Camptothecin

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  • Identifiers

    CAS number
    7689-03-4

    Molecular formula
    C20H16N2O4

    SMILES
    CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=CC5=CC=CC=C5N=C4C3=C2)O

    Safety labels

    Acute Toxic
    Acute Toxic

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Odorless 48.26%
    Sweet 32.63%
    Vanilla 25.26%
    Fruity 24.31%
    Powdery 24.1%
    Bitter 23.63%
    Burnt 22.13%
    Grape 21.25%
    Milky 20.84%
    Caramellic 20.68%

     

    Flavor
    Bitter 97.46%
    Odorless 23.72%
    Bland 22.12%
    Sweet-like 19.52%
    Cedarleaf 18.97%
    Lovage 18.33%
    Indole 17.82%
    Very strong 17.78%
    Parsley 17.61%
    Nitrile 17.61%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.0

    pKa est.
    4.67 (weak acid)

    Molecular weight
    348.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1156°C

    Melting point expt.

    • 275-277 °C

    Flash point

    • 272.07 ˚C est.

  • Synonyms

    • camptothecin
    • Camptothecine
    • 7689-03-4
    • (S)-(+)-Camptothecin
    • (+)-Camptothecin
    • d-Camptothecin
    • 20(S)-Camptothecine
    • (+)-Camptothecine
    • 21,22-Secocamptothecin-21-oic acid lactone
    • NSC94600
    • NSC-94600
    • XT3Z54Z28A
    • DTXSID0030956
    • (4S)-4-ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
    • (19S)-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione
    • CHEBI:27656
    • 1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-, (S)-
    • (4S)-4-ETHYL-4-HYDROXY-1H-PYRANO(3',4':6,7)INDOLIZINO(1,2-B)QUINOLINE-3,14(4H,12H)-DIONE
    • (19S)-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo(11.8.0.02,11.04,9.015,20)henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione
    • 1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-, (S)-
    • 20-(S)-camptothecine
    • RefChem:388854
    • DTXCID8010956
    • 21, 22-Secocamptothecin-21-oic acid lactone
    • (S)-4-ethyl-4-hydroxy-1H-pyrano-(3',4':6,7)indolozino(1,2-b)quinoline-3,14(4H,12H)-dione
    • 1H-Pyrano(3',3'.6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4-ethyl-4hydroxy-(S)-
    • Campathecin
    • MFCD00081076
    • (S)-4-ethyl-4-hydroxy-1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
    • Camptothecine (S,+)
    • CHEMBL65
    • MLS000766223
    • (19S)-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione
    • M01564
    • (S)-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione
    • (s)-camptothecine
    • (S)-Camptothecin
    • 1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-, (4S)-
    • 1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-, (4S)-
    • 20(S)-Camptothecin
    • 4-ETHYL-4-HYDROXY-1,12-DIHYDRO-4H-2-OXA-6,12A-DIAZA-DIBENZO[B,H]FLUORENE-3,13-DIONE
    • SR-01000075798
    • SR-01000597379
    • d-camptothecine
    • (S)-4-ethyl-4-hydroxy-1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione
    • (S)-4-Ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-(4H,12H)-dione
    • Prestwick_102
    • Camptothecine (8CI)
    • Spectrum_000299
    • Tocris-1100
    • SpecPlus_000712
    • Prestwick0_000200
    • Prestwick1_000200
    • Prestwick2_000200
    • Prestwick3_000200
    • Spectrum2_000903
    • Spectrum3_001203
    • Spectrum4_000738
    • Spectrum5_001126
    • CAMPTOTHECIN [MI]
    • Lopac-C-9911
    • SCHEMBL6038
    • UNII-XT3Z54Z28A
    • Lopac0_000341
    • BSPBio_000159
    • BSPBio_002586
    • KBioGR_001036
    • KBioSS_000779
    • KBioSS_002283
    • cid_24360
    • CAMPTOTHECIN [WHO-DD]
    • DivK1c_000826
    • DivK1c_006808
    • SPECTRUM1502232
    • SPBio_000746
    • SPBio_002080
    • BPBio1_000175
    • CCRIS 8162
    • orb1309690
    • SCHEMBL29351099
    • SCHEMBL29360250
    • HMS502J08
    • KBio1_000826
    • KBio1_001752
    • KBio2_000779
    • KBio2_003347
    • KBio2_005915
    • KBio3_002086
    • 4-Ethyl-4-hydroxy-1H-pyrano-[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
    • NINDS_000826
    • Bio1_000400
    • Bio1_000889
    • Bio1_001378
    • GLXC-10346
    • HMS1568H21
    • HMS1921N08
    • HMS2089F08
    • HMS2095H21
    • HMS3261E03
    • HMS3414J17
    • HMS3654D13
    • HMS3678J15
    • HMS3712H21
    • BB_NC-00996
    • MSK40312
    • Tox21_500341
    • AC-202
    • BBL033963
    • BDBM50008923
    • CCG-40255
    • EBC-14151
    • GR-301
    • NSC 94600
    • s1288
    • STK801886
    • AKOS004119861
    • Camptothecin; Irinotecan EP Impurity D
    • DB04690
    • FC15450
    • KS-5235
    • LP00341
    • SDCCGMLS-0066688.P001
    • SDCCGSBI-0050329.P003
    • BRN 0631069
    • CAS-2114454
    • IDI1_000826
    • NCGC00015290-01
    • 7689-03-4

