Glyceollin I

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  • Identifiers

    CAS number
    57103-57-8

    Molecular formula
    C20H18O5

    SMILES
    CC1(C=CC2=C(O1)C=CC3=C2OC[C@@]4([C@H]3OC5=C4C=CC(=C5)O)O)C

    Safety labels

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Sweet 48.09%
    Phenolic 41.45%
    Vanilla 33.46%
    Spicy 30.2%
    Powdery 27.53%
    Odorless 26.99%
    Creamy 25.28%
    Balsamic 22.8%
    Animal 22.11%
    Smoky 19.89%

     

    Flavor
    Bitter 94.79%
    Cedarleaf 19.85%
    Bland 19.59%
    Parsley 19.31%
    Sweet-like 19.3%
    Lovage 18.62%
    Ripe apricot 18.55%
    Red fruit 18.39%
    Eugenol 17.94%
    Indole 17.81%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.5

    pKa est.
    7.98 (neutral)

    Molecular weight
    338.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    879°C

    Flash point

    • 249.97 ˚C est.

  • Synonyms

    • glyceollin I
    • (-)-Glyceollin I
    • 57103-57-8
    • DTXSID10205726
    • (2S,10S)-17,17-dimethyl-3,12,18-trioxapentacyclo[11.8.0.02,10.04,9.014,19]henicosa-1(13),4(9),5,7,14(19),15,20-heptaene-6,10-diol
    • (2S,10S)-17,17-dimethyl-3,12,18-trioxapentacyclo(11.8.0.02,10.04,9.014,19)henicosa-1(13),4(9),5,7,14(19),15,20-heptaene-6,10-diol
    • RefChem:663202
    • GlyTouCan:G71590IF
    • DTXCID40128217
    • G71590IF
    • 17,17-dimethyl-3,12,18-trioxapentacyclo(11.8.0.02,10.04,9.014,19)henicosa-1(13),4(9),5,7,14(19),15,20-heptaene-6,10-diol
    • Glyceollin
    • 6461TV6UCH
    • 66241-09-6
    • (-) - glyceollin I
    • UNII-6461TV6UCH
    • Glyceollins
    • Glyceolin
    • (6aS,11aS)-2,2-dimethyl-2H,6H-[1]benzofuro[3,2-c]pyrano[2,3-h]chromene-6a,9(11aH)-diol
    • UNII-Y43CLK47RO
    • C01701
    • Y43CLK47RO
    • SCHEMBL364885
    • CHEMBL1774987
    • SCHEMBL29367936
    • SCHEMBL30816128
    • CHEBI:16470
    • Glyceollin I, II & III (mixture)
    • LMPK12070123
    • XG161768
    • (-)-Glyceollin I, II & III (mixture)
    • NS00126928
    • Q5572526
    • 2H,6H-Benzofuro(3,2-c)pyrano(2,3-h)(1)benzopyran-6a,9(11aH)-diol, 2,2-dimethyl-
    • (6aS,11aS)-2,2-Dimethyl-2H,6H-benzo[4,5]furo[2,3-d]benzo[1,2-b:5,6-b']dipyran-6a,9(11aH)-diol
    • 2H,6H-BENZOFURO(3,2-C)PYRANO(2,3-H)(1)BENZOPYRAN-6A,9(11AH)-DIOL, 2,2-DIMETHYL-, (6AS,11AS)-
    • 2H,6H-BENZOFURO(3,2-C)PYRANO(2,3-H)(1)BENZOPYRAN-6A,9(11AH)-DIOL, 2,2-DIMETHYL-, (6AS-CIS)-
    • 57103-57-8

