Cucurbitacin C

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  • Identifiers

    CAS number
    5988-76-1

    Molecular formula
    C32H48O8

    SMILES
    CC(=O)OC(C)(C)/C=C/C(=O)[C@@](C)([C@H]1[C@@H](C[C@@]2([C@@]1(CC(=O)[C@@]3([C@H]2CC=C4[C@H]3CC[C@@H](C4(C)C)O)CO)C)C)O)O

    Safety labels

  • Odor profile

    Fragrance
    Woody 62.2%
    Odorless 34.5%
    Mint 32.28%
    Amber 30.22%
    Dry 29.86%
    Cedar 28.81%
    Sweet 28.77%
    Balsamic 28.41%
    Cooling 27.31%
    Herbal 25.85%

     

    Flavor
    Bitter 86.97%
    Odorless 25.19%
    Bland 22.13%
    Sweet-like 21.24%
    Cedarleaf 21.05%
    Ripe apricot 19.54%
    Heather 19.54%
    Old wood 19.47%
    Broom 19.46%
    Red fruit 19.38%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.8

    pKa est.
    5.27 (weak acid)

    Molecular weight
    560.7 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Boiling point est.
    233°C

    Melting point expt.

    • 207-207.5 °C

    Flash point

    • 285.13 ˚C est.

  • Synonyms

    • CUCURBITACIN C
    • 5988-76-1
    • [(E,6R)-6-[(3S,8S,9R,10R,13R,14S,16R,17R)-3,16-dihydroxy-9-(hydroxymethyl)-4,4,13,14-tetramethyl-11-oxo-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl] acetate
    • Cucurbitacine (C)
    • DTXSID90208593
    • NSC-94744
    • 25-(Acetyloxy)-3,16,20-trihydroxy-9-(hydroxymethyl)-19-norlanosta-5,23-diene-11,22-dione
    • ((E,6R)-6-((3S,8S,9R,10R,13R,14S,16R,17R)-3,16-dihydroxy-9-(hydroxymethyl)-4,4,13,14-tetramethyl-11-oxo-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta(a)phenanthren-17-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl) acetate
    • 19-Nor-9-beta,10-alpha-lanosta-5,23-diene-11,22-dione, 3-beta,16-alpha,20,25-tetrahydroxy-9-(hydroxymethyl)-, 25-acetate
    • 19-Nor-9beta,10alpha-lanosta-5,23-diene-11,22-dione, 3beta,16alpha,20,25-tetrahydroxy-9-(hydroxymethyl)-, 25-acetate
    • 19-Norlanosta-5,23-diene-11,22-dione, 25-(acetyloxy)-3,16,20-trihydroxy-9-(hydroxymethyl)-, (3beta,9beta,10alpha,16alpha,23E)-
    • RefChem:579528
    • DTXCID40131084
    • 938A8MM70H
    • CHEBI:3942
    • SCHEMBL10307353
    • NSC94744
    • LMST01010105
    • C08795
    • Q27106262
    • (1S,4R,23E)-1,16alpha,20-Trihydroxy-9alpha-(hydroxymethyl)-10,14-dimethyl-11,22-dioxo-8beta-4,9-cyclo-9,10-secocholesta-5,23-dien-25-yl acetate
    • 19-nor-9.beta.,23-diene-11,22-dione, 3.beta.,16.alpha.,20,25-tetrahydroxy-9-(hydroxymethyl)-, 25-acetate
    • 19-Norlanosta-5,22-dione, 25-(acetyloxy)-3,16,20-trihydroxy-9-(hydroxymethyl)-, (3.beta.,9.beta.,10.alpha.,16.alpha.,23E)-
    • 5988-76-1

