Cucurbitacin I

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  • Identifiers

    CAS number
    2222-07-3

    Molecular formula
    C30H42O7

    SMILES
    C[C@@]12C[C@H]([C@@H]([C@]1(CC(=O)[C@@]3([C@H]2CC=C4[C@H]3C=C(C(=O)C4(C)C)O)C)C)[C@](C)(C(=O)/C=C/C(C)(C)O)O)O

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Woody 57.48%
    Odorless 35.4%
    Sweet 31.42%
    Dry 27.78%
    Mint 27.31%
    Cedar 24.73%
    Spicy 24.6%
    Amber 24.4%
    Balsamic 22.94%
    Camphoreous 22.61%

     

    Flavor
    Bitter 86.78%
    Odorless 25.55%
    Bland 21.52%
    Cedarleaf 21.25%
    Sweet-like 21.22%
    Ripe apricot 19.83%
    Red fruit 19.58%
    Heather 19.42%
    Parsley 19.35%
    Leaves 19.32%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.7

    pKa est.
    6.15 (neutral)

    Molecular weight
    514.6 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Boiling point est.
    412°C

    Flash point

    • 272.37 ˚C est.

  • Synonyms

    • Cucurbitacin I
    • 2222-07-3
    • Elatericin B
    • JSI-124
    • SHQ47990PH
    • NSC-112167
    • NSC-521777
    • CHEBI:3947
    • (8S,9R,10R,13R,14S,16R,17R)-17-[(E,2R)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,16-dihydroxy-4,4,9,13,14-pentamethyl-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthrene-3,11-dione
    • DTXSID501015546
    • (8S,9R,10R,13R,14S,16R,17R)-17-((E,2R)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-8,10,12,15,16,17-hexahydro-7H-cyclopenta(a)phenanthrene-3,11-dione
    • RefChem:579530
    • JSI124
    • DTXCID501473809
    • 218-736-8
    • 1,2-Dehydroelatericin A
    • Cucurbitacine (I)
    • 19-Nor-9-beta,10-alpha-lanosta-1,5,23-triene-3,11,22-trione, 9-methyl-2,16,20,25-tetrahydroxy-
    • MFCD09971044
    • NSC521777
    • (8S,9R,10R,13R,14S,16R,17R)-17-[(E,1R)-1,5-dihydroxy-1,5-dimethyl-2-oxo-hex-3-enyl]-2,16-dihydroxy-4,4,9,13,14-pentamethyl-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthrene-3,11-dione
    • 19-Norlanosta-1,5,23-triene-3,11,22-trione, 2,16,20,25-tetrahydroxy-9-methyl-, (9.beta.,10.alpha.,16.alpha.,23E)-
    • MLS002702902
    • 19-nor-9.beta.,5,23-triene-3,11,22-trione, 9-methyl-2,16,20,25-tetrahydroxy-
    • Elatericin B;JSI-124;NSC-521777
    • 19-Norlanosta-1,23-triene-3,11,22-trione, 2,16,20,25-tetrahydroxy-9-methyl-, (9.beta.,10.alpha.,16.alpha.)- (VA
    • EINECS 218-736-8
    • NSC 112167
    • NSC 521777
    • CUCURBITACCINE (I)
    • Cucurbitacin I (Standard)
    • UNII-SHQ47990PH
    • Cucurbitacin I (Elatericin B)
    • CHEMBL387737
    • orb1296138
    • SCHEMBL2523066
    • HY-N1405R
    • NISPVUDLMHQFRQ-MKIKIEMVSA-N
    • GLXC-10147
    • Cucurbitacin I - Bio-X trade mark
    • HY-N1405
    • LMST01010110
    • NSC112167
    • AKOS024456675
    • CS-5431
    • FC64989
    • NCGC00388208-02
    • 19-Norlanosta-1,5,23-triene-3,11,22-trione, 2,16,20,25-tetrahydroxy-9-methyl-, (9beta,10alpha,16alpha)-
    • 19-Norlanosta-1,5,23-triene-3,11,22-trione, 2,16,20,25-tetrahydroxy-9-methyl-, (9beta,10alpha,16alpha)- (VAN)
    • 2,16alpha,20,25-Tetrahydroxy-9beta-methyl-10alpha-19-norlanosta-1,5,23(E)-triene-3,11,22-trione
    • 28580-39-4
    • BC300056
    • MS-29560
    • XT170627
    • Elatericin B; JSI-124; NSC-521777
    • C08800
    • F85354
    • 222C073
    • Q27106265
    • 2,16a,20,25-Tetrahydroxy-9-methyl-19-Nor-9b,10a-lanosta-1,5,23-triene-3,11,22-trione
    • (4R,23E)-2,16alpha,20,25-Tetrahydroxy-9alpha,10,14-trimethyl-8beta-4,9-cyclo-9,10-secocholesta-2,5,23-triene-1,11,22-trione
    • (4R,9beta,16alpha,23E)-2,16,20,25-tetrahydroxy-9,10,14-trimethyl-4,9-cyclo-9,10-secocholesta-2,5,23-triene-1,11,22-trione
    • 2,16,20,25-Terahydroxycucurbita-1,5,23-triene-3,11,22-trione - Iberis umbellata (candytuft)
    • 2222-07-3