  • Applications

    Camptothecin (CAS 7689-03-4) is a natural alkaloid primarily used as a pharmaceutical lead compound in anticancer drug development targeting topoisomerase I, and as the starting point for semi-synthetic derivatives such as topotecan and irinotecan. It is also used as a reference reagent in topoisomerase I mechanism studies and basic mechanistic work, and as a synthetic intermediate to access camptothecin derivatives. Additionally, camptothecin is used in laboratory research and in structure-activity relationship (SAR) evaluations of derivatives to optimize medicinal chemistry properties. In manufacturing and supply chains, it is sourced as a natural product and used as reference material for large-scale synthesis and preclinical screening.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.11
    methanol 0.18
    isopropanol 0.15
    water 0.0
    ethyl acetate 1.49
    n-propanol 0.15
    acetone 1.15
    n-butanol 0.25
    acetonitrile 0.51
    DMF 2.7
    toluene 1.36
    isobutanol 0.18
    1,4-dioxane 2.33
    methyl acetate 1.08
    THF 3.14
    2-butanone 1.37
    n-pentanol 0.25
    sec-butanol 0.16
    n-hexane 0.02
    ethylene glycol 0.2
    NMP 3.13
    cyclohexane 0.03
    DMSO 1.58
    n-butyl acetate 1.5
    n-octanol 0.46
    chloroform 1.51
    n-propyl acetate 1.24
    acetic acid 1.88
    dichloromethane 1.91
    cyclohexanone 3.79
    propylene glycol 0.11
    isopropyl acetate 2.04
    DMAc 6.51
    2-ethoxyethanol 1.44
    isopentanol 0.53
    n-heptane 0.04
    ethyl formate 0.82
    1,2-dichloroethane 1.32
    n-hexanol 0.4
    2-methoxyethanol 2.02
    isobutyl acetate 1.23
    tetrachloromethane 0.26
    n-pentyl acetate 2.55
    transcutol 10.75
    n-heptanol 0.76
    ethylbenzene 0.6
    MIBK 2.06
    2-propoxyethanol 2.97
    tert-butanol 0.35
    MTBE 0.45
    2-butoxyethanol 3.74
    propionic acid 0.62
    o-xylene 1.01
    formic acid 1.24
    diethyl ether 0.47
    m-xylene 1.17
    p-xylene 0.8
    chlorobenzene 1.16
    dimethyl carbonate 3.0
    n-octane 0.04
    formamide 1.74
    cyclopentanone 3.66
    2-pentanone 1.46
    anisole 1.47
    cyclopentyl methyl ether 1.23
    gamma-butyrolactone 3.86
    1-methoxy-2-propanol 1.68
    pyridine 3.26
    3-pentanone 1.5
    furfural 6.68
    n-dodecane 0.05
    diethylene glycol 3.72
    diisopropyl ether 0.39
    tert-amyl alcohol 0.32
    acetylacetone 5.18
    n-hexadecane 0.06
    acetophenone 2.8
    methyl propionate 1.51
    isopentyl acetate 2.53
    trichloroethylene 3.75
    n-nonanol 0.68
    cyclohexanol 0.48
    benzyl alcohol 1.56
    2-ethylhexanol 0.55
    isooctanol 0.94
    dipropyl ether 0.72
    1,2-dichlorobenzene 1.62
    ethyl lactate 1.5
    propylene carbonate 2.57
    n-methylformamide 0.88
    2-pentanol 0.24
    n-pentane 0.02
    1-propoxy-2-propanol 1.97