  • Applications

    Cucurbitacin C (CAS 5988-76-1) is a naturally occurring tetracyclic triterpenoid from the Cucurbitaceae family. In industry and research contexts it is primarily used as a bioactive natural product studied in pharmaceutical and agrochemical research, serving as a lead structure or tool compound to explore cytotoxic activity and signaling pathways associated with cucurbitacins. It is also employed in academic chemical biology as a research reference and may function as a synthetic intermediate or starting point for semi-synthesis of related cucurbitane derivatives. Additionally, Cucurbitacin C is used as an analytical reference material in analytical chemistry for methods profiling cucurbitacins in plant extracts, and its study informs chemical ecology investigations of plant defense interactions. Handling and use are typically laboratory-scale and subject to applicable regulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 41.39
    methanol 112.59
    isopropanol 11.1
    water 0.05
    ethyl acetate 6.4
    n-propanol 24.17
    acetone 31.53
    n-butanol 9.14
    acetonitrile 7.79
    DMF 265.74
    toluene 2.29
    isobutanol 7.81
    1,4-dioxane 52.13
    methyl acetate 10.36
    THF 147.07
    2-butanone 16.88
    n-pentanol 7.06
    sec-butanol 4.98
    n-hexane 0.16
    ethylene glycol 14.78
    NMP 142.66
    cyclohexane 0.18
    DMSO 166.59
    n-butyl acetate 3.57
    n-octanol 1.92
    chloroform 25.2
    n-propyl acetate 4.56
    acetic acid 46.56
    dichloromethane 23.43
    cyclohexanone 23.02
    propylene glycol 21.75
    isopropyl acetate 3.19
    DMAc 113.74
    2-ethoxyethanol 44.34
    isopentanol 3.62
    n-heptane 0.1
    ethyl formate 10.39
    1,2-dichloroethane 11.64
    n-hexanol 4.26
    2-methoxyethanol 117.25
    isobutyl acetate 2.54
    tetrachloromethane 1.9
    n-pentyl acetate 4.1
    transcutol 27.25
    n-heptanol 2.96
    ethylbenzene 1.03
    MIBK 3.97
    2-propoxyethanol 48.49
    tert-butanol 4.34
    MTBE 2.34
    2-butoxyethanol 18.4
    propionic acid 13.83
    o-xylene 0.99
    formic acid 46.16
    diethyl ether 6.09
    m-xylene 1.03
    p-xylene 1.21
    chlorobenzene 3.27
    dimethyl carbonate 13.49
    n-octane 0.05
    formamide 53.7
    cyclopentanone 65.78
    2-pentanone 9.46
    anisole 4.46
    cyclopentyl methyl ether 11.57
    gamma-butyrolactone 70.64
    1-methoxy-2-propanol 55.57
    pyridine 30.7
    3-pentanone 7.15
    furfural 44.69
    n-dodecane 0.03
    diethylene glycol 44.85
    diisopropyl ether 0.55
    tert-amyl alcohol 2.69
    acetylacetone 13.99
    n-hexadecane 0.03
    acetophenone 5.7
    methyl propionate 12.54
    isopentyl acetate 2.68
    trichloroethylene 25.65
    n-nonanol 1.96
    cyclohexanol 3.45
    benzyl alcohol 7.85
    2-ethylhexanol 1.24
    isooctanol 1.74
    dipropyl ether 2.52
    1,2-dichlorobenzene 2.75
    ethyl lactate 5.5
    propylene carbonate 15.24
    n-methylformamide 98.97
    2-pentanol 2.3
    n-pentane 0.16
    1-propoxy-2-propanol 16.64
    1-methoxy-2-propyl acetate 9.37
    2-(2-methoxypropoxy) propanol 8.82
    mesitylene 0.45
    ε-caprolactone 18.77
    p-cymene 0.41
    epichlorohydrin 68.59
    1,1,1-trichloroethane 4.0
    2-aminoethanol 38.13
    morpholine-4-carbaldehyde 130.25
    sulfolane 95.58
    2,2,4-trimethylpentane 0.05
    2-methyltetrahydrofuran 20.35
    n-hexyl acetate 4.42
    isooctane 0.03
    2-(2-butoxyethoxy)ethanol 14.34
    sec-butyl acetate 1.91
    tert-butyl acetate 3.07
    decalin 0.1
    glycerin 38.86
    diglyme 29.95
    acrylic acid 19.81
    isopropyl myristate 0.81
    n-butyric acid 11.88
    acetyl acetate 4.6
    di(2-ethylhexyl) phthalate 2.52
    ethyl propionate 3.81
    nitromethane 78.34
    1,2-diethoxyethane 5.75
    benzonitrile 4.65
    trioctyl phosphate 1.48
    1-bromopropane 3.6
    gamma-valerolactone 125.36
    n-decanol 1.01
    triethyl phosphate 1.68
    4-methyl-2-pentanol 1.09
    propionitrile 6.61
    vinylene carbonate 18.33
    1,1,2-trichlorotrifluoroethane 53.29
    DMS 5.36
    cumene 0.58
    2-octanol 1.19
    2-hexanone 6.24
    octyl acetate 1.69
    limonene 0.58
    1,2-dimethoxyethane 50.34
    ethyl orthosilicate 1.52
    tributyl phosphate 1.37
    diacetone alcohol 8.59
    N,N-dimethylaniline 3.4
    acrylonitrile 13.83
    aniline 5.51
    1,3-propanediol 35.33
    bromobenzene 2.61
    dibromomethane 10.89
    1,1,2,2-tetrachloroethane 18.38
    2-methyl-cyclohexyl acetate 2.71
    tetrabutyl urea 2.79
    diisobutyl methanol 0.53
    2-phenylethanol 6.41
    styrene 1.23
    dioctyl adipate 2.37
    dimethyl sulfate 26.01
    ethyl butyrate 2.63
    methyl lactate 16.26
    butyl lactate 5.93
    diethyl carbonate 1.7
    propanediol butyl ether 16.37
    triethyl orthoformate 2.48
    p-tert-butyltoluene 0.38
    methyl 4-tert-butylbenzoate 5.88
    morpholine 76.9
    tert-butylamine 1.12
    n-dodecanol 0.52
    dimethoxymethane 97.52
    ethylene carbonate 12.04
    cyrene 21.89
    2-ethoxyethyl acetate 9.74
    2-ethylhexyl acetate 2.01
    1,2,4-trichlorobenzene 4.21
    4-methylpyridine 14.78
    dibutyl ether 1.12
    2,6-dimethyl-4-heptanol 0.53
    DEF 16.66
    dimethyl isosorbide 18.27
    tetrachloroethylene 13.24
    eugenol 8.0
    triacetin 6.18
    span 80 8.37
    1,4-butanediol 12.56
    1,1-dichloroethane 6.16
    2-methyl-1-pentanol 2.97
    methyl formate 56.46
    2-methyl-1-butanol 4.02
    n-decane 0.08
    butyronitrile 4.8
    3,7-dimethyl-1-octanol 1.03
    1-chlorooctane 0.51
    1-chlorotetradecane 0.12
    n-nonane 0.07
    undecane 0.04
    tert-butylcyclohexane 0.08
    cyclooctane 0.07
    cyclopentanol 10.68
    tetrahydropyran 19.09
    tert-amyl methyl ether 2.03
    2,5,8-trioxanonane 15.49
    1-hexene 0.83
    2-isopropoxyethanol 15.06
    2,2,2-trifluoroethanol 13.64
    methyl butyrate 5.66

    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