  • Applications

    Cucurbitacin I (CAS 2222-07-3) is a highly oxygenated triterpenoid isolated from cucurbitaceous plants. In practice, it is primarily encountered in pharmaceutical and biomedical research as a cytotoxic agent and as a modulator of cellular signaling pathways (notably JAK/STAT and related MAPK cascades). It is frequently used as a chemical scaffold for medicinal chemistry and SAR studies, and as a biochemical tool for studying signal transduction in cultured cells. In natural product chemistry, it is used as an isolable reference compound and for analytical method development (e.g., LC-MS quantification). Some studies have investigated its potential agrochemical properties, and it is sometimes evaluated for derivative libraries or synthetic accessibility, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 48.83
    methanol 104.26
    isopropanol 14.1
    water 0.04
    ethyl acetate 8.67
    n-propanol 30.24
    acetone 27.85
    n-butanol 11.69
    acetonitrile 7.84
    DMF 307.06
    toluene 3.2
    isobutanol 9.71
    1,4-dioxane 64.19
    methyl acetate 12.12
    THF 178.45
    2-butanone 17.54
    n-pentanol 8.37
    sec-butanol 6.22
    n-hexane 0.24
    ethylene glycol 15.92
    NMP 150.47
    cyclohexane 0.23
    DMSO 153.03
    n-butyl acetate 4.67
    n-octanol 2.51
    chloroform 30.39
    n-propyl acetate 5.59
    acetic acid 45.13
    dichloromethane 24.4
    cyclohexanone 24.87
    propylene glycol 25.8
    isopropyl acetate 4.98
    DMAc 120.08
    2-ethoxyethanol 53.81
    isopentanol 4.66
    n-heptane 0.15
    ethyl formate 10.54
    1,2-dichloroethane 12.2
    n-hexanol 6.61
    2-methoxyethanol 147.0
    isobutyl acetate 3.18
    tetrachloromethane 2.23
    n-pentyl acetate 5.62
    transcutol 33.01
    n-heptanol 4.34
    ethylbenzene 1.54
    MIBK 5.39
    2-propoxyethanol 73.1
    tert-butanol 5.26
    MTBE 3.18
    2-butoxyethanol 25.55
    propionic acid 15.03
    o-xylene 1.44
    formic acid 44.69
    diethyl ether 8.57
    m-xylene 1.58
    p-xylene 1.67
    chlorobenzene 3.89
    dimethyl carbonate 18.58
    n-octane 0.08
    formamide 54.81
    cyclopentanone 70.43
    2-pentanone 11.07
    anisole 6.46
    cyclopentyl methyl ether 17.5
    gamma-butyrolactone 81.09
    1-methoxy-2-propanol 78.25
    pyridine 37.63
    3-pentanone 8.24
    furfural 48.65
    n-dodecane 0.04
    diethylene glycol 61.08
    diisopropyl ether 0.9
    tert-amyl alcohol 3.39
    acetylacetone 17.34
    n-hexadecane 0.05
    acetophenone 7.32
    methyl propionate 17.03
    isopentyl acetate 3.77
    trichloroethylene 31.37
    n-nonanol 2.6
    cyclohexanol 4.23
    benzyl alcohol 10.23
    2-ethylhexanol 1.85
    isooctanol 2.6
    dipropyl ether 3.74
    1,2-dichlorobenzene 3.46
    ethyl lactate 7.28
    propylene carbonate 17.95
    n-methylformamide 109.67
    2-pentanol 3.2
    n-pentane 0.22
    1-propoxy-2-propanol 25.7
