Ethylidine Glucoside
    • L01CB01
    • Etoposide, alpha D Glucopyranosyl
    • VP 16 213
    • (10R,11R,15R,16S)-16-(((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano(3,2-d)(1,3)dioxin-6-yl)oxy)-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo(7.7.0.03,7.011,15)hexadeca-1,3(7),8-trien-12-one
    • (5R,5aR,8aR,9S)-9-((4,6-O-(1R)-Ethylidene-beta-D-glucopyranosyl)oxy)-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
    • 251-509-1
    • 9-((4,6-O-Ethylidene-beta-D-glucopyranosyl)oxy)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one
    • Zuyeyidal
    • Etoposidum [INN-Latin]
    • VP-16
    • Etoposide (VP16)
    • Vepesid J
    • Etoposide (VP-16)
    • VP 16 (pharmaceutical)
    • Epipodophyllotoxin VP-16213
    • CHEMBL44657
    • NK 171
    • Etosid
    • C29H32O13
    • Etoposido [INN-Spanish]
    • (5R,5aR,8aR,9S)-9-(((4aR,6R,7R,8R,8aS)-7,8-Dihydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)-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
    • (5S,5aR,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl 4,6-O-[(1R)-ethylidene]-beta-D-glucopyranoside
    • Etopophos (phosphate salt)
    • Etopol
    • (5R,5aR,8aR,9S)-9-(((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)-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
    • SMR000112002
    • ol-6(8H)-one
    • CCRIS 2392
    • HSDB 6517
    • VePESID (TN)
    • EINECS 251-509-1
    • UNII-6PLQ3CP4P3
    • 4'-Demethylepipodophyllotoxin ethylidene-.beta.-D-glucoside
    • Vespid
    • Etopophos;
    • Abiposid;
    • Vepeside;
    • Amizide;
    • Citodox;
    • Toposar;
    • Vepesid;
    • Etoposide RS
    • Etoposide CRS
    • Exitop;
    • NCGC00016821-01
    • (5S,5aR,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol -5-yl 4,6-O-[(1R)-ethylidene]-beta-D-glucopyranoside
    • EVP
    • Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 9-[[4,6-O-(1R)-ethylidene-.beta.-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-, (5R,5aR,8aR,9S)-
    • Demethylepipodophyllotoxin-beta-D-ethylideneglucoside
    • 4'-O-Demethyl-1-O-(4,6-O-ethylidene-beta-D-glucopyranosyl)epipodophyllotoxin
    • Epipodophyllotoxin, 4'-demethyl-, 9-(4,6-O-ethylidene-beta-D-glucopyranoside)
    • CAS-33419-42-0
    • Etoposide (Standard)
    • Etoposide [USAN:USP:INN:BAN:JAN]
    • Etoposide; VP-16
    • CPD000112002
    • Epipodophyllotoxin-beta-D-ethyliden-glucoside, 4'-demethyl-
    • ETOPOSIDE [INN]
    • ETOPOSIDE [JAN]
    • ETOPOSIDE [MI]
    • ETOPOSIDE [HSDB]
    • ETOPOSIDE [IARC]
    • ETOPOSIDE [USAN]
    • Prestwick3_000396
    • ETOPOSIDE [VANDF]
    • ETOPOSIDE [MART.]
