Cucurbitacin E

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  • Identifiers

    CAS number
    18444-66-1

    Molecular formula
    C32H44O8

    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]3C=C(C(=O)C4(C)C)O)C)C)C)O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Woody 56.94%
    Odorless 36.29%
    Dry 28.97%
    Mint 27.71%
    Cedar 26.28%
    Sweet 26.18%
    Amber 24.21%
    Floral 24.05%
    Spicy 22.08%
    Cooling 21.78%

     

    Flavor
    Bitter 87.95%
    Odorless 25.41%
    Bland 22.31%
    Cedarleaf 20.93%
    Sweet-like 20.69%
    Ripe apricot 19.83%
    Red fruit 19.62%
    Heather 19.59%
    Broom 19.55%
    Parsley 19.4%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.2

    pKa est.
    5.13 (weak acid)

    Molecular weight
    556.7 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Boiling point est.
    422°C

    Flash point

    • 270.68 ˚C est.

  • Synonyms

    • Cucurbitacin E
    • 18444-66-1
    • alpha-Elaterin
    • alpha-Elaterine
    • NSC 106399
    • NSC-106399
    • V8A45XYI21
    • NSC-521775
    • CHEBI:3944
    • [(E,6R)-6-[(8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl] acetate
    • DTXSID601030496
    • 19-Norlanosta-1,5,23-triene-3,11,22-trione, 25-(acetyloxy)-2,16,20-trihydroxy-9-methyl-, (9beta,10alpha,16alpha,23E)-
    • ((E,6R)-6-((8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-8,10,12,15,16,17-hexahydro-7H-cyclopenta(a)phenanthren-17-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl) acetate
    • RefChem:128717
    • DTXCID701529571
    • 242-325-2
    • ELATERIN, ALPHA
    • Cucurbitacine E
    • .alpha.-Elaterin
    • .alpha.-Elaterine
    • MFCD00135936
    • 19-Norlanosta-1,5,23-triene-3,11,22-trione,25-(acetyloxy)-2,16,20-trihydroxy-9-methyl-, (9b,10a,16a,23E)-
    • Cucurbitacine-E
    • (R,E)-6-((8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-4,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate
    • C32H44O8
    • CUE
    • UNII-V8A45XYI21
    • Cucurbitacin-E
    • NSC106399
    • 19-Nor-9.beta.,5,23-triene-3,11,22-trione, 2,16.alpha.,20,25-tetrahydroxy-9-methyl-, 25-acetate
    • 19-Norlanosta-1,23-triene-3,11,22-trione, 25-(acetyloxy)-2,16,20-trihydroxy-9-methyl-, (9.beta.,10.alpha.,16.alpha.,23E)-
    • EINECS 242-325-2
    • -Elaterin;-Elaterine
    • BRN 2343323
    • Cucurbitacin E (Standard)
    • CUCURBITACIN E [MI]
    • (-)-CUCURBITACIN E
    • SCHEMBL140616
    • orb1301289
    • Cucurbitacin E (alpha-Elaterin)
    • HY-N0417R
    • NDYMQXYDSVBNLL-MUYMLXPFSA-N
    • HY-N0417
    • LMST01010107
    • NSC521775
    • AKOS015896851
    • CS-3817
    • FC69737
    • 19-Norlanosta-1,5,23-triene-3,11,22-trione, 25-(acetyloxy)-2,16,20-trihydroxy-9-methyl-, (9.beta.,10.alpha.,16.alpha.,23E)-
    • 2,16alpha,20,25-Tetrahydroxy-9beta-methyl-10alpha,-19-norlanosta-1,5,23(E)-triene-3,11,22-trione 25-acetate
    • 25-(Acetyloxy)-2,16,20-trihydroxy-9-methyl-19-norlanosta-1,5,23-triene-3,11,22-trione (9beta,10alpha,16alpha,23E)-
    • AC-34285
    • AS-76174
    • DA-72424
    • NS00094068
    • C08797
    • 444C661
    • Q5192451
    • (23E)-25-acetyloxy-2,16alpha,20-trihydroxy-9beta-methyl-19-nor-10alpha-lanosta-1,5,23-triene-3,11,22-trione
    • (4R,23E)-2,16alpha,20-trihydroxy-9beta,10,14-trimethyl-1,11,22-trioxo-4,9-cyclo-9,10-secocholesta-2,5,23-trien-25-yl acetate
    • (9.BETA.,10.ALPHA.,16.ALPHA.,23E)-25-(ACETYLOXY)-2,16,20-TRIHYDROXY-9-METHYL-19-NORLANOSTA-1,5,23-TRIENE-3,11,22-TRIONE
    • [(E,5R)-5-[(8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthren-17-yl]-5-hydroxy-1,1-dimethyl-4-oxo-hex-2-enyl] acetate
    • 19-Nor-9-beta,10-alpha-lanosta-1,5,23-triene-3,11,22-trione, 2,16-alpha,20,25-tetrahydroxy-9-methyl-, 25-acetate
    • 19-Nor-9beta,10alpha-lanosta-1,5,23-triene-3,11,22-trione, 2,16alpha,20,25-tetrahydroxy-9-methyl-, 25-acetate
    • 2,16alpha,20,25-tetrahydroxy-9-methyl-19-nor-9beta,10alpha-lanosta-1,5,23-triene-3,11,22-trione 25-acetate
    • 18444-66-1