    1-methoxy-2-propyl acetate 4.75
    2-(2-methoxypropoxy) propanol 5.42
    mesitylene 0.77
    ε-caprolactone 3.16
    p-cymene 0.91
    epichlorohydrin 4.0
    1,1,1-trichloroethane 1.04
    2-aminoethanol 0.2
    morpholine-4-carbaldehyde 5.75
    sulfolane 4.73
    2,2,4-trimethylpentane 0.03
    2-methyltetrahydrofuran 1.02
    n-hexyl acetate 2.21
    isooctane 0.03
    2-(2-butoxyethoxy)ethanol 5.8
    sec-butyl acetate 1.38
    tert-butyl acetate 2.98
    decalin 0.05
    glycerin 0.9
    diglyme 12.11
    acrylic acid 1.16
    isopropyl myristate 1.58
    n-butyric acid 1.3
    acetyl acetate 3.08
    di(2-ethylhexyl) phthalate 2.93
    ethyl propionate 1.58
    nitromethane 3.99
    1,2-diethoxyethane 2.87
    benzonitrile 2.08
    trioctyl phosphate 1.57
    1-bromopropane 0.4
    gamma-valerolactone 7.75
    n-decanol 0.53
    triethyl phosphate 2.07
    4-methyl-2-pentanol 0.43
    propionitrile 0.71
    vinylene carbonate 3.69
    1,1,2-trichlorotrifluoroethane 5.24
    DMS 3.97
    cumene 0.54
    2-octanol 0.48
    2-hexanone 1.2
    octyl acetate 1.65
    limonene 0.77
    1,2-dimethoxyethane 3.49
    ethyl orthosilicate 2.04
    tributyl phosphate 1.77
    diacetone alcohol 3.5
    N,N-dimethylaniline 1.32
    acrylonitrile 1.44
    aniline 1.39
    1,3-propanediol 0.62
    bromobenzene 1.26
    dibromomethane 0.9
    1,1,2,2-tetrachloroethane 2.27
    2-methyl-cyclohexyl acetate 2.39
    tetrabutyl urea 2.87
    diisobutyl methanol 0.73
    2-phenylethanol 2.65
    styrene 0.62
    dioctyl adipate 2.74
    dimethyl sulfate 4.49
    ethyl butyrate 1.76
    methyl lactate 2.0
    butyl lactate 2.64
    diethyl carbonate 1.91
    propanediol butyl ether 1.88
    triethyl orthoformate 2.25
    p-tert-butyltoluene 0.88
    methyl 4-tert-butylbenzoate 6.29
    morpholine 1.48
    tert-butylamine 0.17
    n-dodecanol 0.43
    dimethoxymethane 3.33
    ethylene carbonate 2.74
    cyrene 4.55
    2-ethoxyethyl acetate 5.6
    2-ethylhexyl acetate 1.84
    1,2,4-trichlorobenzene 2.38
    4-methylpyridine 2.5
    dibutyl ether 0.78
    2,6-dimethyl-4-heptanol 0.73
    DEF 2.18
    dimethyl isosorbide 9.66
    tetrachloroethylene 2.16
    eugenol 6.77
    triacetin 5.06
    span 80 3.32
    1,4-butanediol 0.27
    1,1-dichloroethane 0.66
    2-methyl-1-pentanol 0.5
    methyl formate 1.11
    2-methyl-1-butanol 0.36
    n-decane 0.07
    butyronitrile 0.59
    3,7-dimethyl-1-octanol 0.7
    1-chlorooctane 0.32
    1-chlorotetradecane 0.2
    n-nonane 0.05
    undecane 0.06
    tert-butylcyclohexane 0.05
    cyclooctane 0.03
    cyclopentanol 0.36
    tetrahydropyran 0.82
    tert-amyl methyl ether 0.56
    2,5,8-trioxanonane 10.43
    1-hexene 0.08
    2-isopropoxyethanol 1.42
    2,2,2-trifluoroethanol 1.45
    methyl butyrate 1.61

    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