Bilobalide

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  • Identifiers

    CAS number
    33570-04-6

    Molecular formula
    C15H18O8

    SMILES
    CC(C)(C)[C@@]1(C[C@H]2[C@@]3([C@]14[C@H](C(=O)O[C@H]4OC3=O)O)CC(=O)O2)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 43.45%
    Sweet 35.5%
    Spicy 29.88%
    Woody 28.24%
    Mint 26.88%
    Herbal 22.7%
    Lactonic 22.48%
    Nutty 21.5%
    Tobacco 21.43%
    Cooling 19.77%

     

    Flavor
    Bitter 89.61%
    Bland 22.46%
    Cedarleaf 21.88%
    Sweet-like 21.59%
    Ripe apricot 20.23%
    Red fruit 20.0%
    Parsley 19.77%
    Cotton candy 19.6%
    Fenugreek 19.58%
    Extremely sweet 19.2%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.3

    pKa est.
    5.48 (weak acid)

    Molecular weight
    326.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1743°C

    Flash point

    • 186.5 ˚C est.

  • Synonyms

    • Bilobalide
    • 33570-04-6
    • Bilobalid
    • M81D2O8H7U
    • CHEBI:3103
    • DTXSID10873207
    • (1S,4R,7R,8S,9R,11S)-9-tert-butyl-7,9-dihydroxy-3,5,12-trioxatetracyclo[6.6.0.01,11.04,8]tetradecane-2,6,13-trione
    • 4H,5aH,9H-furo(2,3-b)furo(3',2':2,3)cyclopenta(1,2-c)furan-2,4,7(3H,8H)-trione, 9-(1,1-dimethylethyl)-10,10a-dihydro-8,9-dihydroxy-, (3aS,5aR,8R,8aS,9R,10aS)-
    • (1S,4R,7R,8S,9R,11S)-9-tert-butyl-7,9-dihydroxy-3,5,12-trioxatetracyclo[6.6.0.0^{1,11}.0^{4,8}]tetradecane-2,6,13-trione
    • (3aS,8R,8aS,9R,10aS)-9-tert-butyl-8,9-dihydroxydihydro-9H-furo[2,3-b]furo[3',2':2,3]cyclopenta[1,2-c]furan-2,4,7(3H,8H)-trione
    • 4H,5aH,9H-Furo[2,3-b]furo[3',2':2,3]cyclopenta[1,2-c]furan-2,4,7(3H,8H)-trione, 9-(1,1-dimethylethyl)-10,10a-dihydro-8,9-dihydroxy-, (3aS,5aR,8R,8aS,9R,10aS)-
    • (1S,4R,7R,8S,9R,11S)-9-tert-butyl-7,9-dihydroxy-3,5,12-trioxatetracyclo(6.6.0.0^(1,11).0^(4,8))tetradecane-2,6,13-trione
    • (1S,4R,7R,8S,9R,11S)-9-tert-butyl-7,9-dihydroxy-3,5,12-trioxatetracyclo(6.6.0.01,11.04,8)tetradecane-2,6,13-trione
    • (3aS,8R,8aS,9R,10aS)-9-tert-butyl-8,9-dihydroxydihydro-9H-furo(2,3-b)furo(3',2':2,3)cyclopenta(1,2-c)furan-2,4,7(3H,8H)-trione
    • RefChem:29988
    • DTXCID001765201
    • 608-892-9
    • (-)-Bilobalide
    • Bilobalide A
    • MFCD00238547
    • tert-butyl(dihydroxy)[?]trione
    • UNII-M81D2O8H7U
    • Bilobalide?
    • Bilobalide (NIST)
    • MFCD00132880
    • Bilobalide (Standard)
    • (-)-Bilobalide from Ginkgo biloba leaves
    • BILOBALIDE [MI]
    • BILOBALIDE [WHO-DD]
    • MLS000563448
    • SCHEMBL285824
    • GTPL2366
    • orb1304993
    • CHEMBL1318117
    • HY-N0076R
    • MOLPUWBMSBJXER-YDGSQGCISA-N
    • HMS2205O12
    • EX-A6793
    • HY-N0076
    • AKOS024282583
    • CCG-208160
    • CS-1517
    • EBC-616289
    • FB65801
    • NCGC00142501-01
    • NCGC00142501-02
    • 4H,5aH,9H-Furo(2,3-b)furo(3',2':2,3)cyclopenta(1,2-c)furan-2,4,7(3H,8H)-trione, 9-(1,1-dimethylethyl)-10,10a-dihydro-8,9-dihydroxy-, (5aR-(3aS*,5aalpha,8beta,8aS*,9alpha,10aalpha))-
    • AS-17551
    • SMR000232342
    • ST057155
    • SY075000
    • BILOBALIDE (CONSTITUENT OF GINKGO) [DSC]
    • 570B046
    • Q418459
    • SR-01000712074
    • SR-01000712074-4
    • (-)-Bilobalide from Ginkgo biloba leaves, >=93% (HPLC)
    • (1S,8S,12S,5R,14R)-14-(tert-butyl)-2,14-dihydroxy-4,6,11-trioxatetracyclo[6.6. 0.0<1,5>.0<8,12>]tetradecane-3,7,10-trione
    • (3aS,5aR,8R,8aS,9R,10aS)-9-tert-Butyl-8,9-dihydroxydihydro-4H,5aH,9H-furo[2,3-b]furo[3',2':2,3]cyclopenta[1,2-c]furan-2,4,7(3H,8H)-trione
    • 4H,5aH,9H-Furo[2,3-b]furo[3',2':2,3]cyclopenta[1,2-c]furan-2,4,7(3H,8H)-trione, 9-(1,1-dimethylethyl)-10,10a-dihydro-8,9-dihydroxy-,(3aS,5aR,8R,8aS,9R,10aS)-
    • 33570-04-6