  • Applications

    Cucurbitacin E (CAS 18444-66-1) is a natural tetracyclic triterpenoid that is predominantly explored in research and development contexts rather than consumer products. In pharmaceutical and medicinal chemistry, it is investigated as a pharmacological lead with cytotoxic activity and is used in studies that probe mechanisms of apoptosis and effects on the cell cycle. In oncology research, it serves as a tool compound to explore mechanisms of action in cancer cell models. In chemical synthesis, it provides a scaffold for the semi-synthetic cucurbitacin derivatives and serves as a reference in derivative work. In analytical chemistry and plant metabolite profiling, it is used as a reference standard for LC-MS/GC analyses and to validate extraction protocols from Cucurbitaceae sources. In agricultural and plant science contexts, it is studied for its role as a natural defense metabolite and for understanding plant-insect interactions. These applications are primarily in research settings and are subject to local regulations and formulation limits; there are no routine consumer product applications.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 44.42
    methanol 97.32
    isopropanol 16.84
    water 0.06
    ethyl acetate 10.62
    n-propanol 33.98
    acetone 37.78
    n-butanol 13.97
    acetonitrile 11.63
    DMF 323.14
    toluene 4.06
    isobutanol 12.28
    1,4-dioxane 70.05
    methyl acetate 16.96
    THF 183.2
    2-butanone 24.24
    n-pentanol 9.44
    sec-butanol 8.53
    n-hexane 0.27
    ethylene glycol 18.28
    NMP 204.41
    cyclohexane 0.29
    DMSO 181.53
    n-butyl acetate 4.86
    n-octanol 2.33
    chloroform 46.19
    n-propyl acetate 6.33
    acetic acid 59.12
    dichloromethane 40.71
    cyclohexanone 31.91
    propylene glycol 29.15
    isopropyl acetate 5.27
    DMAc 156.6
    2-ethoxyethanol 54.33
    isopentanol 5.66
    n-heptane 0.14
    ethyl formate 14.19
    1,2-dichloroethane 19.3
    n-hexanol 5.96
    2-methoxyethanol 143.06
    isobutyl acetate 3.41
    tetrachloromethane 3.29
    n-pentyl acetate 5.34
    transcutol 32.24
    n-heptanol 3.76
    ethylbenzene 1.66
    MIBK 5.69
    2-propoxyethanol 63.73
    tert-butanol 6.73
    MTBE 3.77
    2-butoxyethanol 21.98
    propionic acid 22.48
    o-xylene 1.71
    formic acid 51.28
    diethyl ether 9.88
    m-xylene 1.7
    p-xylene 1.84
    chlorobenzene 5.6
    dimethyl carbonate 22.43
    n-octane 0.07
    formamide 64.28
    cyclopentanone 91.4
    2-pentanone 13.91
    anisole 6.78
    cyclopentyl methyl ether 18.41
    gamma-butyrolactone 105.2
    1-methoxy-2-propanol 76.75
    pyridine 45.77
    3-pentanone 11.15
    furfural 64.24
    n-dodecane 0.04
    diethylene glycol 56.41
    diisopropyl ether 0.92
    tert-amyl alcohol 4.71
    acetylacetone 19.6
    n-hexadecane 0.05
    acetophenone 7.94
    methyl propionate 21.65
    isopentyl acetate 3.67
    trichloroethylene 45.93
    n-nonanol 2.46
    cyclohexanol 5.73
    benzyl alcohol 10.93
    2-ethylhexanol 1.81
    isooctanol 2.24
    dipropyl ether 3.77