    1-methoxy-2-propyl acetate 13.97
    2-(2-methoxypropoxy) propanol 11.03
    mesitylene 0.69
    ε-caprolactone 21.74
    p-cymene 0.67
    epichlorohydrin 88.32
    1,1,1-trichloroethane 5.13
    2-aminoethanol 45.74
    morpholine-4-carbaldehyde 158.59
    sulfolane 104.09
    2,2,4-trimethylpentane 0.07
    2-methyltetrahydrofuran 26.46
    n-hexyl acetate 6.01
    isooctane 0.05
    2-(2-butoxyethoxy)ethanol 18.55
    sec-butyl acetate 2.6
    tert-butyl acetate 4.65
    decalin 0.14
    glycerin 47.1
    diglyme 36.48
    acrylic acid 21.05
    isopropyl myristate 1.11
    n-butyric acid 14.47
    acetyl acetate 6.07
    di(2-ethylhexyl) phthalate 3.08
    ethyl propionate 5.13
    nitromethane 76.45
    1,2-diethoxyethane 7.6
    benzonitrile 5.8
    trioctyl phosphate 1.93
    1-bromopropane 4.23
    gamma-valerolactone 142.01
    n-decanol 1.32
    triethyl phosphate 2.29
    4-methyl-2-pentanol 1.71
    propionitrile 7.67
    vinylene carbonate 20.78
    1,1,2-trichlorotrifluoroethane 65.96
    DMS 7.63
    cumene 0.82
    2-octanol 1.77
    2-hexanone 7.11
    octyl acetate 2.25
    limonene 0.89
    1,2-dimethoxyethane 57.24
    ethyl orthosilicate 2.11
    tributyl phosphate 1.78
    diacetone alcohol 12.04
    N,N-dimethylaniline 4.8
    acrylonitrile 15.25
    aniline 7.58
    1,3-propanediol 42.0
    bromobenzene 3.2
    dibromomethane 11.05
    1,1,2,2-tetrachloroethane 22.03
    2-methyl-cyclohexyl acetate 3.67
    tetrabutyl urea 3.34
    diisobutyl methanol 0.83
    2-phenylethanol 9.24
    styrene 1.82
    dioctyl adipate 2.88
    dimethyl sulfate 34.2
    ethyl butyrate 3.37
    methyl lactate 22.46
    butyl lactate 7.89
    diethyl carbonate 2.26
    propanediol butyl ether 20.43
    triethyl orthoformate 3.38
    p-tert-butyltoluene 0.65
    methyl 4-tert-butylbenzoate 8.08
    morpholine 103.72
    tert-butylamine 1.47
    n-dodecanol 0.68
    dimethoxymethane 129.77
    ethylene carbonate 14.05
    cyrene 26.74
    2-ethoxyethyl acetate 12.94
    2-ethylhexyl acetate 2.82
    1,2,4-trichlorobenzene 5.41
    4-methylpyridine 18.78
    dibutyl ether 1.49
    2,6-dimethyl-4-heptanol 0.83
    DEF 22.17
    dimethyl isosorbide 25.04
    tetrachloroethylene 15.63
    eugenol 10.84
    triacetin 8.16
    span 80 10.94
    1,4-butanediol 13.94
    1,1-dichloroethane 7.25
    2-methyl-1-pentanol 3.62
    methyl formate 59.12
    2-methyl-1-butanol 4.95
    n-decane 0.11
    butyronitrile 5.59
    3,7-dimethyl-1-octanol 1.47
    1-chlorooctane 0.65
    1-chlorotetradecane 0.15
    n-nonane 0.1
    undecane 0.06
    tert-butylcyclohexane 0.11
    cyclooctane 0.09
    cyclopentanol 12.85
    tetrahydropyran 23.73
    tert-amyl methyl ether 2.75
    2,5,8-trioxanonane 18.8
    1-hexene 1.2
    2-isopropoxyethanol 19.81
    2,2,2-trifluoroethanol 13.31
    methyl butyrate 7.22

    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