Ginkgolide B

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  • Identifiers

    CAS number
    15291-77-7

    Molecular formula
    C20H24O10

    SMILES
    C[C@@H]1C(=O)O[C@@H]2[C@]1([C@@]34C(=O)O[C@H]5[C@]3([C@@H]2O)[C@@]6([C@@H](C5)C(C)(C)C)[C@H](C(=O)O[C@H]6O4)O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 59.47%
    Spicy 26.97%
    Sweet 25.84%
    Woody 24.28%
    Cooling 19.63%
    Mint 19.45%
    Lactonic 16.54%
    Milky 15.83%
    Dry 15.73%
    Burnt 14.74%

     

    Flavor
    Bitter 91.08%
    Bland 23.26%
    Cedarleaf 22.37%
    Sweet-like 22.08%
    Ripe apricot 19.62%
    Parsley 19.57%
    Red fruit 19.47%
    Lovage 19.2%
    Fenugreek 18.79%
    Leaves 18.5%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.4

    pKa est.
    4.67 (weak acid)

    Molecular weight
    424.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Boiling point est.
    2008°C

    Flash point

    • 196.94 ˚C est.

  • Synonyms

    • Ginkgolide B
    • Ginkgolides, ginkgolide B
    • 15291-77-7
    • DF149B9460
    • Ginkgolide A, 1-hydroxy-, (1beta)-
    • BN-52051
    • BN 52021
    • BN-52021
    • 5H-Dicyclopenta(b,c)furan-3,5a(6H)-diacetic acid, 6-tert-butyl-3a-carboxyhexahydro-alpha5a,1,2,3,5,8-hexahydroxy-alpha3-methyl-, tri-gamma-lactone
    • 9H-1,7a-(Epoxymethano)-1H,6aH-cyclopenta(c)furo(2,3-b)furo(3',2':3,4)cyclopenta(1,2-d)furan-5,9,12(4H)-trione, 3-(1,1-dimethylethyl)hexahydro-4,7b,11-trihydroxy-8-methyl-, (1R,3S,3aS,4R,6aR,7aR,7bR,8S,10aS,11R,11aR)-
    • CHEBI:5356
    • DTXSID70873223
    • RefChem:37693
    • DTXCID501529313
    • (1R,3R,8S,10R,13S,16S,17R)-8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo(8.7.2.0^(1,11).0^(3,7).0^(7,11).0^(13,17))nonadecane-5,15,18-trione
    • 8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo(8.7.2.01,11.03,7.07,11.013,17)nonadecane-5,15,18-trione
    • Gingkolide B
    • Bilobalide B
    • UNII-DF149B9460
    • BN 52051
    • GINKGOLIDE B [MI]
    • GINKGOLIDE B [WHO-DD]
    • SCHEMBL14029435
    • GINKGOLIDE A, 1-HYDROXY-, (1.BETA.)-
    • GINKGOLIDE B (CONSTITUENT OF GINKGO) [DSC]
    • 5H-DICYCLOPENTA(B,C)FURAN-3,5A(6H)-DIACETIC ACID, 6-TERT-BUTYL-3A-CARBOXYHEXAHYDRO-.ALPHA.5A,1,2,3,5,8-HEXAHYDROXY-.ALPHA.3-METHYL-, TRI-.GAMMA.-LACTONE
    • 9H-1,7a-(Epoxymethano)-1H,6aH-cyclopenta(c)furo(2,3-b)furo(3',2':3,4)cyclopenta(1,2-d)furan-5,9,12(4H)-trione, 3-(1,1-dimethylethyl)hexahydro-4,7b,11-trihydroxy-8-methyl-, (1R,3S,3aS,4R,6aR,7aR,7bR,8S,10aS,11R,11aR)-
    • 9H-1,7a-(Epoxymethano)-1H,6aH-cyclopenta(c)furo(2,3-b)furo(3',2':3,4)cyclopenta(1,2-d)furan-5,9,12(4H)-trione, 3-(1,1-dimethylethyl)hexahydro-4,7b,11-trihydroxy-8-methyl-, (1R-(1alpha,3beta,3aS*,4beta,6aalpha,7aalpha,7balpha,8alpha,10aalpha,11beta,11aR*))-
    • 15291-77-7