    • Epipodophyllotoxin, 4'-demethyl-, 4,6-O-ethylidene-beta-D-glucopyranoside
    • ETOPOSIDE [USP-RS]
    • ETOPOSIDE [WHO-DD]
    • ETOPOSIDE [WHO-IP]
    • SCHEMBL4259
    • BSPBio_000611
    • 9-((4,6-O-Ethylidene-beta-D-glucopyranosyl)oxy)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one, (5R-(5alpha,5abeta,8aalpha,9beta(R*)))-
    • 9-((4,6-O-Ethylidine-beta-D-glucopyranosyl)oxy)-5,8,8a,9-tetrahydro-5-(4- hydroxy-3,4-dimethyloxyphenyl)furo (3',4'':6,7) naptho-(2,3-d)-1,3-dioxol-6 (5aH)-one
    • MLS000049957
    • MLS001074951
    • MLS001424283
    • MLS002153463
    • MLS002207239
    • MLS002222184
    • Etoposide - Bio-X trade mark
    • Etoposide (JP18/USP/INN)
    • BPBio1_000673
    • GTPL6815
    • orb1310906
    • ETOPOSIDE [EP IMPURITY]
    • ETOPOSIDE [ORANGE BOOK]
    • 33419-42-0

  • Applications

    Etoposide (CAS 33419-42-0) is used in pharmaceuticals as an anticancer chemotherapy agent, functioning as a topoisomerase II inhibitor in cancer treatment regimens; in pharmaceutical research and development, it serves as a reference for formulation assessment, dose optimization, and process standardization for cytotoxic drugs; in analytical chemistry and quality control, etoposide is used as a reference standard and calibration material in HPLC/LC-MS methods to quantify content and assess purity; as a research tool, it is employed in in vitro studies to explore the mechanism of action and consequences of topoisomerase II inhibition; as a podophyllotoxin-related compound, it is handled under safety and regulatory requirements for cytotoxic pharmaceuticals.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 2.47
    methanol 6.15
    isopropanol 2.1
    water 0.11
    ethyl acetate 6.05
    n-propanol 2.7
    acetone 21.64
    n-butanol 2.19
    acetonitrile 7.27
    DMF 45.53
    toluene 0.98
    isobutanol 1.62
    1,4-dioxane 17.47
    methyl acetate 8.03
    THF 30.25
    2-butanone 11.17
    n-pentanol 1.71
    sec-butanol 1.46
    n-hexane 0.03
    ethylene glycol 4.32
    NMP 35.79
    cyclohexane 0.08
    DMSO 87.25
    n-butyl acetate 2.51
    n-octanol 2.7
    chloroform 7.95
    n-propyl acetate 3.4
    acetic acid 33.72
    dichloromethane 7.31
    cyclohexanone 16.08
    propylene glycol 2.56
    isopropyl acetate 3.69
    DMAc 52.04
    2-ethoxyethanol 13.37
    isopentanol 1.71
    n-heptane 0.08
    ethyl formate 8.32
    1,2-dichloroethane 5.02
    n-hexanol 1.12
    2-methoxyethanol 21.83
    isobutyl acetate 1.93
    tetrachloromethane 1.02
    n-pentyl acetate 5.57
    transcutol 22.82
    n-heptanol 2.23
    ethylbenzene 0.38
    MIBK 3.73
    2-propoxyethanol 10.9
    tert-butanol 2.06
    MTBE 1.44
    2-butoxyethanol 9.68
    propionic acid 7.1
    o-xylene 0.64
    formic acid 17.86
    diethyl ether 2.15
    m-xylene 0.53
    p-xylene 0.57
    chlorobenzene 1.66
    dimethyl carbonate 11.12
    n-octane 0.07
    formamide 19.66
    cyclopentanone 27.89
    2-pentanone 7.71
    anisole 1.85
    cyclopentyl methyl ether 3.55
    gamma-butyrolactone 30.18
    1-methoxy-2-propanol 11.83
    pyridine 9.61
    3-pentanone 5.53
    furfural 25.0
    n-dodecane 0.1
    diethylene glycol 12.93
    diisopropyl ether 0.45
    tert-amyl alcohol 1.47
    acetylacetone 17.24
    n-hexadecane 0.12