  • Applications

    Glyceollin I (CAS 57103-57-8) is a soybean-derived phytoalexin that is primarily studied as a biochemical probe and potential lead in pharmaceutical research, with investigations focusing on in vitro antiestrogen activity and related anticancer mechanisms, as well as its role in modulating cell signaling pathways. In agricultural and crop-protection contexts, it is evaluated for triggering or mimicking plant defense responses and as a model compound for elicitor-based strategies to enhance resistance in crops. In natural product chemistry and analytical workflows, glyceollin I serves as an isolated reference compound and standard for isolation, characterization, quality control, and method development (e.g., HPLC/NMR) of glyceollins. In biotechnological and production research, it is explored in the context of biosynthetic studies and potential routes for sustainable production, including attempts to express or enhance glyceollin biosynthesis in plant or microbial systems. Its use is largely research-oriented and subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 5.32
    methanol 11.84
    isopropanol 6.57
    water 0.1
    ethyl acetate 26.85
    n-propanol 7.52
    acetone 53.55
    n-butanol 8.02
    acetonitrile 32.91
    DMF 101.63
    toluene 4.33
    isobutanol 6.48
    1,4-dioxane 48.12
    methyl acetate 30.07
    THF 107.88
    2-butanone 37.81
    n-pentanol 6.98
    sec-butanol 4.21
    n-hexane 0.16
    ethylene glycol 9.26
    NMP 70.08
    cyclohexane 0.37
    DMSO 164.04
    n-butyl acetate 22.54
    n-octanol 8.67
    chloroform 53.26
    n-propyl acetate 23.11
    acetic acid 55.79
    dichloromethane 35.77
    cyclohexanone 54.07
    propylene glycol 6.54
    isopropyl acetate 22.73
    DMAc 141.0
    2-ethoxyethanol 37.67
    isopentanol 9.8
    n-heptane 0.44
    ethyl formate 26.49
    1,2-dichloroethane 24.95
    n-hexanol 8.77
    2-methoxyethanol 69.73
    isobutyl acetate 21.0
    tetrachloromethane 3.38
    n-pentyl acetate 19.56
    transcutol 108.6
    n-heptanol 9.08
    ethylbenzene 2.41
    MIBK 23.66
    2-propoxyethanol 58.76
    tert-butanol 10.18
    MTBE 7.21
    2-butoxyethanol 34.68
    propionic acid 19.56
    o-xylene 3.27
    formic acid 34.03
    diethyl ether 9.48
    m-xylene 3.65
    p-xylene 4.03
    chlorobenzene 9.43
    dimethyl carbonate 38.88
    n-octane 0.32
    formamide 51.17
    cyclopentanone 74.39
    2-pentanone 29.29
    anisole 13.79
    cyclopentyl methyl ether 21.06
    gamma-butyrolactone 83.96
    1-methoxy-2-propanol 51.77
    pyridine 29.89
    3-pentanone 24.54
    furfural 67.27
    n-dodecane 0.64
    diethylene glycol 63.3
    diisopropyl ether 4.04
    tert-amyl alcohol 6.21
    acetylacetone 55.2
    n-hexadecane 0.77
    acetophenone 23.09
    methyl propionate 31.15
    isopentyl acetate 23.85
    trichloroethylene 65.11
    n-nonanol 10.13
    cyclohexanol 8.7
    benzyl alcohol 15.99
    2-ethylhexanol 8.07
    isooctanol 9.0
    dipropyl ether 11.08
    1,2-dichlorobenzene 11.91
    ethyl lactate 25.57
    propylene carbonate 39.99
    n-methylformamide 47.24
    2-pentanol 4.79
    n-pentane 0.18
    1-propoxy-2-propanol 37.94
    1-methoxy-2-propyl acetate 46.39
    2-(2-methoxypropoxy) propanol 43.61
    mesitylene 2.6
    ε-caprolactone 44.27
    p-cymene 4.68
    epichlorohydrin 91.29
    1,1,1-trichloroethane 16.87
    2-aminoethanol 11.29
    morpholine-4-carbaldehyde 103.38
    sulfolane 97.93
    2,2,4-trimethylpentane 0.25
    2-methyltetrahydrofuran 24.69
    n-hexyl acetate 23.42
    isooctane 0.26
    2-(2-butoxyethoxy)ethanol 51.34
    sec-butyl acetate 17.29
    tert-butyl acetate 24.33
    decalin 0.47
    glycerin 28.64
    diglyme 96.83
    acrylic acid 26.84
    isopropyl myristate 13.45
    n-butyric acid 29.37
    acetyl acetate 31.62
    di(2-ethylhexyl) phthalate 16.31
    ethyl propionate 23.83
    nitromethane 133.16
    1,2-diethoxyethane 31.25
    benzonitrile 22.38
    trioctyl phosphate 12.98
    1-bromopropane 6.99
    gamma-valerolactone 120.82
    n-decanol 7.96
    triethyl phosphate 18.51
    4-methyl-2-pentanol 6.12
    propionitrile 26.66
    vinylene carbonate 49.92
    1,1,2-trichlorotrifluoroethane 76.04
    DMS 31.91
    cumene 2.49
    2-octanol 5.64
    2-hexanone 23.57
    octyl acetate 16.52
    limonene 5.62
    1,2-dimethoxyethane 76.87
    ethyl orthosilicate 16.14
    tributyl phosphate 15.06
    diacetone alcohol 35.58
    N,N-dimethylaniline 10.62
    acrylonitrile 45.39
    aniline 11.18
    1,3-propanediol 21.91
    bromobenzene 8.57
    dibromomethane 16.92
    1,1,2,2-tetrachloroethane 46.81
    2-methyl-cyclohexyl acetate 21.85
    tetrabutyl urea 21.54
    diisobutyl methanol 6.5
    2-phenylethanol 19.23
    styrene 2.99
    dioctyl adipate 22.3
    dimethyl sulfate 58.25
    ethyl butyrate 21.74
    methyl lactate 34.89
    butyl lactate 22.98
    diethyl carbonate 19.6
    propanediol butyl ether 26.94
    triethyl orthoformate 22.4
    p-tert-butyltoluene 4.47
    methyl 4-tert-butylbenzoate 27.93
    morpholine 49.06
    tert-butylamine 3.74
    n-dodecanol 6.36
    dimethoxymethane 86.71
    ethylene carbonate 45.78
    cyrene 46.02
    2-ethoxyethyl acetate 34.7
    2-ethylhexyl acetate 18.4
    1,2,4-trichlorobenzene 17.11
    4-methylpyridine 23.15
    dibutyl ether 11.2
    2,6-dimethyl-4-heptanol 6.5
    DEF 37.65
    dimethyl isosorbide 67.39
    tetrachloroethylene 25.4
    eugenol 29.47
    triacetin 36.99
    span 80 26.68
    1,4-butanediol 9.25
    1,1-dichloroethane 17.2
    2-methyl-1-pentanol 7.66
    methyl formate 47.16
    2-methyl-1-butanol 6.76
    n-decane 0.92
    butyronitrile 19.31
    3,7-dimethyl-1-octanol 9.85
    1-chlorooctane 4.48
    1-chlorotetradecane 2.44
    n-nonane 0.64
    undecane 0.75
    tert-butylcyclohexane 0.4
    cyclooctane 0.22
    cyclopentanol 10.25
    tetrahydropyran 22.13
    tert-amyl methyl ether 6.78
    2,5,8-trioxanonane 74.22
    1-hexene 0.9
    2-isopropoxyethanol 27.87
    2,2,2-trifluoroethanol 26.41
    methyl butyrate 29.63

    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