  • Applications

    Ginkgolide B (CAS 15291-77-7) is a diterpene trilactone isolated from Ginkgo biloba, with practical applications primarily in pharmaceutical and biomedical research as a pharmacologically active natural product, notably as a lead compound and tool for studying platelet-activating factor (PAF) receptor antagonism and related inflammatory pathways. In analytical chemistry, it is used as a reference standard for quantitative methods (HPLC/LC-MS) in quality control of ginkgo-derived extracts and natural product libraries. Chemically, it can serve as an intermediate or building block in the organic synthesis of complex diterpenoids, enabling structure-activity relationship studies. Additionally, it is evaluated as a research reagent in PAF-related biochemical assays and receptor-binding studies to characterize structure-activity relationships.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 29.8
    methanol 66.3
    isopropanol 21.36
    water 2.25
    ethyl acetate 40.07
    n-propanol 23.29
    acetone 88.35
    n-butanol 22.38
    acetonitrile 48.7
    DMF 202.03
    toluene 12.15
    isobutanol 14.5
    1,4-dioxane 74.78
    methyl acetate 51.79
    THF 171.55
    2-butanone 57.15
    n-pentanol 12.95
    sec-butanol 14.85
    n-hexane 0.55
    ethylene glycol 28.62
    NMP 274.36
    cyclohexane 1.54
    DMSO 298.43
    n-butyl acetate 27.3
    n-octanol 5.66
    chloroform 68.92
    n-propyl acetate 24.9
    acetic acid 150.74
    dichloromethane 64.01
    cyclohexanone 100.39
    propylene glycol 22.18
    isopropyl acetate 26.39
    DMAc 160.82
    2-ethoxyethanol 50.87
    isopentanol 15.88
    n-heptane 0.58
    ethyl formate 51.31
    1,2-dichloroethane 45.31
    n-hexanol 16.11
    2-methoxyethanol 130.73
    isobutyl acetate 13.35
    tetrachloromethane 12.05
    n-pentyl acetate 18.9
    transcutol 27.11
    n-heptanol 9.8
    ethylbenzene 5.22
    MIBK 23.98
    2-propoxyethanol 76.32
    tert-butanol 18.6
    MTBE 8.4
    2-butoxyethanol 36.38
    propionic acid 46.44
    o-xylene 7.55
    formic acid 144.24
    diethyl ether 15.11
    m-xylene 7.55
    p-xylene 6.45
    chlorobenzene 19.05
    dimethyl carbonate 58.35
    n-octane 0.32
    formamide 171.53
    cyclopentanone 169.65
    2-pentanone 45.19
    anisole 12.78
    cyclopentyl methyl ether 35.61
    gamma-butyrolactone 212.82
    1-methoxy-2-propanol 77.84
    pyridine 68.87
    3-pentanone 33.16
    furfural 171.37
    n-dodecane 0.27
    diethylene glycol 82.81
    diisopropyl ether 3.7
    tert-amyl alcohol 12.96
    acetylacetone 77.73
    n-hexadecane 0.32
    acetophenone 27.7
    methyl propionate 49.82
    isopentyl acetate 21.04
    trichloroethylene 103.09
    n-nonanol 6.01
    cyclohexanol 23.05
    benzyl alcohol 24.13
    2-ethylhexanol 7.98
    isooctanol 6.99
    dipropyl ether 8.1
    1,2-dichlorobenzene 19.83
    ethyl lactate 24.78
    propylene carbonate 94.08
    n-methylformamide 129.01
    2-pentanol 10.83