    acetophenone 3.98
    methyl propionate 7.17
    isopentyl acetate 2.26
    trichloroethylene 12.97
    n-nonanol 2.94
    cyclohexanol 1.71
    benzyl alcohol 3.12
    2-ethylhexanol 0.81
    isooctanol 1.66
    dipropyl ether 1.44
    1,2-dichlorobenzene 1.78
    ethyl lactate 4.17
    propylene carbonate 9.81
    n-methylformamide 20.32
    2-pentanol 0.99
    n-pentane 0.04
    1-propoxy-2-propanol 6.1
    1-methoxy-2-propyl acetate 6.19
    2-(2-methoxypropoxy) propanol 9.61
    mesitylene 0.3
    ε-caprolactone 12.42
    p-cymene 0.44
    epichlorohydrin 24.94
    1,1,1-trichloroethane 3.39
    2-aminoethanol 4.2
    morpholine-4-carbaldehyde 42.59
    sulfolane 48.14
    2,2,4-trimethylpentane 0.04
    2-methyltetrahydrofuran 5.76
    n-hexyl acetate 5.83
    isooctane 0.02
    2-(2-butoxyethoxy)ethanol 13.34
    sec-butyl acetate 1.78
    tert-butyl acetate 3.34
    decalin 0.05
    glycerin 8.97
    diglyme 22.85
    acrylic acid 11.55
    isopropyl myristate 2.21
    n-butyric acid 8.23
    acetyl acetate 7.79
    di(2-ethylhexyl) phthalate 3.31
    ethyl propionate 2.84
    nitromethane 59.23
    1,2-diethoxyethane 6.16
    benzonitrile 4.08
    trioctyl phosphate 2.74
    1-bromopropane 1.2
    gamma-valerolactone 60.59
    n-decanol 1.99
    triethyl phosphate 1.87
    4-methyl-2-pentanol 0.71
    propionitrile 4.41
    vinylene carbonate 11.94
    1,1,2-trichlorotrifluoroethane 25.78
    DMS 5.53
    cumene 0.27
    2-octanol 1.57
    2-hexanone 4.4
    octyl acetate 3.68
    limonene 0.59
    1,2-dimethoxyethane 19.7
    ethyl orthosilicate 1.57
    tributyl phosphate 2.53
    diacetone alcohol 7.48
    N,N-dimethylaniline 1.41
    acrylonitrile 8.7
    aniline 2.23
    1,3-propanediol 7.63
    bromobenzene 1.33
    dibromomethane 3.26
    1,1,2,2-tetrachloroethane 8.46
    2-methyl-cyclohexyl acetate 2.35
    tetrabutyl urea 5.06
    diisobutyl methanol 0.57
    2-phenylethanol 2.76
    styrene 0.46
    dioctyl adipate 4.26
    dimethyl sulfate 20.21
    ethyl butyrate 2.41
    methyl lactate 8.81
    butyl lactate 5.87
    diethyl carbonate 1.91
    propanediol butyl ether 9.68
    triethyl orthoformate 2.43
    p-tert-butyltoluene 0.37
    methyl 4-tert-butylbenzoate 6.19
    morpholine 14.89
    tert-butylamine 0.6
    n-dodecanol 1.35
    dimethoxymethane 22.75
    ethylene carbonate 9.94
    cyrene 12.76
    2-ethoxyethyl acetate 10.2
    2-ethylhexyl acetate 1.64
    1,2,4-trichlorobenzene 2.73
    4-methylpyridine 5.8
    dibutyl ether 2.0
    2,6-dimethyl-4-heptanol 0.57
    DEF 11.0
    dimethyl isosorbide 13.04
    tetrachloroethylene 5.68
    eugenol 6.44
    triacetin 9.38
    span 80 8.06
    1,4-butanediol 3.59
    1,1-dichloroethane 3.15
    2-methyl-1-pentanol 1.24
    methyl formate 20.7
    2-methyl-1-butanol 1.44
    n-decane 0.17
    butyronitrile 3.49
    3,7-dimethyl-1-octanol 1.63
    1-chlorooctane 0.87
    1-chlorotetradecane 0.38
    n-nonane 0.12
    undecane 0.13
    tert-butylcyclohexane 0.03
    cyclooctane 0.04
    cyclopentanol 2.93
    tetrahydropyran 5.46
    tert-amyl methyl ether 1.2
    2,5,8-trioxanonane 17.7
    1-hexene 0.15
    2-isopropoxyethanol 6.82
    2,2,2-trifluoroethanol 16.54
    methyl butyrate 4.43

    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