    1,2-dichlorobenzene 4.62
    ethyl lactate 7.44
    propylene carbonate 23.51
    n-methylformamide 119.55
    2-pentanol 3.89
    n-pentane 0.27
    1-propoxy-2-propanol 23.24
    1-methoxy-2-propyl acetate 13.11
    2-(2-methoxypropoxy) propanol 10.42
    mesitylene 0.67
    ε-caprolactone 28.02
    p-cymene 0.6
    epichlorohydrin 111.32
    1,1,1-trichloroethane 7.95
    2-aminoethanol 46.74
    morpholine-4-carbaldehyde 175.38
    sulfolane 132.24
    2,2,4-trimethylpentane 0.08
    2-methyltetrahydrofuran 32.06
    n-hexyl acetate 5.71
    isooctane 0.05
    2-(2-butoxyethoxy)ethanol 16.51
    sec-butyl acetate 2.89
    tert-butyl acetate 4.58
    decalin 0.15
    glycerin 51.57
    diglyme 35.92
    acrylic acid 31.17
    isopropyl myristate 1.08
    n-butyric acid 19.36
    acetyl acetate 7.61
    di(2-ethylhexyl) phthalate 2.96
    ethyl propionate 6.08
    nitromethane 104.64
    1,2-diethoxyethane 7.54
    benzonitrile 6.64
    trioctyl phosphate 1.81
    1-bromopropane 6.71
    gamma-valerolactone 165.67
    n-decanol 1.27
    triethyl phosphate 2.37
    4-methyl-2-pentanol 1.76
    propionitrile 11.09
    vinylene carbonate 27.54
    1,1,2-trichlorotrifluoroethane 77.5
    DMS 7.86
    cumene 0.82
    2-octanol 1.59
    2-hexanone 8.42
    octyl acetate 2.2
    limonene 0.86
    1,2-dimethoxyethane 62.88
    ethyl orthosilicate 2.11
    tributyl phosphate 1.72
    diacetone alcohol 11.59
    N,N-dimethylaniline 4.84
    acrylonitrile 21.77
    aniline 9.35
    1,3-propanediol 45.36
    bromobenzene 4.68
    dibromomethane 18.8
    1,1,2,2-tetrachloroethane 31.53
    2-methyl-cyclohexyl acetate 3.57
    tetrabutyl urea 3.37
    diisobutyl methanol 0.77
    2-phenylethanol 8.63
    styrene 1.97
    dioctyl adipate 2.89
    dimethyl sulfate 42.67
    ethyl butyrate 3.65
    methyl lactate 23.95
    butyl lactate 7.42
    diethyl carbonate 2.45
    propanediol butyl ether 18.26
    triethyl orthoformate 3.44
    p-tert-butyltoluene 0.57
    methyl 4-tert-butylbenzoate 7.39
    morpholine 109.22
    tert-butylamine 1.91
    n-dodecanol 0.66
    dimethoxymethane 126.59
    ethylene carbonate 18.02
    cyrene 27.22
    2-ethoxyethyl acetate 12.79
    2-ethylhexyl acetate 2.75
    1,2,4-trichlorobenzene 7.54
    4-methylpyridine 23.03
    dibutyl ether 1.56
    2,6-dimethyl-4-heptanol 0.77
    DEF 27.36
    dimethyl isosorbide 23.48
    tetrachloroethylene 21.19
    eugenol 9.99
    triacetin 8.1
    span 80 10.3
    1,4-butanediol 15.38
    1,1-dichloroethane 11.63
    2-methyl-1-pentanol 4.25
    methyl formate 70.47
    2-methyl-1-butanol 6.55
    n-decane 0.11
    butyronitrile 7.57
    3,7-dimethyl-1-octanol 1.38
    1-chlorooctane 0.72
    1-chlorotetradecane 0.17
    n-nonane 0.1
    undecane 0.06
    tert-butylcyclohexane 0.12
    cyclooctane 0.1
    cyclopentanol 16.88
    tetrahydropyran 28.04
    tert-amyl methyl ether 3.46
    2,5,8-trioxanonane 18.1
    1-hexene 1.37
    2-isopropoxyethanol 19.29
    2,2,2-trifluoroethanol 20.08
    methyl butyrate 8.52

    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