    n-pentane 0.75
    1-propoxy-2-propanol 36.19
    1-methoxy-2-propyl acetate 40.5
    2-(2-methoxypropoxy) propanol 21.45
    mesitylene 4.1
    ε-caprolactone 95.08
    p-cymene 4.65
    epichlorohydrin 165.45
    1,1,1-trichloroethane 32.54
    2-aminoethanol 32.92
    morpholine-4-carbaldehyde 201.43
    sulfolane 281.14
    2,2,4-trimethylpentane 0.37
    2-methyltetrahydrofuran 60.04
    n-hexyl acetate 18.28
    isooctane 0.28
    2-(2-butoxyethoxy)ethanol 25.17
    sec-butyl acetate 14.78
    tert-butyl acetate 21.28
    decalin 0.77
    glycerin 70.21
    diglyme 49.04
    acrylic acid 68.56
    isopropyl myristate 6.22
    n-butyric acid 62.1
    acetyl acetate 47.13
    di(2-ethylhexyl) phthalate 11.62
    ethyl propionate 22.47
    nitromethane 245.96
    1,2-diethoxyethane 12.08
    benzonitrile 30.55
    trioctyl phosphate 9.87
    1-bromopropane 14.95
    gamma-valerolactone 241.28
    n-decanol 4.05
    triethyl phosphate 13.2
    4-methyl-2-pentanol 6.78
    propionitrile 30.07
    vinylene carbonate 96.67
    1,1,2-trichlorotrifluoroethane 138.68
    DMS 30.12
    cumene 3.34
    2-octanol 4.85
    2-hexanone 26.04
    octyl acetate 10.04
    limonene 6.54
    1,2-dimethoxyethane 65.92
    ethyl orthosilicate 10.14
    tributyl phosphate 9.36
    diacetone alcohol 43.16
    N,N-dimethylaniline 9.96
    acrylonitrile 56.23
    aniline 23.87
    1,3-propanediol 55.18
    bromobenzene 16.7
    dibromomethane 35.3
    1,1,2,2-tetrachloroethane 66.5
    2-methyl-cyclohexyl acetate 19.27
    tetrabutyl urea 15.07
    diisobutyl methanol 4.01
    2-phenylethanol 28.68
    styrene 5.54
    dioctyl adipate 12.06
    dimethyl sulfate 117.13
    ethyl butyrate 18.8
    methyl lactate 63.24
    butyl lactate 18.99
    diethyl carbonate 14.83
    propanediol butyl ether 21.25
    triethyl orthoformate 13.17
    p-tert-butyltoluene 4.11
    methyl 4-tert-butylbenzoate 23.25
    morpholine 90.88
    tert-butylamine 5.67
    n-dodecanol 2.74
    dimethoxymethane 101.67
    ethylene carbonate 76.39
    cyrene 60.73
    2-ethoxyethyl acetate 29.26
    2-ethylhexyl acetate 16.82
    1,2,4-trichlorobenzene 27.33
    4-methylpyridine 53.89
    dibutyl ether 3.79
    2,6-dimethyl-4-heptanol 4.01
    DEF 60.11
    dimethyl isosorbide 50.03
    tetrachloroethylene 49.98
    eugenol 24.37
    triacetin 25.34
    span 80 21.42
    1,4-butanediol 20.91
    1,1-dichloroethane 32.17
    2-methyl-1-pentanol 10.77
    methyl formate 118.37
    2-methyl-1-butanol 14.35
    n-decane 0.47
    butyronitrile 28.32
    3,7-dimethyl-1-octanol 5.09
    1-chlorooctane 2.56
    1-chlorotetradecane 1.12
    n-nonane 0.38
    undecane 0.34
    tert-butylcyclohexane 0.5
    cyclooctane 0.6
    cyclopentanol 40.36
    tetrahydropyran 40.74
    tert-amyl methyl ether 8.66
    2,5,8-trioxanonane 32.14
    1-hexene 2.45
    2-isopropoxyethanol 28.19
    2,2,2-trifluoroethanol 92.73
    methyl butyrate 32.08

    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