  • Applications

    Bilobalide (CAS 33570-04-6) is used primarily as an analytical reference and standard in quality control of Ginkgo biloba extracts, enabling LC-MS/HPLC profiling of its terpenoid constituents. It also serves as a research building block in natural product chemistry, providing a platform for method development and synthetic exploration of terpenoid trilactones. In nutraceutical contexts, bilobalide is a constituent of standardized Ginkgo biloba extracts and may appear in dietary supplement formulations derived from those extracts. It is commonly employed in academic and industrial studies as a benchmark for analytical methods, investigations into biosynthesis, and structure–activity research of bilobalide and related compounds. Additionally, formulation scientists may consider bilobalide in cosmetic research as a plant-derived constituent, subject to regulatory controls.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 21.11
    methanol 64.02
    isopropanol 11.06
    water 2.68
    ethyl acetate 49.21
    n-propanol 11.79
    acetone 91.03
    n-butanol 9.07
    acetonitrile 66.78
    DMF 219.7
    toluene 10.11
    isobutanol 6.61
    1,4-dioxane 80.94
    methyl acetate 65.02
    THF 214.69
    2-butanone 52.35
    n-pentanol 5.67
    sec-butanol 7.34
    n-hexane 0.45
    ethylene glycol 26.69
    NMP 328.92
    cyclohexane 1.09
    DMSO 462.31
    n-butyl acetate 29.11
    n-octanol 4.62
    chloroform 89.64
    n-propyl acetate 27.22
    acetic acid 95.64
    dichloromethane 100.61
    cyclohexanone 76.62
    propylene glycol 13.65
    isopropyl acetate 27.22
    DMAc 203.62
    2-ethoxyethanol 43.51
    isopentanol 7.51
    n-heptane 0.49
    ethyl formate 54.18
    1,2-dichloroethane 59.4
    n-hexanol 9.01
    2-methoxyethanol 123.23
    isobutyl acetate 12.21
    tetrachloromethane 14.16
    n-pentyl acetate 15.08
    transcutol 29.79
    n-heptanol 6.07
    ethylbenzene 5.77
    MIBK 22.23
    2-propoxyethanol 65.7
    tert-butanol 11.35
    MTBE 6.95
    2-butoxyethanol 28.37
    propionic acid 33.71
    o-xylene 7.43
    formic acid 151.45
    diethyl ether 15.15
    m-xylene 7.0
    p-xylene 7.43
    chlorobenzene 20.44
    dimethyl carbonate 78.64
    n-octane 0.24
    formamide 233.13
    cyclopentanone 175.27
    2-pentanone 37.91
    anisole 21.47
    cyclopentyl methyl ether 37.59
    gamma-butyrolactone 262.6
    1-methoxy-2-propanol 68.92
    pyridine 83.86
    3-pentanone 30.53
    furfural 227.72
    n-dodecane 0.2
    diethylene glycol 78.7
    diisopropyl ether 3.82
    tert-amyl alcohol 7.94
    acetylacetone 92.52
    n-hexadecane 0.26
    acetophenone 37.82
    methyl propionate 58.3
    isopentyl acetate 21.24
    trichloroethylene 146.47
    n-nonanol 4.64
    cyclohexanol 10.73
    benzyl alcohol 20.12
    2-ethylhexanol 5.74
    isooctanol 4.45
    dipropyl ether 7.97
    1,2-dichlorobenzene 26.35
    ethyl lactate 26.79
    propylene carbonate 110.92
    n-methylformamide 148.09
    2-pentanol 5.08
    n-pentane 0.43
    1-propoxy-2-propanol 31.8
    1-methoxy-2-propyl acetate 49.36
    2-(2-methoxypropoxy) propanol 23.31
    mesitylene 4.26
    ε-caprolactone 80.71
    p-cymene 4.97
    epichlorohydrin 221.19
    1,1,1-trichloroethane 39.08
    2-aminoethanol 23.82
    morpholine-4-carbaldehyde 220.52
    sulfolane 366.34
    2,2,4-trimethylpentane 0.27
    2-methyltetrahydrofuran 60.28
    n-hexyl acetate 16.47
    isooctane 0.2
    2-(2-butoxyethoxy)ethanol 22.28
    sec-butyl acetate 15.0
    tert-butyl acetate 26.06
    decalin 0.73
    glycerin 52.7
    diglyme 61.78
    acrylic acid 52.56
    isopropyl myristate 5.76
    n-butyric acid 35.19
    acetyl acetate 58.94
    di(2-ethylhexyl) phthalate 11.04
    ethyl propionate 30.47
    nitromethane 325.47
    1,2-diethoxyethane 12.15
    benzonitrile 30.69
    trioctyl phosphate 8.36
    1-bromopropane 13.49
    gamma-valerolactone 243.68
    n-decanol 3.11
    triethyl phosphate 16.83
    4-methyl-2-pentanol 3.96
    propionitrile 30.35
    vinylene carbonate 107.66
    1,1,2-trichlorotrifluoroethane 171.07
    DMS 39.97
    cumene 3.72
    2-octanol 3.11
    2-hexanone 22.28
    octyl acetate 8.68
    limonene 6.0
    1,2-dimethoxyethane 81.2
    ethyl orthosilicate 12.16
    tributyl phosphate 8.74
    diacetone alcohol 41.84
    N,N-dimethylaniline 13.65
    acrylonitrile 67.59
    aniline 19.81
    1,3-propanediol 33.92
    bromobenzene 20.46
    dibromomethane 46.01
    1,1,2,2-tetrachloroethane 88.66
    2-methyl-cyclohexyl acetate 20.03
    tetrabutyl urea 15.18
    diisobutyl methanol 3.36
    2-phenylethanol 26.04
    styrene 6.24
    dioctyl adipate 11.51
    dimethyl sulfate 173.88
    ethyl butyrate 21.63
    methyl lactate 63.79
    butyl lactate 16.35
    diethyl carbonate 20.61
    propanediol butyl ether 15.25
    triethyl orthoformate 14.37
    p-tert-butyltoluene 4.29
    methyl 4-tert-butylbenzoate 26.81
    morpholine 81.88
    tert-butylamine 3.56
    n-dodecanol 2.1
    dimethoxymethane 130.96
    ethylene carbonate 81.73
    cyrene 63.64
    2-ethoxyethyl acetate 27.3
    2-ethylhexyl acetate 16.8
    1,2,4-trichlorobenzene 34.66
    4-methylpyridine 56.55
    dibutyl ether 3.43
    2,6-dimethyl-4-heptanol 3.36
    DEF 58.42
    dimethyl isosorbide 70.84
    tetrachloroethylene 66.13
    eugenol 27.25
    triacetin 24.99
    span 80 16.35
    1,4-butanediol 11.22
    1,1-dichloroethane 33.15
    2-methyl-1-pentanol 5.39
    methyl formate 155.38
    2-methyl-1-butanol 6.43
    n-decane 0.36
    butyronitrile 22.62
    3,7-dimethyl-1-octanol 4.52
    1-chlorooctane 2.47
    1-chlorotetradecane 0.95
    n-nonane 0.3
    undecane 0.26
    tert-butylcyclohexane 0.47
    cyclooctane 0.46
    cyclopentanol 22.13
    tetrahydropyran 33.21
    tert-amyl methyl ether 7.73
    2,5,8-trioxanonane 37.9
    1-hexene 1.87
    2-isopropoxyethanol 21.53
    2,2,2-trifluoroethanol 83.6
    methyl butyrate 36.73

    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